Keep Paddling with Conan O’Brien

6:21Craig Robinson:You are my friend, Conan.

6:23Conan O’Brien:I'm a little jealous of Conan because the way you talk about him being such a nice guy and doing things for you, it just sounds like me.

6:32Craig Robinson:Are you jealous? And that's probably why I like Conan. Because he's a tall, friendly guy, just like my big brother. But I think he's probably done a little more for me over the years than you have.

6:47Conan O’Brien:I know. I've been busy. I've been busy. I've been busy. Well, let me give just a couple of flowers here for Conan. As everyone knows, he's a television host, comedian, writer, producer. He hosted three late night talk shows, Late Night with Conan O 'Brien, The Tonight Show, and Conan, and is currently the host of the podcast Conan O 'Brien Needs a Friend. He has one in me. Which I have recently learned was the first podcast that you ever did.

7:25Craig Robinson:Yeah, he was one of the ones I felt safe with in that early stage, yeah.

7:30Conan O’Brien:And he will be hosting the 98th Academy Awards. So, Conan, come on down.

7:39Craig Robinson:Hey, it's my friend, Conan. Oh, we did? Oh, hi. Hi, hi.

7:44Conan O’Brien:Well, you came in like, you got work to do. Yeah, I just had a lot of sugar this morning, so.

7:50Craig Robinson:I think you probably have a lot of sugar every morning. I mean, it's not like you, you know.

7:56Michelle Obama:You know, it's funny. this is a true story, but I have always had a lot of manic energy. And about 10, 15 years ago, my doctor retired. So I went to see a brand new doctor for the first time. And he's running me through the checklist of this, this, this, just wants to get to know me. And he said, he finally got to this one part of the checklist. And he said, now let's talk about drug use. And I said, which is true, I've never done drugs in my life, never tried a drug, never wanted to get into that. So I said, I've never done any drugs. And he said, let me ask you again about your drug use. And I said, I've never done any drugs.

8:39Michelle Obama:And he said, what about cocaine? And I said, this is true. I said, no, no, this is 100 % true. And I said, I've never done cocaine. And then he put his clipboard down and he said, this questionnaire doesn't work if you're not being honest with me. And I said, I'm being honest with you. And he said, I've seen your work. And he just assumed that I'm all coked up. And I'm saying this comes naturally for better or worse.

9:07Craig Robinson:I was born this way.

9:08Michelle Obama:Yeah, this is the way I mentioned this a bunch, but my dad was a doctor and a scientist. Right. And maybe after 15, 20 years of being on television, he looked at me and he wasn't trying to be funny. He just said, I think I understand. You are making your living off of something that should probably be treated. And I said, I love you too, dad.

9:32Craig Robinson:How old were you when he gave you that observation?

9:36Michelle Obama:Well, I was, I mean, I think he had seen me do the late night show. I mean, I might've been in my late 40s when he said that.

9:46Craig Robinson:Oh my God.

9:46Michelle Obama:Yes, this was not something he said to a, you know, this was him looking at the arc of my life and seeing that all of this nonsense that comes out of my head and the crazy energy, in another era, they would have treated me. You know, they would have put me in a special - Or admitted you. Admitted me, yes. That's the nicest thing you've said to me in a while. Put me in a facility of some kind. But now we live in this weird, I mean, it's all when you're born. It's such luck. But in another era, my people in Ireland, you know, standing around and we're supposed to build a stone wall. I wouldn't have been helping with the stone wall.

10:26Michelle Obama:I'd have been off to the side doing bits and going, yeah, and then this guy and then that. And they'd be saying, this idiot doesn't do anything.

10:32Craig Robinson:Are you unique in your family? Because you have a big family. Yeah, I'm one of six.

10:38Michelle Obama:I will say my siblings are really nice. They're really smart. They're sweet.

10:44Craig Robinson:Do they do drugs? No, they do not.

10:48Michelle Obama:I think we all should. But no, they don't. It is, I see a lot of similarities with my siblings. We all have sort of the same stuff and it comes in different versions. They're very creative. They're all really funny. And then I just happened to match this particular time in history when we have television and podcasts and places where people like me can actually do this and put a roof over our head doing it, which I don't think existed. You know, it took just in the last, you know, 100 years for this to come along.

11:30Conan O’Brien:Well, you said they're all funny. Where does that come from? Were your parents funny? Was your kitchen table funny at dinnertime?

11:37Michelle Obama:Yeah, yeah. Yeah, everything starts at the kitchen table. For us, it was Sunday dinners. My mom always insisted that we all eat together. We have a Sunday meal after church. We come back, we sit around this round table and we would have our meal. And then people would jockey for who's the funny one at the table and who can really make mom and dad laugh. And especially my dad, when he would laugh, repressed Irish Catholics. And you see this thing that every culture has, what's the key where they're allowed to lose their control a bit? My parents didn't drink. Obviously, there's no drugs. There's no, no one talked about sex.

12:28Michelle Obama:So there are all these areas that are off limits, but you're allowed to be funny and laugh and you're allowed to eat tons of fried ham. And those are the areas where we're allowed to like let our hair down. And so my dad, when he would laugh, my mom had a great laugh. My dad would like hug himself and he would kind of clap himself and hug himself and rub his hands together. And huge fan of you and the president. and I brought him to an event I did once in Washington, D.C. and he got his picture taken with you guys and the president was so nice. He said, yeah, yeah, hey, Conan, dad, dad, get over here.

