Transcript of Jon Stewart Interview: Politics, Anxiety, and Finding Hope in the Chaos on IMO Podcast

So I apologize. I don’t know what they told you. I don’t know how much they charge, but you, you’re living in a hotel. Airbnb.

MICHELLE OBAMA: (00:04:46 – 00:04:47) Yeah. Oh my God.

JON STEWART: (00:04:47 – 00:04:49) But have fun. Yeah.

CRAIG ROBINSON: (00:04:49 – 00:04:49) Yeah.

MICHELLE OBAMA: (00:04:49 – 00:04:51) How, how are you doing? How are, how are you?

JON STEWART: (00:04:53 – 00:04:56) Guys doing? It’s, it’s lovely to see all you guys look great.

CRAIG ROBINSON: (00:04:56 – 00:04:57) Thank you.

JON STEWART: (00:04:57 – 00:05:00) You look rested. You look healthy. I feel healthy.

CRAIG ROBINSON: (00:05:00 – 00:05:03) But you’re doing better than we are because you’re only working one day a week.

JON STEWART: (00:05:03 – 00:05:04) Let me tell you something. That’s the—

MICHELLE OBAMA: (00:05:04 – 00:05:10) if I had known that, if I had known that, that, like, the daily thing is kind of a ripoff.

JON STEWART: (00:05:10 – 00:05:16) It kind of— it ground you down to a nub a little bit. But this one day a week thing has been revelatory.

MICHELLE OBAMA: (00:05:16 – 00:05:35) I can’t— that when I look at, you know, talk shows, comedians, folks who are on every night. I can’t imagine. That’s the first thing. Ellen used to say, “You should do a talk show. You should do—” I was like, there’s— why? Why would I go from what I was doing to another thing that is really scary and hard?

JON STEWART: (00:05:35 – 00:05:57) It’s hard for me to explain to you the kind of pressure that comedians and talk show hosts face. It’s not something I don’t think you’d be able to bear up to. And so I agree. There’s a lot of times a lot of people say, “What’s the most important job in the world?” And they go, “I don’t know, whoever took over for Ellen.”

MICHELLE OBAMA: (00:06:00 – 00:06:08) But it is hard. I mean, you’ve got to come up with something. You’ve got to have an opinion about the world every day, especially your commentary.

JON STEWART: (00:06:08 – 00:06:52) But not hard. It’s a real gift for performers when you come up. You know, there really is— there’s a ladder, and you really do make your bones doing the hard work, the kind of grunt work of comedy, like driving from Rochester to Buffalo and then down again over to Hartford and doing all those comedy clubs and all that.

So when the opportunity ever presents itself for a regular gig where you can live in one place and maybe raise a family, it really does. It feels like kind of you made it to the island. You’ve been in the life raft, but you kind of made it to the island doing that whole thing.

Family and Childhood

MICHELLE OBAMA: (00:06:53 – 00:06:58) Now, did your mother say, “Well, that’s wonderful, Jon. I’m so glad that you are—”

JON STEWART: (00:06:58 – 00:07:06) It’s an interesting question. And also that idea of like, you know, did your parents encourage you? And I was like, “Now say that again. What’s that?”

MICHELLE OBAMA: (00:07:06 – 00:07:06) What is that word?

JON STEWART: (00:07:06 – 00:07:14) Encourage? I mean, they knew I lived in the house. Yeah. But— and I also, I had the advantage of my parents split when I was probably 10 years old.

MICHELLE OBAMA: (00:07:14 – 00:07:15) Yeah.

JON STEWART: (00:07:15 – 00:07:18) So at that point, you really are.

MICHELLE OBAMA: (00:07:18 – 00:07:19) Your mom was holding it down.

JON STEWART: (00:07:20 – 00:07:20) She was holding it down.

MICHELLE OBAMA: (00:07:20 – 00:07:20) Yeah.

JON STEWART: (00:07:21 – 00:07:23) Her mantra was, “We will not lose the house.”

MICHELLE OBAMA: (00:07:23 – 00:07:23) Yes.

JON STEWART: (00:07:24 – 00:07:45) Because we had— this was ’71, ’72. So this was just in that era of I’m Okay, You’re Okay, The Feminine Mystique. Suddenly there was a consciousness in America for women that, oh, if my husband is an ass, I don’t have to take that. Right. So that’s what happened.

MICHELLE OBAMA: (00:07:46 – 00:07:47) Had she worked before?

JON STEWART: (00:07:48 – 00:07:56) Was she a stay-at-home mom? She was a special ed teacher. So she taught gifted program, special ed program. She was a teacher. And then she’d also taught younger kids.

MICHELLE OBAMA: (00:07:56 – 00:07:56) Yeah.

JON STEWART: (00:07:57 – 00:08:25) Had done that in New York City, in the Bronx, where she grew up, in Washington Heights as well. She did it for a little bit in El Paso when my dad was in the Army. She taught in Texas for a little bit and then a little bit when she came back. But so we were only— there was only— we only knew of two families that had divorces. And the other family lost the house.

CRAIG ROBINSON: (00:08:26 – 00:08:26) Yeah.

JON STEWART: (00:08:27 – 00:08:46) So we weren’t going to lose the house. And she, to her credit, didn’t lose the house. Put it on her shoulders and went out and became what they called a teacher of teachers. She began to give seminars to other teachers, and then became like an assistant principal, and then— and really worked her way through there.

MICHELLE OBAMA: (00:08:47 – 00:09:02) Did you— could you— did you know that about your mom when you were young? At 10, when your dad left and he left you all high and dry, did you understand the situation that you guys were in at the time? Were you—

JON STEWART: (00:09:02 – 00:09:14) I was glad that the— honestly, like, that the yelling had stopped. I mean, honestly, it’s one of the greatest things about— it sounds counterintuitive to talk about one of the best things about divorce. Let me tell you something.

MICHELLE OBAMA: (00:09:15 – 00:09:15) Yeah.

JON STEWART: (00:09:15 – 00:09:18) If you’re ever in this position, get yourself one of these divorces.

MICHELLE OBAMA: (00:09:18 – 00:09:19) They’re fantastic.

JON STEWART: (00:09:21 – 00:09:25) You know that feeling when you’re trying to sleep and a car alarm is going off?

CRAIG ROBINSON: (00:09:26 – 00:09:26) Yeah.

JON STEWART: (00:09:27 – 00:09:37) And there’s no real rhythm to it. You can’t quite get into it. You can’t even use it as white noise. The feeling that you get in your soul when it stops. Yeah, that’s what it was like.

MICHELLE OBAMA: (00:09:37 – 00:09:37) Right.

CRAIG ROBINSON: (00:09:38 – 00:09:38) Okay.

JON STEWART: (00:09:38 – 00:09:49) But I was— I wasn’t aware of the psychological trauma that she had been taking, that you’re just glad the noise has stopped.

CRAIG ROBINSON: (00:09:50 – 00:09:54) See, I was going to ask you which one of them is funny, but now that doesn’t seem appropriate.

JON STEWART: (00:09:55 – 00:09:59) The one that drank. See if you can guess.

CRAIG ROBINSON: (00:10:02 – 00:10:10) But do you think your humor developed out of sort of as a coping mechanism, or were they funny?

JON STEWART: (00:10:12 – 00:10:16) My grandfather probably was a pretty funny guy, but I don’t—

MICHELLE OBAMA: (00:10:16 – 00:10:17) Your maternal grandfather?

JON STEWART: (00:10:17 – 00:11:14) My maternal grandfather, Nathan. My son is named after him, and he was just a character. Lived to be 94, died when he got a stroke playing poker with his friends in an OTB at 94 years old, smoking. He’s just one of those dudes. Born in China, raised in China. Family was wealthy till the Japanese took over China, and then they had nothing.

And he, you know, he used to say to me, “When I had the money, I lived very well, but without money, I did not.” And I was like, that sounds right. Yeah. But so— but I mean, it’s like anything else. I think sometimes I think it’s just how I’m wired. And I don’t know that it was a response to anything more than it was just these are the genetic wirings that I’ve been given.

MICHELLE OBAMA: (00:11:15 – 00:11:20) Your relationship with your siblings, were you guys tight growing up?

JON STEWART: (00:11:21 – 00:11:38) Well, so I have two. So my father had two others. So he remarried. And then I have an older brother, and we have a very good relationship. So we’re very close. But I never lived with the other guys. And it was born of such complexity. I don’t know how your family’s history is run, but like—

MICHELLE OBAMA: (00:11:38 – 00:11:43) Oh, everybody’s got a history. It’s gnarly.

CRAIG ROBINSON: (00:11:43 – 00:11:44) It happens.

JON STEWART: (00:11:45 – 00:12:04) I will tell you this. I can remember as an 18-year-old doing the landscaping at the apartment because I worked for a landscaper in the summer, doing the landscaping at the apartment building that my father lived in with his new family that we had not been told about.

CRAIG ROBINSON: (00:12:04 – 00:12:04) Damn.

JON STEWART: (00:12:05 – 00:12:07) That’s how complicated. That’s how complex it can get.

MICHELLE OBAMA: (00:12:08 – 00:12:20) Yeah. And I hate to say, yeah, I know a few people who are in that, but when you grow up in the world, folks do some stuff. That’s right. But I bet you were pissed.