13:20Michelle Obama:And he made it all about my dad. Yeah. And my dad, for the next 15 years of his life, just had the picture with you guys and your daughters were kids then, but they were in the picture too. And that was something I think, I think he lived another 10 years because of that. Talked about it nonstop. Oh my gosh. So, but so much of my career was, I think it all began with trying to make the parents laugh.

13:51Craig Robinson:Yeah.

13:52Michelle Obama:And that's where things start. And you can then later on, it can become, oh, I'm hosting the Oscars or I've got a late night show where I'm doing this big deal or that big deal. But it's really no different. You're still in some way trying to make them laugh.

14:08Craig Robinson:Yeah.

14:08Michelle Obama:You know, and I think just like the two of you, you're probably for the rest of your life going to be trying to live up to what your mom or your dad would want. And that stays with you. And I'm a big believer in we lose these people, but we don't lose them. Oh, for sure. They're with you. Oh my gosh. And they're why you still, a lot of people would say, you two are good. You're good. You can let your hair down now. You can, but you are trying to still live up to that standard. And I think that's what I'm trying to do with my parents.

14:51Conan O’Brien:Hey Mish, you remember we used to go on road trips and mom used to meticulously pack the trunk of car with plenty of food, like fried chicken.

15:00Craig Robinson:And it never tasted better than in the backseat of a car.

15:04Conan O’Brien:Man, coming out of the tinfoil, you know, it was really good. And it would, pound cakes, cookies, the whole nine. And I remember it'd be a treat to even get flavored potato chips because, you know, mom would say, let's just get the plain ones. No barbecue, no salt and sour.

15:21Craig Robinson:Not a lot of extras in the Robinson household.

15:24Conan O’Brien:No, no. But now, you know, the difference is night and day when I travel with my family.

15:29Craig Robinson:What do you think? Yeah. I mean, you know, mom would have to pack for us staying in a place a long time. So it wasn't just snacks for the car because you couldn't just get anything you wanted. So she had to come on vacation with everything she needed for the week, which seemed like a hassle. Yeah.

15:48Conan O’Brien:It was like we had the whole trunk of the car was a grocery store. Now, are you particular about your snacks? For example, I like my cheddar cheese, but I want it cut on blade number one.

16:00Craig Robinson:Really?

16:01Conan O’Brien:What about you? Yeah, I like mine thin. I like my cheese cut, sliced thin.

16:06Craig Robinson:I don't think I'm that particular. I think a snack is a snack.

16:10Conan O’Brien:Well, now when I travel with the family and we book a stay on Airbnb, I have the convenience of having our fridge stocked with our favorite snacks or anything we might forget or don't have.

16:22Craig Robinson:We could have used that when we were little.

16:24Conan O’Brien:How about it? As a matter of fact, Kelly always uses Instacart when we're on vacation. But with this new Airbnb plus Instacart partnership, I love the convenience this feature within Airbnb services to order our groceries on Instacart. The partnership allows you to seamlessly book with your Airbnb reservation before or during your trip. I might do some cooking during my stay this time because our groceries will already be there when I arrive. Making it feel like home from day one.

17:03Craig Robinson:You're manic, you're silly, but you are wicked smart. Oh. I mean, and so was your family. I mean, I love hearing about the fact that your mom went back to law school. Can you talk about her? Yeah, my mother. She's a badass.

17:19Michelle Obama:So both my parents were the first ones in their families to go to college. Um, they, you know, everybody's got an immigrant story. Everybody comes from someplace else.

17:31Craig Robinson:Yeah. Let's say that again. Yeah.

17:33Michelle Obama:No, we all, I mean, I, I, last night I was, uh, trying some Oscar jokes out in a comedy club and I took an Uber home and the driver's from Jordan and he recognized me and we started chatting. We had the greatest chat on the long ride from East LA back to my house and just a wonderful talk. and he put me on the phone. He said, can I call my daughter? And I said, sure, she's 25. So he's a Jordanian immigrant. His daughter is taking her MCAT. She's gone to college. And I just was telling him, this was our story too. We came to this country, late 19th century.

18:17Michelle Obama:And there's a lot of people not too thrilled to see the Irish in Boston. So my people moved out to the central Massachusetts and worked hard and I think had good values. And then my mother grew up in Worcester, Massachusetts. Her father directed traffic in downtown Worcester. One of the funniest people I've ever met. I remember my grandfather really well. We called him Hoofer because he knew some dance moves. And so everyone called him Hoofer. And you got none of those jeans. I didn't get those. Look, if I knew I was getting slammed on this show, I would not have been. Okay. You don't have to take that from that.

18:59Michelle Obama:Apparently I do. Yeah. You don't. Apparently I do. So my mother worked hard and she got a full scholarship because they didn't have, her father earned$55 a week. So she didn't have that kind of money. She got a full scholarship to go to Vassar, which was a big deal. And then she went to Vassar. And when she graduates, she gets a full scholarship to go to Yale Law School. She goes to Yale Law School. She leaves and she goes to a big law firm in Boston. She clerked for a state Supreme Court justice.