JON STEWART: (00:12:21 – 00:12:27) Oh, if you think I did a good job on the last day, believe me, there were some divots.

MICHELLE OBAMA: (00:12:27 – 00:12:28) Yes.

JON STEWART: (00:12:34 – 00:12:40) I think to a large extent, I did not clock any of the damage until much later.

MICHELLE OBAMA: (00:12:41 – 00:12:42) The damage to yourself?

JON STEWART: (00:12:43 – 00:12:56) Yeah. To your psyche or to your soul or to any of those things. You don’t really reckon with it until much later. And I was relatively oblivious to a lot of it.

MICHELLE OBAMA: (00:12:57 – 00:13:37) We also come from a generation where nobody talks about anything. Nobody. Kids are just, you know, like they don’t— there was a generation where you thought kids were just, they weren’t taking in anything. And that if you didn’t talk to them about it, it just didn’t bother them.

You know, it’s the same thing. Our parents weren’t worried about what we were doing in life. You know, now you drop your kids off to college, there are college tours, you take them, you unpack them, you take them to lunch. None of us. It’s like, “You go to college and it’s like, how am I going to get there?” You know? And I luckily I had him. So my dad was dropping him off, you know? There’s just no coddling, no conversation.

JON STEWART: (00:13:37 – 00:14:13) Do you wonder— there was always a mindset for me, which was I was going to remedy that. That when I had— because of the feeling ultimately of being estranged from your father, which is, for a kid, it’s a big deal. But once you have kids, it becomes a bigger deal. I think that’s when I really started to reckon with it. Because you go, “Wait a minute. So I love this thing this much, and to just walk away from that and do that.”

MICHELLE OBAMA: (00:14:13 – 00:14:13) Yeah.

JON STEWART: (00:14:14 – 00:14:30) Insanity. But I keep wondering the steps I’ve taken remedially. What am I doing wrong? How much margin of error do I have? Seeking to remedy those wrongs create new wrongs.

MICHELLE OBAMA: (00:14:30 – 00:14:47) Create all new. Yeah, yeah. It’s like we’re, you know, going too far in the extreme. I think that’s something that our generation has to reckon with. And now we’re overparenting in some ways. Right. You know?

JON STEWART: (00:14:48 – 00:15:54) And I also think, and they had this, you know, my dad was a, you know, he was, depressive, and I make no— I’ve come to terms with whatever it was. And I can remember when he was dying, he had dementia. I remember he and I were estranged, and when I knew he was passing, so I went to see him.

And I remember thinking, I felt badly for him. This man who was going through this difficult time and the family that clearly loved him that were going through this time with him. But I did not feel as though that was a part of me in any way. I just felt like, “This poor man, these poor folks. I hope it’s not too bad for them. I hope it’s not too bad for him.” Right. But it was a relationship that— you know, when you talk about bitterness or anger or those things, I didn’t— it was a relationship drained of that through estrangement and apathy.

MICHELLE OBAMA: (00:15:54 – 00:15:54) Yeah.

JON STEWART: (00:15:55 – 00:16:06) And it just— it withered. So by the end there, it— you felt it for the human condition of it, but not for the familial condition of it.

Getting Into Comedy

MICHELLE OBAMA: (00:20:33 – 00:20:34) No.

CRAIG ROBINSON: (00:20:34 – 00:20:38) When did that nugget start?

JON STEWART: (00:20:39 – 00:20:52) It’s a great question. It started right after I was fired from everything else. Where they were like, “You’re unreliable, you can’t do anything,” and glib, which is really—

MICHELLE OBAMA: (00:20:52 – 00:20:53) what were some of those jobs?

JON STEWART: (00:20:53 – 00:21:23) It’s one thing to be unreliable. It’s another thing to be glib on top of it all, man. Joking about your unreliability. I was raised in that same era as you guys where there was no social media, there was no aspiration to influencing. It was never in the ether of this idea that I’m going to, you know, I’ll go into show business or I’ll be— but I knew I wanted to create something.

CRAIG ROBINSON: (00:21:23 – 00:21:24) Okay.

JON STEWART: (00:21:24 – 00:21:48) And I started working in this punk club in Trenton, New Jersey called City Gardens, which was this, you know, warehouse in the middle of Trenton. And all these bands would come through, like Black Flag and, you know, the Ramones and Bad Brains. Just really incredible performers and creative people. And they would be going there only because they were passing between New York and Philly.

MICHELLE OBAMA: (00:21:49 – 00:21:49) Yeah.

JON STEWART: (00:21:50 – 00:21:51) But it opened up this world of possibility.

CRAIG ROBINSON: (00:21:52 – 00:21:52) Okay.

JON STEWART: (00:21:53 – 00:22:02) And one day I just decided, “You know what? I’m going to sell all my stuff. I’m going to get in the car and I’m going to drive to New York and I’m going to live that life.”

MICHELLE OBAMA: (00:22:02 – 00:22:02) Wow.

JON STEWART: (00:22:02 – 00:22:03) And that’s kind of—

MICHELLE OBAMA: (00:22:03 – 00:22:05) How old were you when you were working in Trenton?

JON STEWART: (00:22:06 – 00:22:29) So I was— 20 through 23 or 24 before I decided to move up to New York City. And no one was waiting for me. No one was encouraging me. It’s not like I would tell the guys at the bar, like, “I’m going to be a comic in New York,” and they’d be like, “That makes complete sense.” It was more like, “All right, see you in 6 months.”

CRAIG ROBINSON: (00:22:29 – 00:22:30) So this was right after college then?

JON STEWART: (00:22:31 – 00:22:37) No, right after. I lived and worked in these bars and for the state for a couple of years.

CRAIG ROBINSON: (00:22:37 – 00:22:38) Okay.

JON STEWART: (00:22:38 – 00:22:39) After getting out of school.

MICHELLE OBAMA: (00:22:39 – 00:22:39) Yeah.

JON STEWART: (00:22:39 – 00:22:39) Yeah.

CRAIG ROBINSON: (00:22:39 – 00:22:44) Living with a bunch of friends and trying to, you know, when you were first getting started, like, what was that like?

MICHELLE OBAMA: (00:22:45 – 00:22:46) Like when you were just coming out?

CRAIG ROBINSON: (00:22:46 – 00:22:49) Just coming out. When you left Trenton, you hit the road.

JON STEWART: (00:22:49 – 00:22:51) Brutal. Oh, it was terrible.

CRAIG ROBINSON: (00:22:51 – 00:22:53) Can you talk about that? Sure.

MICHELLE OBAMA: (00:22:53 – 00:22:57) I’d be delighted to talk about how horrible that was.

JON STEWART: (00:22:57 – 00:23:37) Well, like anything else. So unlike things like sports or a lot of other things that you do, there is no doing. But you learn your first time on stage, nobody gives you grace with the idea that like, “Oh, I bet this guy probably sucks because he’s never done it before.”

And I was up in New York for— I ended up getting a job at this Mexican restaurant on MacDougal Street called Panchito’s. And the Bitter End was right up the block on Bleecker. And they used to do— the thing about comedy is you have to work in a club. They have to accept you. It’s called passing you.

CRAIG ROBINSON: (00:23:37 – 00:23:38) Okay?

JON STEWART: (00:23:38 – 00:24:51) So you perform there, and the major clubs, Comic Strip, Catch a Rising Star, Comedy Cellar, have a hierarchy. You can’t just walk in there and be like, “Guys, you’re not going to believe this. I’m here. I know you’ve been waiting.” And part of the structure. So then there were open mics beyond that where you could maybe get some stage time. You’d put, you know, 50 comics would show up, you put your number in a hat and they’d pull them out. So if you had a high number, 48, 47, you’re performing only in front of the 3 other comics that are left because everybody else did their thing and got out.

There’s a place called the Bitter End, more famous probably for music, but Cosby and Carlin and Pryor used to work in those clubs as well. And they would do an open audition night, but after like 4 door’s cover bands, like it was 1:00 in the morning. And so that was my first, 1987, May of 1987. Got up at the Bitter End with my little— had written a whole little thing out. And got up about 30 seconds into it. A guy goes, “You’re terrible.”

MICHELLE OBAMA: (00:24:52 – 00:24:52) Oh.

JON STEWART: (00:24:53 – 00:25:26) And I hit him full barrel. I was like, “No, I’m not.” And then he was like, “That’s it?” And I was like, “What?” And he’s like, “Well, even this is terrible.” And I was like, “Well, according to you, boom.” And so you can imagine everybody’s like, “Is Robin Williams here?” Because this is— no, it was awful. I lasted probably— I didn’t get back on the horse for, like, another 6 months. It was brutal.

MICHELLE OBAMA: (00:25:26 – 00:25:27) Really?

JON STEWART: (00:25:27 – 00:26:17) Oh, yeah. Brutal. But I realized the urge never went away. The desire, the waking up in the middle of the night and writing down stupid thoughts never went away.

And so I just started. What you learn is there’s a process. And so if you immerse yourself in the world, if you get yourself in trouble, the people that are around that process are great guides. They’re not mentors, but they’re guides. They tell you generally what you want to do is you want to hit this, this, this, and this. Good luck. But there isn’t anything to it but to do it. So that’s how you— and I got really fortunate about a year into it. The Comedy Cellar, which is right up the street from the Mexican restaurant that I was the day bartender in. Who’s the day bartender at a Mexican restaurant?

MICHELLE OBAMA: (00:26:17 – 00:26:18) True.

JON STEWART: (00:26:18 – 00:26:21) Now that you pointed out, you just make margarita mix for the night guy to clean up with.

MICHELLE OBAMA: (00:26:22 – 00:26:23) That’s right. But aren’t you happy there?

JON STEWART: (00:26:23 – 00:27:17) Oh, I actually loved it. And so this woman named Esty, who was the booker at the comedy club, and this guy, Bill Grundfest, who was also one of the bookers, they put me on every night. Sunday through Thursday. I wasn’t allowed on the weekends because that was when the good people went. And they made me the last person. So the shows would usually start 8 or 9 o’clock and they’d go to whenever the last person left. So it could be 2 in the morning, could be 3 in the morning.

And that’s how I learned the thing you want to learn as a performer, which is who are you? What do you actually think? What’s your rhythm? What, you know, stop doing an impression of Seinfeld and start doing who you might be. And that’s the ground. You know, that’s how you sort of— and it’s growth.

MICHELLE OBAMA: (00:27:17 – 00:27:22) Who were you when you first started discovering who you wanted to be?

JON STEWART: (00:27:22 – 00:27:22) Yeah.

MICHELLE OBAMA: (00:27:23 – 00:27:24) Who was that, Jon?

JON STEWART: (00:27:24 – 00:28:25) You don’t have the confidence to know if what you’re doing will have any kind of staying power as a skill yet. So you can have a night where you’re just killing it, like, on top of it, and you’re just thinking, like, “I am Robin Williams.” And then the next night, nothing. Same stuff, nothing. And you’re feeling like, “I am the worst person to ever have done that.” And this is the ride you go on those early years.

The win is when you establish a baseline of where you go like, “Oh, I’m starting to develop this at—” like, guys like Jerry, who are such— he’s maybe the best craftsman probably since Carlin, of craft. When you start to feel like there is a craft to it and you’re not going just joke to joke anymore, that’s when you finally develop that confidence a little bit. But it takes a while.

MICHELLE OBAMA: (00:28:25 – 00:28:27) Yeah. How old were you when that happened for you?

JON STEWART: (00:28:28 – 00:28:29) So what time is it now?

MICHELLE OBAMA: (00:28:29 – 00:28:29) Okay.

JON STEWART: (00:28:33 – 00:28:46) I think it was— I don’t think you ever cross a threshold. It’s that you suddenly realize, “I’m not riding this roller coaster as hard as I was.”

MICHELLE OBAMA: (00:28:46 – 00:28:46) Yeah.

JON STEWART: (00:28:47 – 00:29:01) And part of it is comics talk about their development in terms of— the metric is always time. You don’t ever say, like, “I’ve gotten funnier.” You say, “I got 10 minutes.”

MICHELLE OBAMA: (00:29:02 – 00:29:02) Yeah.

JON STEWART: (00:29:02 – 00:29:05) It’s purely a function of time.

MICHELLE OBAMA: (00:29:05 – 00:29:05) Okay.

JON STEWART: (00:29:06 – 00:29:25) Because to make money, you got to have an hour for it. If you can do 15 minutes, you can emcee. That’ll pay you $600 a week. Wow. If you can do 35, you can middle. Now you’re going out there for $900, maybe $1,000 a week. If you can do 45 or 50 and do it in the middle of a check drop.

MICHELLE OBAMA: (00:29:26 – 00:29:28) What do you mean check drop?

JON STEWART: (00:29:28 – 00:29:42) So a check drop is so when you go out to a club and it’s not so much in the city the same, but when you’re working like an improv in another city or Yuk Yuk’s or any of those kinds of things, if you’re the headliner, well, everybody that’s sitting there got to pay at some point.

MICHELLE OBAMA: (00:29:42 – 00:29:43) Yeah. Okay.

JON STEWART: (00:29:43 – 00:29:45) And they’re not going to wait till after the show because they got to turn it over.

CRAIG ROBINSON: (00:29:45 – 00:29:49) Can you keep the attention while the room is turning over.

JON STEWART: (00:29:49 – 00:29:51) In the city, it’s called the check spot.

MICHELLE OBAMA: (00:29:51 – 00:29:51) Yeah.

JON STEWART: (00:29:52 – 00:30:12) So once you get to a point where you have a certain amount of time and you can handle your business during the check spot, that’s when you go, “Wow, okay, now I can— now I can make a living.” And that’s— those are the metrics that you want to hit as you go. And that’s all it was about.

Meeting Tracy

MICHELLE OBAMA: (00:30:12 – 00:30:20) Any girls? Any, you know, were you cute? Were you, you know, I think we all know the answer to that. Oh, no, no.

JON STEWART: (00:30:21 – 00:30:25) I would, you know, I didn’t meet my wife until I was 32 years old.

MICHELLE OBAMA: (00:30:25 – 00:30:29) And you didn’t date before then? You were just hustling? No, no, no, no.

JON STEWART: (00:30:29 – 00:30:31) I had a couple of girlfriends.

MICHELLE OBAMA: (00:30:31 – 00:30:31) See there?

JON STEWART: (00:30:31 – 00:30:37) But the girls that you basically ended up going out with were the waitresses at the comedy club because that’s your whole life.

MICHELLE OBAMA: (00:30:37 – 00:30:37) Yeah.

JON STEWART: (00:30:38 – 00:31:07) Yeah. You know, you don’t, most girls at that time wanted to go do things. And most girls, you’d be like, “So here’s my day. We’re going to get high till 4:00 in the morning, and we’re going to watch a ton of Three Stooges movies. And then I’m going to sleep till around 1:00. Then I’m going to disappear, probably wander around trying to think of some jokes. And I’ll meet you, I guess, around 3:00 in the morning at the Kettle of Fish bar.”

MICHELLE OBAMA: (00:31:07 – 00:31:08) Do it again.

JON STEWART: (00:31:08 – 00:31:20) And we’ll do it again, baby. And a lot of girls, as you can imagine, would be like, “Sign me up.” It is not a lifestyle conducive to the healthiest of those kinds of relationships.

MICHELLE OBAMA: (00:31:20 – 00:31:23) You make a good point. I never thought of it like that.

JON STEWART: (00:31:23 – 00:31:30) Yeah. Even when I first met my wife, she had a regular job. And so she had to be up at 7:00, and I’d roll in 2:30 in the morning.

MICHELLE OBAMA: (00:31:30 – 00:31:33) Hey, honey, I’m home.

CRAIG ROBINSON: (00:31:33 – 00:31:37) And when you met her, at what stage of your career were you?

JON STEWART: (00:31:38 – 00:31:49) Oh, I was in— I was freshly canceled. I was— I met her. I had had a talk show on MTV.

MICHELLE OBAMA: (00:31:49 – 00:31:49) Yeah.

CRAIG ROBINSON: (00:31:50 – 00:31:50) Oh, yeah, right.

JON STEWART: (00:31:51 – 00:31:52) Famously known for its—

MICHELLE OBAMA: (00:31:52 – 00:31:53) We know about it.

JON STEWART: (00:31:53 – 00:32:15) Talk. MTV was this known first for hot talk, and it went real well. And then Arsenio retired, decided he didn’t want to do his show anymore. And Paramount, who owned MTV at the time, got the great idea that what makes more sense than making me the next Arsenio? So I took that time slot. And so you can imagine the confusion.

MICHELLE OBAMA: (00:32:15 – 00:32:16) Didn’t work out.

JON STEWART: (00:32:16 – 00:33:08) That’s exactly right. So— and we knew it wasn’t going to work out pretty quickly. You get the ratings. Yeah.

So I was visiting friends who were filming things in Greenwich Village, and on one of the sets, there was a makeup artist who, when I came in, said, “Do you have a girlfriend?” And I said, “No, of course not.” She said, “Well, I’ve got this girl.” And she describes this girl in ways where I’m like, “This is a lie.” She’s the funniest, sweetest, smartest. You can’t even— she’s the best. So I’m like, “All right, I’ll go out with her.” So she writes the number on a dollar bill. She gives it to me. I go home. I call who turns out to be my wife, Tracy, and we have a long conversation. I mean, like 2 hours on the phone. On the phone.

MICHELLE OBAMA: (00:33:08 – 00:33:08) She—

CRAIG ROBINSON: (00:33:08 – 00:33:09) phone call.

JON STEWART: (00:33:09 – 00:33:10) And the kind of phone, right?

MICHELLE OBAMA: (00:33:10 – 00:33:13) We’re all like, the kind of phone that’s in the wall. It’s called a telephone.

JON STEWART: (00:33:13 – 00:33:14) The kind that had a cord on it.

MICHELLE OBAMA: (00:33:14 – 00:33:15) That’s right.

JON STEWART: (00:33:15 – 00:33:16) You could wander around.

MICHELLE OBAMA: (00:33:16 – 00:33:16) That’s right.

JON STEWART: (00:33:18 – 00:33:42) And she’s lovely, funny, smart. We’re raised in sort of the same area. And I’m like, we, you know, “I’d love to take you out some night. You know, I’ll call you on Friday and I’ll take you out.” Well, at the time I was a pretty heavy smoker and cigarettes cost money, and some of the money that the cigarettes cost are the ones that I had written her number on.