19:36Craig Robinson:But she also raised, this was after she had kids, right?

19:40Michelle Obama:Well, it was before she had kids. and then she just started a law firm when she started to have kids. And then she had to take time off.

19:50Craig Robinson:Because she had a lot of kids. She had a lot of kids. You guys just kept coming and coming. I mean, I swear to God,

19:58Michelle Obama:I think she had a child every four months. Medical science is still trying to figure out how the Irish can do that. But yeah, I think my brother Neil is 61. It was born in 61, Luke in 62, me in 63, Kate in 64. I mean, no one ever knew my name in that house. You know, and then there's Kate, Jane, Justin.

20:24Michelle Obama:And she went back to work.

20:28Conan O’Brien:Wow, she went back to work after. So how old were you all?

20:31Michelle Obama:I would say she went back to work when I was about, I want to say nine. I was not happy about that because I love coming home and my mom was there. But she went back to work. but she had stories of the early days, early 1960s when she is a graduate of Yale Law School and she's working at a big firm and she would go to a meeting with other lawyers and then they would take a break to go to lunch and they would all go into the dining room but she couldn't go in because it's men only. And so I would ask her, did that make you angry? And she said, oh no, it was just the way it was. And she said, they set up a card table for me.

21:19Michelle Obama:I sat outside and two of the lawyers were very nice and sat with me. And so there was this, I think it gets overlooked sometimes, but there's a thing that happens with people who are on the front line of change. Sometimes you think they're going to be angry. sometimes they're not because they think, I don't have time for this. That's right. I've got to win. I got to get the win. So she got, she worked hard. She became a partner. And I think she was, you know, maybe the second or third woman to ever be a partner in this big law firm.

21:58Craig Robinson:Well, you may make a good point that, and I want young people to understand this because sometimes when change has happened and the younger generation doesn't know what it takes, they can be a bit judgmental about what it took for those two, the kind of mentality, the kind of, because there's some young women who say, well, why didn't you speak up? And why didn't you use your voice? Or look at an older generation and say that, you're allowing something to happen without understanding the context of the growth.

22:33Michelle Obama:Yes.

22:34Craig Robinson:And I think that's why sometimes we get in the way of change because the younger people want it, think it should look different. They think the attitude should be different. And you just, your mom knew what she knew, being the first woman, the only woman to ever practice law. Yeah. And then to make partner, you know, what kind of compromises your mom had to make to get there and she needed the job too. She had six, how many of you all?

23:02Michelle Obama:I don't even know. I've tried to count my siblings and there's just two more, too many. I can't do it. But the, yeah, it reminds me a little bit of that. There's that Jackie Robinson ethos where because he was the first, he felt he had to be completely above reproach.

23:23Craig Robinson:I know a little bit about that.

23:25Michelle Obama:Yeah, well, that's what I'm saying is the, you know, I think I could tell when you and I took a trip once to visit a big giant military base in the Middle East. Which was an amazing trip.

23:45Craig Robinson:It was an amazing trip.

23:46Michelle Obama:I could tell that you and your team were being so careful that everything is done by the book, that there's no perks. I was really impressed with that. And it occurred to me then, oh, I see, everyone feels we need to be so, so, so far beyond.

24:13Craig Robinson:It wasn't even a feeling. It was the truth.

24:15Michelle Obama:It's the truth.

24:16Craig Robinson:I mean, there's absolutely no way that the behavior in this current administration would have been accepted by the first black family in the White House. So fortunately, it wasn't difficult to do because we are those people. It wasn't difficult to follow rules. It wasn't difficult to have high standards. It wasn't very difficult because in order to get where we are, as you've seen and your mother, you don't get here without being damn near perfect. We don't get to fail two, three, five, seven times. We don't get to file bankruptcy over and over again and still be considered a successful business person.

24:58Craig Robinson:We don't get to not be at the top of the class. Every I has to be dotted, every T has to be crossed. And your mom was among the first to begin to pioneer that firstness.

25:16Michelle Obama:Yeah. And I think because the big game changer for Irish Catholics in my parents' generation was John F. Kennedy. and you've got this very glamorous first family and they're Catholic and Irish, I think that made a huge difference for people in my parents' generation and made a big difference for me because they made it cool. They made it cool to be Irish and then I made it uncool. Speaking of - When John Kennedy gave us, I took away. Were you a cool kid growing up? God, no Have you seen his pictures?

26:06Conan O’Brien:You know why? Why would you ask that with a straight face? Here's why When I first met you You were surprised how tall I was As I of you And the first thing I thought I'm sure he was an athlete in high school And one of the cool kids And funny in the locker room That kind of thing So I want to get that Tell me about that What happened? Let me explain to you what happened, sir.

26:32Michelle Obama:I was, my height came late. So I was one of those guys who had a growth spurt kind of later in the game. Okay. So I recently saw, someone found footage of me in, when I'm 22, I'm just out of college. And I think I look like a 14 year old. Really? Yes, of undetermined gender. And I look at that person and I think you're 22.

27:03Craig Robinson:So you weren't, you didn't get your height then?

27:05Michelle Obama:No, no, I had my height by then, but I was 6 '4". When I moved out to LA to start my career, I was six feet, four inches tall, I think 155 pounds. Okay. Now I ask any engineer who's listening, do the math on that structure. It will collapse.

27:22Conan O’Brien:It is going to break.

27:23Michelle Obama:It's going to go down. and if a moth lands on it, it will collapse. So there was no, you know, people sometimes say, because I make fun of myself a lot and they say, well, that's kind of an act. And I go, no, no, no, that comes from, I think obviously they know now your core personality is formed fairly early on. And then you do little finishing touches to it. but by the time you're 15, 16, 17, it's there. And those were years for me where I didn't feel, I was not cool. I was not a good athlete. My brother, Luke, who's a year older than me, is much smarter than me. My brother, Neil, was much stronger.

28:10Michelle Obama:And I just thought, I don't have anything to offer. I really thought that for a long time. And it took me a while. It took me a long time to kind of put it all together, which is why when I say I find myself kind of ridiculous, it comes from a place of honesty. Like that was my personality growing up. And so I was funny with my friends, but I was not the class clown. The class clown, I maintain, usually ends up in like a motel shootout. The class clown, the guy who gets up and changes the clock forward and is, you know, throwing stuff out the window. They're in prison soon after high school. I was not that guy.

28:59Michelle Obama:I was joking around with my friends. And then when the teacher came in, I was really quiet and a nerd. So that's my story.

29:09Craig Robinson:But it got you to Harvard.

29:11Michelle Obama:Yep.

29:12Craig Robinson:Which is where a lot of funny nerds go.

29:15Michelle Obama:Yeah, I didn't even, you know, the irony is as a kid, I dreamed about being in show business and I loved comedy. And that's how my dad and I really bonded. You know, you're always trying to like, I think a lot of boys look at their dad and think, how do I key into this person? How do I, you know, he can be formidable. I'm not sure how I can really connect with this person. and then we would watch comedians together. We would watch comedic movies and I would see him laugh. And that was where my interest started. And I started doing things and loving the idea of getting to do comedy. And then I thought, I'm in Boston, Massachusetts, Brookline.

29:59Michelle Obama:Nobody within a thousand miles is in show business. I've never seen anyone in show business. That's not a real thing. I got to find another way. So I decided I want to go to a good college and make something of myself. So I'll just become a grind. It's not a glamorous story, but I was a grind. And I was grinding it out in my little room, memorizing things. And I...

30:22Craig Robinson:What did you think you wanted to be?

30:24Michelle Obama:I thought, well, I'll be... What was the pursuit? I will be a serious person. I'll be an editor of a newspaper, or I'll be an academic. Were you an English?

30:33Craig Robinson:What was your major?

30:34Michelle Obama:I loved English. I was a history and literature major. And I thought, that's what I'll do. So I get to, I achieved that goal. I get into Harvard. Didn't think I was going to. I did. I think now it's time to become the serious man of letters. And someone said, I'm going to go to this meeting of something called the Lampoon. And I said, I've heard of that. That's pretty famous. Yeah. And I said, maybe I'll tag along.

31:00Craig Robinson:Was this first year?

31:01Michelle Obama:This was first semester freshman year. I was at Harvard for two maybe weeks. And so I went and there's this kooky little building there. And I sat on the floor and they come in and we're all sitting on the floor. And they talked to us and they said, it's very competitive, but you all have to submit funny stuff and we'll see what happens. And I said, I'll give it a try. And made it through the first cut, made it past the second cut, made it through some other things. And then the next thing you know, I'm a first semester freshman and I'm on the lampoon.

31:32Craig Robinson:And that's so I was hooked. Let me just explain to the listeners. I equate the Lampoon to like the Harvard Law Review of comedy. I mean, it is considered very flattering. But it is.

31:48Michelle Obama:It was a huge deal and so many famous, funny people and great, right? John Updike had been on The Lampoon and, you know, Robert Benchley and the guys that created National Lampoon and did Animal House. And I mean, it all came, all this great stuff came out of The Lampoon. And it was unusual to be selected as a freshman. I think, yeah, it was a little bit unusual. And then I gave my whole life to it. It was one of those things where I felt like I had a calling. Up until that point in my life, I thought anything that I achieved, and this is very Catholic, but I'm sure it's not just Catholic. It's tons of religions and cultures.

32:39Michelle Obama:I thought anything good has to come through suffering. So I really suffered to do well on the test. I really suffered. I really suffered. I had a lot of anxiety. And then I would do well on the test because I suffered. This was the first time in my life that I would say, hey, what about this? And people would say, that's great. And I'd say, really? That was easy. That was easy. I had fun. Wait a minute. I had fun. Yeah. Didn't take a lot of time. Yeah. And now people are reading it and laughing and I'm getting that same dopamine hit I get when I make my dad or my mom laugh, what's this all about?

33:21Michelle Obama:And then I was hooked. I mean, I said I don't do drugs, but this is to me the most powerful drug. And it goes for all of us. When you find that thing that gives you joy and then you realize that, you know, in whatever, hundreds and hundreds of years ago, people thought the greatest thing would be able to turn, you know, lead into gold. I think the closest thing I've seen to that in life is when you can do something that gives you joy, but it gives other people joy too. And then someone hands you$20 afterwards, a check. I hope it's more than $20.

33:59Craig Robinson:Maybe that's just a little bit more than you'll make for the Oscars. Yeah, probably.