MICHELLE OBAMA: (00:33:42 – 00:33:45) Oh, John.

CRAIG ROBINSON: (00:33:45 – 00:33:46) Okay, okay.

JON STEWART: (00:33:46 – 00:33:50) So I did not call her when I said I was going to call her.

CRAIG ROBINSON: (00:33:50 – 00:33:53) That’s that. I get it. But the story has a happy ending. Relax.

MICHELLE OBAMA: (00:33:53 – 00:33:56) I know, but that just hurts. I mean, it just like, ouch.

JON STEWART: (00:33:57 – 00:34:29) So that was our original thought. So what I ended up having to do was go back to that movie set because I knew they were roommates. So when I found their call sheets, I saw her— the number of the makeup artist. So I knew that was the number. So I was able to call. But it took a lot longer. So when I called her again, it was a lot of like, “Hey, what’s up?” So it took a little while to get back in. Yeah. Yeah.

MICHELLE OBAMA: (00:38:34 – 00:38:35) So how was the first date?

JON STEWART: (00:38:36 – 00:38:49) Fabulous. She— when I’m nervous, I talk too much, and when she’s nervous, she doesn’t talk at all. So we went to a, a little restaurant on 6th Avenue, called Lupita’s East LA Kitchen.

CRAIG ROBINSON: (00:38:50 – 00:38:51) Mm-hmm.

JON STEWART: (00:38:51 – 00:38:53) Or no, Lupe’s. Lupe’s East LA Kitchen.

MICHELLE OBAMA: (00:38:54 – 00:38:55) We don’t know the difference.

JON STEWART: (00:38:55 – 00:38:57) And I could make up anything.

MICHELLE OBAMA: (00:38:58 – 00:38:58) You could.

JON STEWART: (00:38:58 – 00:39:21) We went to Le Cirque. I said, “This woman deserves the most expensive meal. We stopped first at Tiffany’s.” No, I figured first date, quesadilla. And so I sat. And I ate my delicious burrito and her delicious burrito.

MICHELLE OBAMA: (00:39:22 – 00:39:22) Oh no.

JON STEWART: (00:39:22 – 00:39:25) And all the drinks and talked and thought, “This woman cannot stand me.”

MICHELLE OBAMA: (00:39:26 – 00:39:26) Oh no.

JON STEWART: (00:39:27 – 00:39:36) And we’re walking home and I thought, “We’re going by this one bar that I liked. Do you mind if we just stop in there, have a drink?” 2 scotches in, she comes alive.

MICHELLE OBAMA: (00:39:36 – 00:39:37) Jesus.

JON STEWART: (00:39:38 – 00:39:39) 2 scotches in, she just went, “Hi, John.”

MICHELLE OBAMA: (00:39:40 – 00:39:41) She blossomed.

JON STEWART: (00:39:41 – 00:39:44) And, and I was, I was smitten. That was it.

MICHELLE OBAMA: (00:39:44 – 00:39:46) Wow. How long did you guys date?

JON STEWART: (00:39:49 – 00:40:08) How long was it? She knows the answer to this. I believe she said it was too long. She said, “You dated— we dated too long.” I asked her to marry me probably 3 and a half years in. So we’ve been going out for 3 and a half years. We lived together for a couple of years and had all the dogs and all those things.

MICHELLE OBAMA: (00:40:08 – 00:40:08) Oh, yeah.

JON STEWART: (00:40:08 – 00:40:12) How long did you guys know? How long did you know? Did you know with your—

CRAIG ROBINSON: (00:40:12 – 00:40:13) which one?

JON STEWART: (00:40:15 – 00:40:16) The one that stuck.

CRAIG ROBINSON: (00:40:20 – 00:40:53) No, I didn’t know right away because I was going through a major divorce. Oh, and we don’t— we don’t have enough time for me to tell my favorite story of meeting my wife, so I’ll save that one for you. But when I met her, because I was going through this horrible divorce, and I moved back into my apartment, our family’s apartment that we lived in growing up. And my parents had moved. My mom had moved downstairs where my aunt lived.

MICHELLE OBAMA: (00:40:53 – 00:40:55) Short of saying he was living at home with mom.

CRAIG ROBINSON: (00:40:55 – 00:40:56) So I was back at home.

JON STEWART: (00:40:57 – 00:41:00) Your older sister just put you in your place.

MICHELLE OBAMA: (00:41:00 – 00:41:02) It’s like, what are we talking about here? No.

CRAIG ROBINSON: (00:41:03 – 00:41:23) So whenever I would go out anywhere, my mom would be like, “You meet anybody?” And I’m like, “No, Mom, I’m not interested in meeting anybody.” So I met my current wife, Kelly, and didn’t ask for her number or anything. I just met her. And I was like, after my mom asked me that when I came home, I was like, “Maybe I should have gotten her number.”

MICHELLE OBAMA: (00:41:25 – 00:41:28) He’s such a slow burn. Right. He’s always that way.

JON STEWART: (00:41:28 – 00:41:30) I understand that. You’re recovering.

CRAIG ROBINSON: (00:41:30 – 00:41:31) Clueless.

MICHELLE OBAMA: (00:41:31 – 00:41:31) Clueless.

CRAIG ROBINSON: (00:41:34 – 00:41:47) I waited till Thursday because she told me where she worked, and I looked it up and I saw her phone number there. And I— as I’m dialing her number, she sent me an email the exact same time.

JON STEWART: (00:41:48 – 00:41:52) Oh, really? The kismet of— yes, the digital age.

CRAIG ROBINSON: (00:41:52 – 00:41:58) But then we dated for 5 years before we got married. Yeah, yeah, slow burn. It was— it was because—

JON STEWART: (00:41:58 – 00:42:01) did you know how long before he introduced her to you?

MICHELLE OBAMA: (00:42:01 – 00:42:04) I’m bad with time. It was probably within the first year.

CRAIG ROBINSON: (00:42:04 – 00:42:05) It was definitely the first year.

MICHELLE OBAMA: (00:42:05 – 00:42:12) Yeah, it was first year. I mean, whenever he was ready to— did we meet her before the kids met her?

CRAIG ROBINSON: (00:42:13 – 00:42:13) Oh yeah.

MICHELLE OBAMA: (00:42:13 – 00:42:14) Yeah.

JON STEWART: (00:42:14 – 00:42:18) But he probably, you know, did you know that when you met her, did you go like, “Oh yeah, this is, this’ll—”

MICHELLE OBAMA: (00:42:18 – 00:42:27) well, because he was bringing somebody around. I mean, I don’t, my brother is a slow burn. I mean, he’s had like 3 girlfriends his whole life because he was a basketball player.

JON STEWART: (00:42:27 – 00:42:27) Right.

MICHELLE OBAMA: (00:42:27 – 00:42:30) So he was always— yes.

JON STEWART: (00:42:30 – 00:42:41) Basketball players, famously monogamous. You can’t shake a stick and find a basketball player that isn’t dedicated to whatever relationship he has at the moment.

MICHELLE OBAMA: (00:42:41 – 00:42:44) He was also a very monogamous young man.

JON STEWART: (00:42:44 – 00:42:45) Yeah.

MICHELLE OBAMA: (00:42:45 – 00:42:46) So he was very—

JON STEWART: (00:42:46 – 00:42:47) he’s a good man.

MICHELLE OBAMA: (00:42:47 – 00:42:54) He’s a good man. So if he was bringing somebody around, it was like, okay, how are you feeling about the state of our nation?

The State of the Nation

JON STEWART: (00:42:55 – 00:44:13) You know, I’m glad you asked me that. Thank you. I’m going to tell you something, and this is recent, and I don’t know if we’re making news here or not. I’m really beginning to sour on this president. I feel like, you know, you know me. I was with him. You know, then I remember after January 6th, watching the insurrection and watching the police being sprayed with bear spray and being beaten with poles. I remember thinking to myself, “I don’t love this. I’m thinking of maybe not supporting him next time.” But then obviously he won me back.

But no, I mean, I don’t even want to— because I imagine for you and your family and having been that it’s a surreal experience for you guys because of the effort that you put into building something up and to watch it be corrupted, to have this perversion of leadership, I imagine is especially difficult to digest. There’s a surreal quality to it. Although I have to say, you guys left money on the table. A Michelle meme coin.

MICHELLE OBAMA: (00:44:14 – 00:44:20) Didn’t even know it was possible. There were so many things you guys didn’t do a pump and dump.

JON STEWART: (00:44:20 – 00:44:23) It really— you left some money on the table.

MICHELLE OBAMA: (00:44:23 – 00:44:26) We could have had a Netflix deal a decade ago.

JON STEWART: (00:44:27 – 00:45:00) Netflix deal? You could have had a weapons company. You could have sold missiles to yourself. Don and Eric have a drone company. I don’t even know what to say. Yeah, it’s the level of corruption that is in some ways, maybe it’s doing a favor by making this the current power structure and dynamic of this country untenable because of how explicitly corrupt it is. Maybe that’s— I don’t know.

MICHELLE OBAMA: (00:45:01 – 00:46:36) Well, it’s sort of, you know, what do I say? You know what we were saying about the rolling back of women’s rights? I mean, you know, if— when things are okay, now, it’s easier to take what you have for granted and to think, well, there will always be somebody there who wouldn’t possibly do this. We’ve never had somebody who would do this. And you just assume that’s going to be the way it is.