34:05Michelle Obama:I haven't even looked into that yet, but I'm sure I'll lose money. But that is, to me, that is magic in our time. Yeah. Is when you can do something that, and you both experienced this where, wait a minute, I'm having fun. Yeah. I'm doing what I think I was put here to do. And other people are thanking me. That's insane. So that to me was when I got that first hit. And really everything has just been an extension of that. When I called my parents senior year and I said, I have to give this comedy thing a try.

34:41Craig Robinson:Yeah.

34:42Michelle Obama:And I talked to them as if I was becoming a monk. I said, look, there's probably no money in it. And they were -

34:48Craig Robinson:No one will marry me.

34:48Michelle Obama:Yeah, no one will marry me. And that was true for a long time. And then, you know, it's really just all that happened then. And then everything else has just been moving the little chess piece a little further forward. And now I'm here talking to the two of you. So that's the miracle of it all.

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38:31Craig Robinson:After Harvard, did you immediately, you were able to?

38:36Michelle Obama:Yeah, I had a good friend in school. I knew that the thing I had to do was go out to LA. that I needed to go out to LA.

38:45Craig Robinson:But not New York? Why LA versus New York?

38:47Michelle Obama:There wasn't a lot of work in New York. Okay. There really wasn't a lot of work in New York. And a lot of the work was in LA. And so I said to a really good friend of mine in college, Greg Daniels, who went on to create, I mean, most of the great TV shows of the last 25 years, The Office, Parks and Recreation, King of the Hill. I mean, co-create that. And he's, you know, just has this huge career. But at the time, we're two pretty nerdy guys. And we're newly 22 years old. And I said, do you want to do this with me? And one of the things that was really key was he was... Greg's a really funny guy.

39:36Michelle Obama:But he was also... like an ethical, good person. And I thought, I don't want to go out there without a friend who's with me, who I know to be a really high quality person. And yeah, rule number one has got to be funny. And he's clearly, you know, hilariously funny, but also really good work ethic and a good person. So we went out together and, you know, we started, we got some work on a show called Not Necessarily New News, which was on HBO. And this is HBO back when, if you wanted to watch the show, I think in those days, I'd have to tell my parents, you need to go check into a motel. Hey, check out my show.

40:24Michelle Obama:What's it on? Is it on NBC, CBS? You need to go to a motel. And yeah, it was like I was working in porno or something. We'll just clean that up. Anyway, it was, it was, but it was a start. We got started. And then the first thing.

40:42Craig Robinson:And earning a salary. Earning a salary.

40:45Conan O’Brien:And this was right away because the comedians we have on and the performers, they all go out. Yeah, we do the same thing, but they're struggling for a period of time.

40:55Michelle Obama:We were lucky. We got that gig right away. I knew I wanted to perform. So I started going to do improv at night. And so I would work in the day and write. And then I would go to these little places where you put a$10 bill in a jar, and then you get up and you do improvisational scenes with other people. And my first time that I went to an improv class, I noticed, I was looking at everyone else because it's the same thing if you're an athlete, whatever you're doing, you look around and you try an eye. size up size up people and who's the one who's like okay they're good they're good I walk into this place that's on La Cienega the Coronet Theater and it's this tiny little room and there's a teacher there Cynthia Segetti and you you put your money in the jar and then you get up and she had us doing different exercises and I'm looking around the room and I'm going no no no no who is that she's good she's really funny and her name was Lisa Kudrow going on to be in Friends and I didn't know this but at the time she's looking around the room doing the same thing

42:05Craig Robinson:and she's like

42:06Michelle Obama:okay that guy the guy that's 155 pounds

42:10Craig Robinson:I was like I wasn't gonna ask how much did you weigh then

42:12Michelle Obama:now I weighed 156 pounds I had a bagel and so then I started working with her and we became really good friends and I started meeting other people Then we lost the job that we had because they had to downscale the staff. So I think Greg taught SAT prep. And I went to work for Wilson's House of Suede and Leather.

42:37Craig Robinson:Really?

42:38Michelle Obama:Yeah.

42:38Craig Robinson:That's true. And it wasn't even... It's like, I have to check. Yeah.

42:41Michelle Obama:No, no, I'm telling you.

42:44Craig Robinson:Of all the shops, you picked Wilson's House of Suede and Leather?

42:48Michelle Obama:You know, I want to give them a plug. I think I went to a temp agency and they assigned me there and they didn't put me on the floor because I did not look like a guy who could pull off any kind of leather. So they put me like in an office situation and I wasn't too happy during that period of my life. But then we got another gig and then we end up on Saturday Night Live. So we moved back to New York and then I go to the Simpsons.

43:16Craig Robinson:So you end up writing for SNL.

43:18Michelle Obama:I'm writing. And then I'm on The Simpsons. And then I was always the writer who would get up on a table and act things out and make the other writers laugh. And so when it came time to find someone to replace David Letterman on his late night show, I worked for Lorne Michaels and I give him all the credit. he told NBC, have you thought about this guy, Conan? And they said, the writer?

43:53Craig Robinson:Yeah.

43:53Michelle Obama:And with the hair and the weird name. And then he said, you know, I'm just, and they said, well, Lauren, if you'll vouch for him, he can audition. And so I auditioned and I had a really good audition because I didn't think I had a chance. Yeah, that's always the way. And so I thought, I'm never getting this. This is the biggest star on television next, you know, I'm going to replace him. and I'm just this guy who's 29 years old. I'm still like, oh, my skin broke out again. It's still happening. And then I just went into that audition and had a blast.

44:31Craig Robinson:What do you think prepared you? I mean, I think late night talk show hosting is one of the hardest things. I mean, it's just hard being on the show.

44:40Michelle Obama:I think what helped me the most is at the time people said you need to be a stand-up comic, which I had never done. I'd done a lot of improv. They said you have to be a stand-up comic to be a late night host. And I found that the improv training was all about looking at people and listening and looking for what's funny organically. So I found that to be hugely helpful.

45:08Conan O’Brien:I've heard you talk about being able to take advantage of all the great luck that you've had. And that warms my heart because as a coach and as a player, as an athlete, you're always taught that the most prepared person is also the luckiest.

45:29Michelle Obama:Yeah, yeah, yeah. It's that old saying, you make your luck. I think, first of all, I got just the time in which I was born. Right. I am a poster child for incredible luck. I've been very, very lucky. And I give it up for that. I also know that I work really hard and I prepare and I try to treat people the right way. But I get very angry when people don't give it up for luck. And I'm also really aware that, you know, as a, you know, what was my path like as a white male coming up in the 1980s, 90s, a lot easier than a lot of other people in comedy and probably in any profession. So take a second, give it up for that.

46:20Michelle Obama:Don't have an attitude about it. Be grateful and then -

46:24Craig Robinson:And then don't shut the door on everybody else.

46:27Michelle Obama:Oh no, shut the door. I disagree completely. Shut that door and nail it shut. But once you get in, don't let anybody else in. That's the message of this episode. Yeah, no, exactly. Yeah, and that's one of the things. I mean, I noticed it today. I show up and you've got all these great young people. There's great music playing. Everyone looks like they're, you know, 20, 21, 22. And I get -

47:02Craig Robinson:Except for Dan.

47:03Michelle Obama:Except for Dan. Yeah, Dan and listen, you served your country in the Korean War and we appreciate it. 110 years old. But I feel, I get so much energy from young people. And whenever, when I see young people that are really funny, I choose not to be threatened. I choose to be excited. This person, this guy, this girl, this person is great. They're terrific. they really make me laugh. I want to enjoy them. I want to try and help if I can. And just anything, people, I know your husband feels the same way, but I'm always preaching optimism to my people and cautious optimism. I always say I'm like a 51, 52 % optimist.

47:57Michelle Obama:But I do say the world has always been filled with horribleness. There's always been trouble. And this, when young people preach to me, it's all over or say it's all, it's the end of the world. And I say, you have to understand this is the way it's always been. And this is how it feels. And it reminds me of this great scene in the movie, The African Queen, Humphrey Bogart, Catherine Hepburn, they're in his boat. They're lost in the weeds. It's a great metaphor for life. They're trying to get out. They're trying to get out. He's pulling the boat with a rope. It's covered in leeches. He gets back in the boat.

48:39Michelle Obama:And finally, he gives up. And she gives up. And he says, we're never getting out of these weeds with this boat. We're never getting out of here. And they give up and they say, we're just going to die now. And the camera starts to, they kind of pass out. And the camera slowly pulls up and you see it starts to rain and you see that their boat is about 15 feet from a massive river. They just don't know it. And then the water rises and when they wake up in the morning, they're on the river and they're safe. And I always think about that. I think there've been probably 35 times in my life when I thought - Were you been dead on the boat?

49:18Michelle Obama:I thought I was on the boat and I'm dead on the boat. I am not going to make it through. I'm not going to get to the college I want to go to. It's over. Now I'm in the college, but I'm not going to. I made that, but I'm not going to get the career. Then you get part of it. Oh, no, I've got this late night show, but critics hate me. and everyone says this was a mistake. This kid who gave him this job. There's no way I'm going to make it. Everyone's saying you'll make it a few months, but then you're out. And then I make it past that. But then later on, I get the Tonight Show and I think now I'm in good shape.

50:06Michelle Obama:Nope, that blows up. And I thought now it's really over. No, it's not. it keeps happening over and over and over again. And then it's just learning. To roll with it. To roll with it and say, okay, what's my next opportunity? Reset, recommit, and look for the next opportunity. And that is something I try to impart to my kids.

50:44Conan O’Brien:My mom really liked meeting you.

50:48Michelle Obama:Oh, that's nice.

50:49Conan O’Brien:She really liked meeting you. So we, you know, and I used to, I live a train ride away from her. So I visit her all the time and we talked about, oh yeah, it was really fun getting together and seeing, but that Conan, he was just such a nice. That's nice. So you should know that. Oh, well, that's huge for me.

51:09Craig Robinson:That must have helped you land a beautiful wife.

51:12Michelle Obama:I don't know what I did there. Who is one of my favorite people. I just got, yeah, my wife, Liza, is pretty incredible.

51:17Craig Robinson:How'd you guys meet? We met, I was out doing a field piece.

51:25Michelle Obama:And how those work is there's a silly idea. I say, okay, I'll do it. And then I show up someplace and we shoot cameras out. Which bit was it?