Now, I think at some level we were there as a country, just a little unclear, just a little like, maybe we can get a little more. Maybe I can get more of a tax cut, tax break, you know. I mean, maybe we can get richer than we are, you know, maybe we can get rights changed faster than ever before, right? Because, you know, our kids didn’t witness much of the struggle at all, right? They didn’t experience it. And that’s, you know, that’s the kind of growth you would hope for, for the country, that each generation everything gets better and better and better. And that was actually happening. Right? Until we get to a point where there’s a generation that didn’t even remember what was wrong in the first place. Never saw it, right? I mean, you think about all the young people who only have known— only knew Barack Obama as their president. Like, that was the America. There is that truth too, right?

Life After the White House

JON STEWART: (00:46:37 – 00:47:04) What was the feeling like— because it is a crucible like that. You feel the weight of that house in every room and every piece of furniture that exists in that house. And the responsibility, I imagine, is— it is a weight you bear every day that you walk through there. The day you walk out, is that— is the experience one of liberation? Is it one of exhale?

MICHELLE OBAMA: (00:47:05 – 00:47:07) Are you now interviewing me, Jon Stewart?

JON STEWART: (00:47:08 – 00:47:20) No! No! This isn’t going to make it into the show. I’m just— I would never be interviewing. That’s not what we’re here for. I was just curious.

MICHELLE OBAMA: (00:47:20 – 00:49:04) No, no. I mean, I wrote about this in Becoming. I mean, when we got on that plane after the election and the— the outcome and the disappointment and young people and all of it. I got on that plane and that last trip on Air Force One, and I barely remember much of anything, but the minute I walked through those doors, I burst out in tears. And I think I cried for like 30 minutes straight. And for me, is a show of a release of— it wasn’t sadness. It was, “Thank God we made it to the other side of that experience.” Because it’s not just the responsibility, but as a mother, I was like, “Okay, my kids are whole. My husband is whole.” You know, it didn’t— there was no guarantee that we’d get to this other side in one place. We were proud of what we did, but it was like, it was over. It’s like, phew.

And who would know that? There were 40-some-odd people who’ve ever had that experience. And it’s a weight because it’s not about you. You are responsible for every emotion, every sense of a young person’s being, you know? I mean, everything we were doing, we understood what we were modeling, you know? And it’s like, you don’t want to get it wrong, you know? You don’t want to—

JON STEWART: (00:49:04 – 00:49:22) So you were cognizant of the effects your policies might have on the lives of others. That’s so interesting. So you’re saying is in the middle of, let’s say, a war, you wouldn’t necessarily bring out, I don’t know, the specs for a ballroom.

CRAIG ROBINSON: (00:49:25 – 00:49:43) Jon, let me tell you, as their brother, or her brother, and brother-in-law, and all Black people, we were— it feels like I was holding my breath for 8 years.

JON STEWART: (00:49:43 – 00:49:43) Really?

CRAIG ROBINSON: (00:49:44 – 00:50:03) Because of the magnitude of what they had in front of them and how if they had somehow accidentally or maliciously done the wrong thing, how it would’ve affected the entire race.

JON STEWART: (00:50:04 – 00:50:04) Right.

MICHELLE OBAMA: (00:50:05 – 00:50:06) That’s—

CRAIG ROBINSON: (00:50:06 – 00:50:07) people don’t talk about that.

JON STEWART: (00:50:07 – 00:50:07) Right.

CRAIG ROBINSON: (00:50:08 – 00:50:08) And, you know—

JON STEWART: (00:50:08 – 00:50:10) It’s the Jackie Robinson of it.

CRAIG ROBINSON: (00:50:10 – 00:50:12) It’s the— it’s like, well, that’s it for—

MICHELLE OBAMA: (00:50:12 – 00:50:12) That’s it.

CRAIG ROBINSON: (00:50:12 – 00:50:13) That was your turn. That’s it.

JON STEWART: (00:50:13 – 00:50:14) All right, let’s try a Jew.

CRAIG ROBINSON: (00:50:17 – 00:50:28) But, but it’s, you know, so, not that you asked me, but I was relieved on that at the end. Really?

JON STEWART: (00:50:28 – 00:50:37) Oh, that’s an interesting part of it too, is to be the family but to not be in the house.

CRAIG ROBINSON: (00:50:38 – 00:50:38) Yes.

JON STEWART: (00:50:39 – 00:50:48) Also because you’re not ensconced in it, you’re on the outside feeling all of the outside noise. I imagine the house can somehow function as a bit of a—

CRAIG ROBINSON: (00:50:48 – 00:50:48) They’re bubbled up.

JON STEWART: (00:50:49 – 00:50:49) Right, right, right.

CRAIG ROBINSON: (00:50:49 – 00:50:54) They’re bubbled up. But I’m out in the streets like a civilian, and I’m dealing with all that.

JON STEWART: (00:50:54 – 00:51:04) Now, as the brother, was it hard to hold your powder when— because I know, listen, noise is noise, and everybody hears it. So I would imagine—

CRAIG ROBINSON: (00:51:04 – 00:51:07) You know, I think at the time, I was still coaching.

JON STEWART: (00:51:08 – 00:51:08) Right.

CRAIG ROBINSON: (00:51:11 – 00:51:29) What I always said to people was that as long as I know they’re in there, I know they’re trying to do the best for the most people. So what the noise I was hearing wasn’t that bad. And plus people were telling me I couldn’t coach and needed to be fired anyway.

JON STEWART: (00:51:30 – 00:51:32) So you had your own noise you were dealing with. I had to deal with that.

CRAIG ROBINSON: (00:51:32 – 00:51:42) No, no. But it, I had the utmost confidence in him, so I wasn’t worried about the noise because it didn’t mean anything.

JON STEWART: (00:51:42 – 00:51:47) Right.

Comedy, Power, and Politics

MICHELLE OBAMA: (00:55:20 – 00:55:36) Did you know you would be doing what you’re doing with comedy at this level? I mean, was there always a political curiosity, a passion, you know, and finding a way to incorporate it into your comedy?

JON STEWART: (00:55:36 – 00:56:27) Well, yeah. So that’s, you know, we talked earlier a little bit about like your first 15 or 20 minutes is almost always biographical. And then you move into kind of observational. And observational can be the sort of behavioral, from the minutia to the trivial to something more consequential about relationships or things like that. But I was never particularly interested in those dynamics. I was interested in power dynamics. I was interested in the way that the world functioned and had always been that way. In school and everything else. And so that was— I think if you wanted to feel like you were being authentic, you try and write material that reflected your passions and interests. And that’s sort of where that all came from.

CRAIG ROBINSON: (00:56:28 – 00:56:31) Yeah. And then how did the whole Daily Show come about?

JON STEWART: (00:56:33 – 00:58:40) So the Daily Show came about. Doug Herzog and Madeleine Smithberg and Lizz Winstead were these 2 producers and then the head of, at the time, Comedy Central. Doug had wanted to do kind of, what’s the Comedy Central answer to SportsCenter? What would make this network feel like it was a sort of living entity? And so The Daily Show is what Madeleine and Lizz produced to that end.

And they had a host, a basketball player, Craig Kilborn. And he had decided to go off to do Network. And I’d been out of work for a while. I’d written a book and done some other stuff and kicked around the clubs and done some incredibly memorable independent film roles. And yeah, that wasn’t happening. And they asked me if I wanted to do it. And I had said, “You know, let me think about it.” And I thought about the way that I saw that the show was and the way that I wanted to make it. And so we had discussions about— I thought that it could be a vehicle to explore those themes of power and politics and the distance between— I was always really interested in the room before the room, the room where the meeting took place. And then the politicians would go out and they would give their speech. And you always wonder, “Okay, every—” because as you know, like, everything’s purposeful, everything is intentional. So how are they designing that? And it used to be sometimes. Now you just have a guy wake up at 3 in the morning and go, “I think I might be Jesus.” Point is this. But that’s what I wanted the show to be, to deconstruct what we see as power’s reality. What’s the reality behind that? And that seemed like the right forum for it. And also, surrounded by just great writers and performers, and the list of them is endless.

CRAIG ROBINSON: (00:58:40 – 00:58:42) Speaking of, we had Jessica Williams on.

MICHELLE OBAMA: (00:58:43 – 00:58:45) Oh, God. She is amazing.

CRAIG ROBINSON: (00:58:46 – 00:58:46) She’s amazing.

JON STEWART: (00:58:46 – 00:58:47) She’s the best.

CRAIG ROBINSON: (00:58:47 – 00:58:52) Raved about your mentorship, and you should be very proud.

JON STEWART: (00:58:54 – 00:59:31) Listen, it’s like you don’t want to screw that. Like, she is such a rare— I watch videotapes all day looking for talent, and you watch them with sort of that idea. It’s like scrolling on before Instagram. You’re just doing this, going through, and then every now and again, you go, “Huh? That’s Jessica.” She— and I mean, like, not a produced, like, some low-rent old Sony Handycam, like, nothing video. And she just explodes off it.

MICHELLE OBAMA: (00:59:31 – 00:59:31) Yeah.

JON STEWART: (00:59:31 – 00:59:47) And is— and what a lovely person. And but a talent that— I mean, she’s obviously doing— but we knew that the minute you saw her. And she was, I think, 20 years old, 21. Like, it was crazy. We couldn’t even believe that.