51:33Craig Robinson:Were you in it? I was in it.

51:35Michelle Obama:It was a bit where, it's a long story, but there was a really, we decided it'd be very funny if I went to a top advertising agency and pitched a terrible idea.

51:46Craig Robinson:I just love these bits.

51:49Michelle Obama:And, you know, my favorite spot is me being very confident about something that's really stupid. And so I went in, and so it was my idea, it wasn't my idea, it was someone else's idea, but my job was to go in there and go, let me tell you something. And these are the people that do like, you know, Air Jordan ads. The best of the best in the room. And I'm supposed to go in and pitch them the worst idea and have total confidence in it and almost treat them with contempt if they don't get what I'm saying. So I go into this room and I start doing my thing I do. And I do one person, one person. And then I start talking to this woman.

52:32Michelle Obama:And I immediately stop being funny. And I just start saying, oh, so, oh, okay. So you, and then did you write a, so, oh, I see. So you got your degree and huh. And then she went, yeah. And I was like, no, no, no. We'll see. Yeah. But what I did was I, I studied this, but then I did that. And we were just talking about the most mundane stuff. It wasn't comedy. I wasn't even trying to be funny. And my producers are, they got the

52:57Craig Robinson:headsets on. It's like, what is happening? They're like, what's he doing?

53:00Michelle Obama:What's he doing? This is death. What's he doing? And then we chatted for a long time. And then I finished up the segment. And then my head writer, Mike Sweeney, who's still my head writer and working with me on the Oscars and does an amazing job. But he was like, what was that all about? And then I said, I don't know, but maybe we should get everyone's contact information. And he said, why would we need their contact information? And I said, I don't know, editing? He's like, that doesn't make any sense. Editing? What are you talking about? But the next thing you know, we just start talking on the phone.

53:41Michelle Obama:So we didn't even have a set. That's not even a date. We just met. And then we just talked on the phone. How old were you? I was 35, maybe. I was no spring chicken.

53:52Conan O’Brien:So you completely ruined the bit because you saw her.

53:56Michelle Obama:They fell in love. They salvaged the bit, but you know what's great? You can look it up. you can say Conan meets his wife. Conan meets Liza. And you can see me. I look still like, you know, now I'm 35. So I look like a 20 year old girl. And I'm there going, oh, hey, how are you? And you can see us talking to each other. And it's online. And I've never watched it because I know what the real experience was. I don't want to see it. But we ended up, you know, dating. And then we got married and kids. And it's been, I think, we got married in 2002. So I didn't go to a good school. I can't do the math.

54:39Michelle Obama:Yeah, I'm not even trying. That's a neat story. It's a great, yeah. And it was really nice. And, you know, it's crazy. Liza's mom watched it at home. She stayed up and watched it at home. Her dad was like, I'm going to bed. I don't need to see. and she was like, our daughter is going to be on national television. The bit's airing tonight. He didn't know anything about us. You know, we hadn't even chatted yet. We had met, but that was it. We hadn't even talked on the phone yet. But Pam, my wife's mom, she stayed up and she watched it. And in the morning, she said to Jake, unless that guy's an ax murderer, he's going to be our son-in-law.

55:23Michelle Obama:No way. And they said, But she said that to more than one person. Wow. And they said, what are you talking about? Yeah. That TV show host who had a brief exchange with your daughter is going to be your son-in-law. And she went, I just think that's what's going to happen.

55:37Craig Robinson:Wow.

55:38Michelle Obama:And it happened.

55:40Craig Robinson:She knew. She knew. And I know that Liza just lost her mom. Yeah, she just lost her mom.

55:46Michelle Obama:Sorry. But, well, you guys have been through it too. It's just one of those. It's too profound to even contemplate. But I think the thing that is some consolation is we... And these people are with us. They're in us. Like we didn't lose them. And I really believe that. And you don't even have to be spiritual to believe that. They imprinted on us and they're with us. So you're always going to have your mom. I'm always going to have my parents. Liza's always going to have her mom. They live on through us. We just lost Catherine O 'Hara, who is one of the, you know, maybe possibly one of the, I mean, not possibly, but one of the great, great, great, great comedic actresses of all time.

56:49Michelle Obama:And at the same time, one of the best people, just a lovely, lovely person. And talk about walking the walk. She really showed up for everybody. and Martin Short gave the eulogy and he just said she's with us. We didn't lose her. She's with all of us. She imprinted and her work is with all of us and so that's what I take away from the whole thing.

57:14Craig Robinson:And sometimes I literally my mom comes out of my mouth. You know? Yeah. And I'm noticing it more and more when I say something and I'm like that was mom.

57:25Michelle Obama:Yeah. Yeah, yeah.

57:27Craig Robinson:It's like I even I hear it I was like, oh my God, she just. Yeah, yeah. Yeah, yeah. So, so.

57:36Conan O’Brien:Well, I want to talk about the Oscars because you said something right when you came out that you went to do, you went to a comedy club to try something out. Can you talk about that whole process to somebody like me who's sort of not in the, and probably our listeners who don't get a chance to talk to someone.

57:58Michelle Obama:If you'll explain to me how to be an athlete, then I will explain it. I can do that. If you would work with me for a five-year period.

58:05Conan O’Brien:Listen, I love developing talent. Okay, well, I have no talent in that area. So good luck to you.