MICHELLE OBAMA: (00:59:48 – 00:59:49) And she had never done it before.

JON STEWART: (00:59:49 – 01:00:20) Never done it. Came in and was just— certain people vibrate with no delay, like an electrical. She has like an electrical. So the synapse is just fire. And she’s that as a talent. And the best thing that I tried to do was try and find the most talented people I could and let them be them. I’d love to say that it was like my guidance of that. Like I was—

MICHELLE OBAMA: (01:00:20 – 01:00:26) Well, you wouldn’t say that, but a lot of other people have said that about you. I mean—

JON STEWART: (01:00:26 – 01:00:26) Well, that’s very—

MICHELLE OBAMA: (01:00:26 – 01:01:10) that’s kind of— you know, they have talked about you being the leader at that table. I mean, you know, the table that they were surrounded by, there was still— your work ethic, there was still the example of your— and I’m using the words that I’ve heard too. You know, it was still your work ethic. It was still the tone that you set around that table. And you know that there are tables, other comedy tables where, you know, no, it’s just the opposite. It’s a little rough and nobody’s rooting for you. And there isn’t the, you know. So I don’t know whether that’s a question because you won’t take it. And you won’t say, “How did you do that, Jon? How did you feel?”

JON STEWART: (01:01:10 – 01:01:36) But once I read Sun Tzu’s The Art of War, I think I’d been in a lot of places that were not healthy. And when I first got there, I don’t think it was healthy. I think it was rough and quite toxic, and that people’s ambition was— I think it’s hard for people to sometimes understand, and maybe in this show, is that if the show’s good, we all win.

MICHELLE OBAMA: (01:01:37 – 01:01:37) Yeah.

JON STEWART: (01:01:37 – 01:01:53) And so if we all— the energy that it takes you to create toxicity or selfishness or to be overly combative is energy that you’re not using to elevate.

MICHELLE OBAMA: (01:01:53 – 01:01:56) Listen, America, can you say that again?

JON STEWART: (01:01:58 – 01:02:36) El partido de fútbol. ¿Dónde vas cantando a pleno? It was, you know, there’s only a finite amount of energy in the day. So I had to learn how to parcel that energy for myself, but also for the staff to understand that, like, we’re— it’s in some respects, it’s a refinery, and we’re taking raw materials in the morning, and we’re trying to create a process that can refine those materials into something that we feel is— and I don’t want to say great, not great thing, but the greatest execution of our aspiration or intention.

MICHELLE OBAMA: (01:02:36 – 01:02:36) Yeah.

JON STEWART: (01:02:36 – 01:03:33) Every day has to set an intention. And that’s why for me, it’s almost more fun to work on the process because the process was so crucial in creating the product. And that was what— that was the gift of having people around me who also really sort of dug that idea. Like, “Let’s sit and talk about—” because 5 minutes at 9:00 AM is 45 minutes at 6:00, but now there’s an audience waiting there. So if we can figure out how to create a process that’s repeatable but not stifling, that was like— it was this great dynamic of challenges. Yeah. And what I loved about it, I felt like it was the first time it used every part of anything that I thought I was able to do to its totality.

MICHELLE OBAMA: (01:03:33 – 01:03:33) Yeah.

JON STEWART: (01:03:34 – 01:03:54) And that’s why it was so nice to be able to come home to my family completely drained and spent so that I had nothing left for them. I think the answer here is this. Work hard, deplete yourself, have nothing left for others, for your family.

Family Life and Parenting

MICHELLE OBAMA: (01:03:55 – 01:04:08) Well, what was family life like for you before you realized that you were— I mean, was Tracy patient with it? Was she getting a little pissed off about it? Did she understand?

JON STEWART: (01:04:11 – 01:04:16) I think that it’s hard whenever you have young children.

CRAIG ROBINSON: (01:04:19 – 01:04:19) Yes.

JON STEWART: (01:04:20 – 01:04:22) And this is probably for just me and Craig.

MICHELLE OBAMA: (01:04:24 – 01:04:24) Dumb boys.

JON STEWART: (01:04:24 – 01:04:38) Dumb boys. Is when you walk into the house, when there are 2 young children there and you’ve been working all day, the first thing you might not want to say is how tired you are.

CRAIG ROBINSON: (01:04:38 – 01:04:42) Yes. Yes. You can’t do that. It’s a no-no.

MICHELLE OBAMA: (01:04:42 – 01:04:46) Yeah. And we should put that on a t-shirt.

JON STEWART: (01:04:47 – 01:04:47) Don’t say how tired you are.

MICHELLE OBAMA: (01:04:48 – 01:04:50) Don’t. Don’t do it.

JON STEWART: (01:04:51 – 01:05:22) But she’s also like, she’s just a rare bird. Like, incredibly supportive. But it took me a while to understand and really understand it. How hard it was for her in those years. It was really hard. Yeah. And the person that’s coming into that, that you’ve been Wisconsin-ing the whole day, also can come into it as the amusement park.

MICHELLE OBAMA: (01:05:22 – 01:05:22) Oh, God. Yeah.

JON STEWART: (01:05:22 – 01:05:39) So you can walk in. It’s been a long day of tears and limits and trying to set— raise them to be responsible things. And then this one comes in, it’s like, “Who wants to ride on my back?” And you’re a wrecking ball.

MICHELLE OBAMA: (01:05:39 – 01:05:40) That’s right.

JON STEWART: (01:05:40 – 01:05:45) In this entire operation. And you think it’s, “But I don’t get any time with them and I do this.”

MICHELLE OBAMA: (01:05:45 – 01:05:46) Yeah.

JON STEWART: (01:05:46 – 01:06:37) And so dealing with all that, it can be really fraught. But what’s so interesting is as they become autonomous— and obviously those old ways of raising them when they’re little, that it’s nice to be important, but it’s more important to be nice. But as they get older, you’re like, you know, “They put fentanyl in Coke, right? Just be aware.” But then it’s just the two of you again. And it’s a really kind of lovely— like, it’s a comfort. Like, you’ve been through all these wars, and now you’re kind of just together again on the couch. And you obviously miss— the energy and excitement of the kids being around is so incredible.

MICHELLE OBAMA: (01:06:37 – 01:06:38) I don’t miss them.

CRAIG ROBINSON: (01:06:38 – 01:06:38) I don’t.

MICHELLE OBAMA: (01:06:38 – 01:06:56) I love them. I’m going to see them tonight for dinner. I love them. But Barack cried when they went to college. I was like, “Bye, little— goodbye.” Now I— now Friday nights aren’t wrecked with terror and fear about, “Where are you? Where are you?”

JON STEWART: (01:06:57 – 01:06:57) Right.

MICHELLE OBAMA: (01:06:58 – 01:07:01) You know, I love their emancipation and growth.

JON STEWART: (01:07:01 – 01:07:07) And the thing I miss though is the job. Like, don’t you miss— see, your kids are still in high school, so it’s still a job.

CRAIG ROBINSON: (01:07:07 – 01:07:07) Yes.

JON STEWART: (01:07:08 – 01:07:12) Like, the— it gave a meaning and like pattern to my life.

MICHELLE OBAMA: (01:07:12 – 01:07:13) I’m good.

CRAIG ROBINSON: (01:07:13 – 01:07:15) Yeah, she’s different.

MICHELLE OBAMA: (01:07:15 – 01:07:16) She’s different.

CRAIG ROBINSON: (01:07:16 – 01:07:22) I have a wonderful pattern. Oh man, you know, I love my kids’ schedule.

JON STEWART: (01:07:22 – 01:07:23) I love it. Yeah, there’s something about the schedule.

CRAIG ROBINSON: (01:07:23 – 01:07:24) I love their schedule.

MICHELLE OBAMA: (01:07:24 – 01:07:40) I love my schedule. I have a great schedule and it’s all mine. But I think fathers can be that way because you weren’t there from 6 and 9. You missed a lot of it. I mean, I’ve had so much quality time with my children.

JON STEWART: (01:07:40 – 01:07:41) That’s so funny.

MICHELLE OBAMA: (01:07:41 – 01:07:45) So much. Yeah, yeah. I know them inside and out.

JON STEWART: (01:07:45 – 01:08:04) Oh, and it must drive you crazy. I’m sure it must have driven my wife crazy when, when I first left the show. And so it was all about then driving the kids to school and driving them home. And I’d come back with them, they were in the car and they were talking about this, they were laughing. And, you know, it never occurred to me, but I’m sure my wife was thinking about how lovely.

MICHELLE OBAMA: (01:08:04 – 01:08:06) Yeah, yeah, you just soak it all in.

JON STEWART: (01:08:06 – 01:08:52) But we, at that time too, we moved out of the city. So we went through a kind of a strange— I don’t know if you guys have ever experienced this, but so when we were in the city, we went— they went to school in Greenwich Village called a little school called Little Red, literally like the school Pete Seeger went to. Yeah, every assembly ends with, you know, “Hammer, and it’s the hammer of justice,” feed all the children, and we all hold hands and somehow just levitate. You know, it’s all just magical.

And we moved them out to Jersey, and this was 2015. I remember dropping them off at school, and the first bumper sticker I saw was “Hillary for Prison.” And I was like, “Oh, okay.” I don’t think “if I had a hammer” is how this thing is going to go. But that was a big adjustment.

MICHELLE OBAMA: (01:08:52 – 01:08:52) And they—

JON STEWART: (01:08:55 – 01:09:05) in some ways, I’m really glad that that happened because we were ensconced in something that was really eccentric and kind of cloistered.

Comedy’s Role in Politics Today

MICHELLE OBAMA: (01:09:05 – 01:09:11) Yeah. Do you think comedy helps or hurts the political climate.

CRAIG ROBINSON: (01:09:11 – 01:09:11) Oh, wow.

MICHELLE OBAMA: (01:09:12 – 01:09:29) Because here’s what, you know, I mean, sometimes I just can’t watch anything political. Sure, sure. Right. Especially then, because it was like, sure, is this, is this funny?

JON STEWART: (01:09:30 – 01:09:30) Right, right.

MICHELLE OBAMA: (01:09:30 – 01:09:47) You know, it’s personal. Is it? Yeah, yeah, yeah. But I, you know, I wonder what you think, because sometimes I think, is it good that most young people are getting their news from The Daily Show?

JON STEWART: (01:09:47 – 01:09:47) Right.

MICHELLE OBAMA: (01:09:49 – 01:10:01) Or that they, you know, they want you to run for president? Or, you know, I mean, that we’re in that position of where, you know, especially with social media.

JON STEWART: (01:10:01 – 01:10:01) Right.

MICHELLE OBAMA: (01:10:01 – 01:10:02) It’s like the funny guy—

JON STEWART: (01:10:02 – 01:10:27) I think social media has— look, I think the shows that we do now, they go out on social media on the thing. But to a large extent, because we are infrastructure heavy, we are in some ways a relic of a previous era where it’s sort of like I’m running a Blockbuster, a video store inside of a Tower Records. You know what I mean? Like, it is where people will just be like, “So you sell what now?”

MICHELLE OBAMA: (01:10:28 – 01:10:28) CDs?

JON STEWART: (01:10:28 – 01:10:39) Right. But in other ways, it has more reach because social media places it everywhere. The question is, what does— I never confuse cultural power with power.

MICHELLE OBAMA: (01:10:39 – 01:10:39) Yeah.

JON STEWART: (01:10:41 – 01:12:20) I learned early on that one of the frustrations of— one of the joys of it is catharsis and being able to express yourself and do that thing that we talked about. Like, what do you want to be as a comic? I want my personal thoughts and dreams and whatever to be filtered through whatever art form it is that I’m pushing through. Second item of it is, but it’s impotent. And is it an opiate? Is it creating— and having worked on some of those things on Capitol Hill and all that, I know the difference now, which I didn’t before. The difference between activists who are in the trenches doing that day-to-day work, trying to bend that arc of the moral universe slowly towards justice, not realizing there’s a bunch of people trying to bend it back.

And so I wish there were metrics. I wish there was a double-blind study where you could find out, like, “Am I hurt? Does this help? Does it corrode? Does it pervert?” Is it something to be— is it ultra-processed food that’s given the country a kind of political diabetes? I don’t know. I think I also have to step back on— it may not be an honorable thing we do, but we do it as honorably as we can in that it is not in bad faith. So the way that I try and judge it is any good faith art, material, speech, talk that goes into the universe, I feel like is a win. There’s so much bad faith.

MICHELLE OBAMA: (01:12:20 – 01:12:20) Yeah.

JON STEWART: (01:12:21 – 01:12:35) And I try to hold that, but I can’t sit here and honestly answer like, “It’s a win for society.” Like what I’ve done over these past 25— you know, I don’t, I’d hate to think, obviously.

MICHELLE OBAMA: (01:12:35 – 01:12:36) Yeah, yeah.

JON STEWART: (01:12:37 – 01:12:43) But there’s many people on social media who would tell me, you know, that that is the case.

MICHELLE OBAMA: (01:12:43 – 01:12:43) Yeah.

JON STEWART: (01:12:44 – 01:12:59) And the other side of it is, you have to be agnostic about— you don’t get close to the people. Like, the relationships with political figures are always fraught, or with media figures. I always just say to people at the show, “Look at the people around you.”

MICHELLE OBAMA: (01:12:59 – 01:12:59) Yeah.

JON STEWART: (01:13:00 – 01:13:04) When you leave here, if we do this right, these will be your only friends.

MICHELLE OBAMA: (01:13:04 – 01:13:05) Right, right.

JON STEWART: (01:13:05 – 01:13:21) Because one of the things about the sort of media industrial complex and the political media industrial complex is the associations diminish the purpose of what some of those disciplines are. They can exist in that. And so that’s hard.

MICHELLE OBAMA: (01:13:22 – 01:13:22) Yeah.

JON STEWART: (01:13:22 – 01:13:38) You know, because you do feel there are people you really like, you really admire, but you know at work, like, you’re going to have to— and I’m sure for you guys, there’s people you might like who do those things and you go, “I think I’d like to punch that guy in the face.” You know, that kind of thing.

MICHELLE OBAMA: (01:13:39 – 01:14:31) Well, and to answer my own question of you, I do think the cultural impact is important. I mean, I’ve always thought that, that power is— it’s not the same, but it’s really important. I mean, I felt that way even when I was First Lady, and I think our administration understood that there was the Washington power, but it’s like if you wanted to talk to anybody, if you wanted anybody to hear you, really, you needed to go at it from the culture. Right, right. Where people are. Right. And not try to buck it. I mean, I didn’t do one interview with Face the Nation or Meet the Press. Right. Right. I never sat down with the New York Times editorial board.

JON STEWART: (01:14:31 – 01:14:31) Right.

MICHELLE OBAMA: (01:14:31 – 01:14:33) But I came on The Daily Show.

JON STEWART: (01:14:33 – 01:14:35) Right. And you never tried to have us arrested.

MICHELLE OBAMA: (01:14:35 – 01:14:38) Oh, I didn’t. I didn’t. Although if I knew, I could have.

JON STEWART: (01:14:38 – 01:15:24) Or taken off the air. Or no, but it’s a function of— it’s a function of a confidence in your worldview. There is nothing more, I think, fragile than someone who wields real power, who feels that that power will be diminished by satire or commentary. It’s kind of a shocking fragility for someone who wants to project alpha male dominance and yet be so incredibly wrecked by something that happens at 12:30 at night. I mean, he’s made all of our shows relevant again in a weird way.

Closing

MICHELLE OBAMA: (01:15:28 – 01:15:30) Well, I thank you.

JON STEWART: (01:15:31 – 01:15:38) Listen, I thank you guys for coming over. It’s been such a delight. Now, you know, I turn this room— my book club is going to be here.

MICHELLE OBAMA: (01:15:38 – 01:15:42) It’s true. Are you enjoying the podcast? The podcast space?

JON STEWART: (01:15:42 – 01:15:43) Oh, the one that we do?

MICHELLE OBAMA: (01:15:43 – 01:15:48) Yeah. The one where you should be interviewing people and not—

JON STEWART: (01:15:48 – 01:15:52) I get to talk to all kinds of different people, and I get to do it in my house, which is just—

CRAIG ROBINSON: (01:15:53 – 01:15:54) that’s perfect. Yeah.

MICHELLE OBAMA: (01:15:54 – 01:15:55) That’s so cool.

JON STEWART: (01:15:55 – 01:16:02) And it’s also a way, you know, as you guys, we talked about a little earlier, I am not the most socially inclined individual.

MICHELLE OBAMA: (01:16:02 – 01:16:06) Yeah, that was the most surprising thing when I met you.

JON STEWART: (01:16:06 – 01:16:07) Oh, really?

MICHELLE OBAMA: (01:16:07 – 01:16:09) Oh, yeah. I mean, oh, he’s so shy.

JON STEWART: (01:16:09 – 01:16:10) Yeah, yeah, no, I’m—

MICHELLE OBAMA: (01:16:10 – 01:16:12) And he’s extremely anxious about the world.

JON STEWART: (01:16:12 – 01:16:13) Yes, that is correct.

MICHELLE OBAMA: (01:16:14 – 01:16:18) But is it true that you keep your Emmys in a box? In a—

JON STEWART: (01:16:18 – 01:16:20) Yes, I’m sure.

MICHELLE OBAMA: (01:16:20 – 01:16:21) In a—

JON STEWART: (01:16:21 – 01:16:36) Yeah. I’ve never been— attached to material or awards or any of those sorts of things. I’ve always— my wife found me when she found me. I lived out of those milk crates that you used to get with all this stuff.

MICHELLE OBAMA: (01:16:36 – 01:16:38) And I’m barely out of those.

JON STEWART: (01:16:38 – 01:16:45) Barely out of that. But no, it’s lovely to talk to you guys, truly.

Listener Question: Staying Sane in a Chaotic Political Climate

CRAIG ROBINSON: (01:16:45 – 01:16:50) Well, you know, we have a listener question that we need to answer that will—

JON STEWART: (01:16:50 – 01:17:00) Sagittarius. You’re fire, girl. I don’t know where that is. I don’t know what camera I’m looking at. I’m in surround sound over here.

MICHELLE OBAMA: (01:17:00 – 01:17:52) All right. All right. Who’s our listener question from? All right. So this is from Eric. “Hi, Michelle and Craig. My dilemma is this. I am certain that fixating on politics and political conversations right now will not improve the negativity, divisiveness, and hopelessness that I have and that seems to be everywhere. At the same time, it can feel naive to ignore things altogether because so many things ail the world right now. The economy, loss of rights, deaths at home and in wars overseas, the environment. So where does that leave the average person like me who both wants to escape or at least ignore the nightmare of our current political landscape, yet also understands that doing nothing won’t actually improve anything? What is the kind of work we can be doing and what are the conversations we should be having that might make a difference, but also allow us to keep our sanity?” From Eric in Vermont.

JON STEWART: (01:17:53 – 01:18:07) Okay, Eric, your listeners are deep. We do something like this on my show and it’s always like, “What’s your Taco Bell order? Are you a chalupa guy?” Eric’s going through it, man.

MICHELLE OBAMA: (01:18:07 – 01:18:09) Yeah, yeah, he’s— I don’t think he’s—

JON STEWART: (01:18:09 – 01:18:10) oh wait, are you looking at me to answer this?

MICHELLE OBAMA: (01:18:10 – 01:18:12) Oh yeah, yeah, yeah, that’s right.

JON STEWART: (01:18:12 – 01:18:18) I turned to answer like this, like, you’re the answer. Let’s see what you got.

MICHELLE OBAMA: (01:18:18 – 01:18:24) We’ll all jump in, but we want to be polite and let our guests go first.

JON STEWART: (01:18:25 – 01:19:40) Action is the antidote to anxiety. And I’ve always felt that existential anxiety is something you can never get your hands around. But what you can get around are tactile. It’s so funny that this is coming up. So I’d had this conversation with Trevor Noah about anxiety, and that’s why I like woodworking. I’ve learned how to play the drums. They’re things that are mechanical, they’re tactile, they are rhythmic, they are repeatable, and they are grounding for me mentally. And he just sent me this. Apparently Winston Churchill felt the same way. He sent me this thing about Winston Churchill used to be visited by depression. I don’t have that, but he’d be visited by depression and he would call it the black dog. And when the black dog would visit, he had to do things with his hands. He had to make things. He had to— And so, Trevor was just sending me that, you know, “This is your coping mechanism put to explicit eloquence by Winston Churchill.” And then I just wrote him back and said, “That’s so crazy. It explains why I always feel like I want to bomb the Germans.”

CRAIG ROBINSON: (01:19:42 – 01:19:42) And, uh—

JON STEWART: (01:19:42 – 01:20:09) But I would think, you know, young people feel this way. In the olden days, you got rid of that with booze. That’s kind of how people dealt with that existential anxiety because they couldn’t talk it out. But I don’t know, anybody that I think that is able to articulate it in that way can get through it because naming it is one of the hardest things.

MICHELLE OBAMA: (01:20:09 – 01:21:10) Yeah. I mean, one thing I totally agree— because some of you, you just got to work through it. And I totally agree with the tactile piece. I knit, I knitted my way through COVID. I play tennis like 3 times a week. And the repetition of the thing, because you’re on there, it’s like, “I have to run and hit that ball.” I can’t think about anything else while I’m doing it. And I’m trying to figure out how to hit the ball better. And I can do that for 90 minutes. And it, you know, that’s 90 minutes of not thinking about anything except for that thing. So I completely agree with that.

The other thing I often say to people is, yeah, I think we run into the challenge of thinking that all change has to be big change. I think young people think that too. You know, when you hear about the young people doing something, well, “I got 1,000 people to vote, or I raised this.” I mean, it’s just like they’re often biting off so much.

JON STEWART: (01:21:10 – 01:21:10) Yes.

MICHELLE OBAMA: (01:21:11 – 01:21:32) You know, “How do I end drug dealing in my neighborhood? How do I fix this huge, gigantic problem right under my nose?” And the answer is you can’t. You know, what you need to do first of all is just focus on what you can control. You know, focus on small right now, especially young people.

JON STEWART: (01:21:32 – 01:21:32) Right in front of you.

MICHELLE OBAMA: (01:21:32 – 01:21:33) It’s like right here.

JON STEWART: (01:21:33 – 01:21:33) Right.

MICHELLE OBAMA: (01:21:34 – 01:21:37) You know, it’s like, are you in school? Stay in school.

CRAIG ROBINSON: (01:21:37 – 01:21:37) Right.

MICHELLE OBAMA: (01:21:38 – 01:21:43) Do your homework. You know, that’s, that’s, you know, that’s some power right there.

JON STEWART: (01:21:43 – 01:21:46) Absolutely. And it’s also sort of the quiet activism of living pleasantly.

CRAIG ROBINSON: (01:21:47 – 01:21:47) Yes.

JON STEWART: (01:21:47 – 01:22:05) Like in the sense of everybody that you encounter in your world, whether it’s at a deli nearby or when you go to the thing, if you interact with them in a way that recognizes their shared humanity, I’m telling you, man, that makes—

CRAIG ROBINSON: (01:22:05 – 01:22:05) it works.

MICHELLE OBAMA: (01:22:05 – 01:22:05) It’s kind of huge.

CRAIG ROBINSON: (01:22:05 – 01:22:05) It works.

JON STEWART: (01:22:06 – 01:22:06) And it’s funny.

CRAIG ROBINSON: (01:22:06 – 01:23:04) It’s funny that Eric is in Vermont because that goes to what I was going to say to Eric. You know, I probably never told you this, but when you all were first running, I used to be a surrogate. So I’d have practice during the week, and then on Sundays they’d send me somewhere. Oh, wow. And I’d give the team off, and then we’d practice late on Monday so I’d be able to travel back.

And one of the first places I went was this small town up in Vermont. Really small, right by the water. And I remember there’s a small little general store that I got dropped off at to be picked up by somebody else and be taken somewhere else. And I went in the general store and I’m like in a suit and everybody’s wearing flannel shirts, right? And this guy says to me, “You’re not from around here.” And I was like, “Oh, you figured that out.”

MICHELLE OBAMA: (01:23:06 – 01:23:08) Oh, just the suit, you think?

CRAIG ROBINSON: (01:23:08 – 01:24:13) Yeah. And no, and it’s— I didn’t say because I was Black. I said it’s because I had the suit on. Because he knew why I was there, but he pretended that he didn’t know. And he’s like, “You know, we got a lot of politicians coming up around here. You got anything to do with that?” And I was like, “Yeah, I do. I happen to be coming up here to talk about Barack Obama.” And then I went into this whole thing. He’s like, “Well, I don’t know about that guy.” And I said, “Well, why not?” He said, “Well, he hadn’t done much.” And so I went into this very calm and quiet discussion about why you have to, every now and then, give a chance to people who don’t have the same experience that other people have because they haven’t had the same opportunity. Real basic stuff, but it was quiet and it was calm and it was an hour of it. And by the end of it, he was— I don’t know who he voted for, but he acted as if I had convinced him.

JON STEWART: (01:24:13 – 01:24:14) Right, right.

CRAIG ROBINSON: (01:24:14 – 01:24:28) And I say this to Eric, to Jon’s point, there’s nothing like conversation with people. And to your point, Mish, it doesn’t have to be with 1,000 people. Just hit them one person at a time.

MICHELLE OBAMA: (01:24:30 – 01:24:30) Right.

CRAIG ROBINSON: (01:24:30 – 01:24:43) And talk to them about how you feel and how you think. And if you’re smart and can put a few sentences together, people will listen to you.

JON STEWART: (01:24:44 – 01:24:48) How crazy would it be if that guy Eric is that guy you talked to?

CRAIG ROBINSON: (01:24:48 – 01:24:49) That would be Vermont.

JON STEWART: (01:24:49 – 01:24:56) And it was just like, “Oh, I had this question I wanted to ask him in the store, but I couldn’t do it.” Now I got to wait 16 years. Yeah, I’m going to throw it in there.

CRAIG ROBINSON: (01:24:56 – 01:24:58) Eric sounds younger than the guy.

MICHELLE OBAMA: (01:24:58 – 01:25:05) Yeah, yeah. Well, Eric, hopefully that helps you out a little bit. And anybody else who’s listening, thank you, Jon Stewart.

JON STEWART: (01:25:05 – 01:25:06) Thank you, guys.

MICHELLE OBAMA: (01:25:06 – 01:25:08) You’re a very intelligent young man.

JON STEWART: (01:25:08 – 01:25:13) I heard there was a PA job available. I saw the fruit.

MICHELLE OBAMA: (01:25:13 – 01:25:13) We don’t pay much.

JON STEWART: (01:25:13 – 01:25:33) I just want to point out the difference when you do a podcast with a former First Lady and her brother. The fruit selection in their green room puts basic cable to such shame. I was literally marveling. I was like, “Is that a raspberry?” The exotic nature.

MICHELLE OBAMA: (01:25:34 – 01:25:36) It’s only for the guests. No.

JON STEWART: (01:25:37 – 01:25:39) No, it was so nice to see you again and catch up.

MICHELLE OBAMA: (01:25:39 – 01:25:41) Thank you for spending this time.

CRAIG ROBINSON: (01:25:41 – 01:25:42) It’s been great.

MICHELLE OBAMA: (01:25:42 – 01:25:43) Hopefully we’ll see you again soon.

JON STEWART: (01:25:43 – 01:25:44) Beautiful.

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