58:10Michelle Obama:Perfect.

58:11Conan O’Brien:I'll have you making shots in... Oh, really? Two weeks. Yeah, okay. Yeah, really.

58:16Michelle Obama:I like to be that guy that's way, way outside taking up crazy three-point shots that don't go near, but with total confidence. And I love to shout stuff out when I'm doing it. And a freeze. Yeah. And then freeze and do that look of like, deal with it. And it doesn't even hit the rim. It misses the backboard. Okay.

58:37Craig Robinson:That's the next bit. That's the next bit.

58:39Conan O’Brien:Yeah.

58:39Michelle Obama:That's it.

58:40Conan O’Brien:Where you have a coach who's working with you for weeks.

58:43Michelle Obama:And you have all the attitude. That's all you have. I did this. I did a thing with Magic Johnson. We shot a thing where I think we played a game of horse together. And I'm just being such a clown. But he was so funny. making fun of me. The way I shot, the way I moved. He starts to imitate me at some point. It was, that was a dream come true. The Oscars, one of the, there's a lot of different parts of it. And you start thinking about different bits and what could we do for pre-tapes? What could we do? What kind of production number could we have? But you're always thinking about jokes. What could the jokes be?

59:22Michelle Obama:And you really want to test them. And one of the ways to do that is to go out to clubs. And what I like to do is go way, way, way, start way far out. So we went to Covina, which is way out there. I mean, I think I was driving for almost an hour, got to Covina and you go into a club and you're a surprise. And then you read a bunch of Oscar jokes. And it's fun because you make them part of it. You say, look, if you guys laugh at a joke that isn't good, that might convince me to do it. and then I'm going to die on the Oscars. So don't do that to me. And so they're laughing at the part where you're not even reading the joke.

1:00:03Yeah, yeah.

1:00:04Michelle Obama:I love that. And I've gone to a couple of clubs like that. I did one last night. And you just go way out there. All of them, they're the same. They're the same in that you're in some back room or an alley standing around with other comics. And you, this is a lesson I've learned again and again and again, which I actually find kind of filled with hope, which is you think you've gotten to this other level where it's like, well, I'm hosting the Oscars and I'm going to walk out at the top and have a tuxedo. But I'm in Covina in an alley and I'm hanging out and someone's got a ventriloquist dummy and I'm waiting for my, you know, I'm waiting for my turn to go out there.

1:00:46Michelle Obama:Did you? You did that on purpose. No, I didn't. The reason why everybody - I did not.

1:00:51Craig Robinson:Who told him?

1:00:52Michelle Obama:What? I don't know what we're talking about.

1:00:54Craig Robinson:Craig loves ventriloquism.

1:00:57Conan O’Brien:I honestly, I swear to you. I swear to you. I don't trust you. You're too funny.

1:01:03Craig Robinson:We've been talking about this episode after episode.

1:01:07Conan O’Brien:You don't. I do not.

1:01:08Craig Robinson:He is, I think, the last person who believes that ventriloquism is a lost art. Is an underutilized performance vehicle.

1:01:19Michelle Obama:When you see a good ventriloquist, it is really funny. How about it? And I'm going to side with you on this. When you see a really good one, it's really funny. It's so funny. See? Okay. All right. Did you put him up to this? No, no. Listen, I'm going to tell you something. I don't know anything about this. You're linked to ventriloquism. I swear to you. I swear to you. I would tell you right now, but no one said, hey, you want to get crying? Mention ventriloquism. I did not do that. I just mentioned like, that's how kooky it is when you're in the alley. Right. And I love that. I love that it's this constant dance between put on the tuxedo and you're in an alley.

1:02:00Michelle Obama:Yeah. In a t-shirt and jeans.

1:02:02Craig Robinson:Do your nerves get, I mean, I watch you walk on stage to this audience of every famous person on earth. And you know, they're not a regular audience. They're not a regular audience. They're nervous. They're looking at themselves. They're very self-involved. They're deeply self-involved and self-conscious. And you're out there to be funny. I mean, does that change the nature of it?

1:02:28Michelle Obama:It's a very different audience. Like when we would do the White House Correspondents Dinner, and I did that once under your administration. And I remember I got to sit with you, and it was really fun because you were so nice to me that night. We're sitting up on the dais. But that is not a normal crowd. That is a crowd of people that think they're the coolest people in the world. And they're there. They're thinking a lot about their own world. And you need to be funny, but you can't act like you know too much because then they'll resent you for that or think you don't belong. And so everything is this incredible long period of preparation to gauge what's going to work in that room that doesn't go too far this way, doesn't go too far that way.

1:03:21Michelle Obama:and I've talked to your husband about this. They make you follow the leader of the free world. He goes first.

1:03:27Craig Robinson:Right, really.

1:03:28Michelle Obama:And kills it. And then before -

1:03:31Craig Robinson:Well, usually they don't. Yeah, yeah. Well, I know. The format usually works in the best interest of the host.

1:03:38Michelle Obama:The president we're discussing, unusually good at that. And then he would finish, like drop the mic, crowd going crazy and a voice would go, where's John McConaughey O 'Brien? And you're like, well, that's it? And you're walking up and you see people like, what, who would go now? And so you got to wade through that a little bit. But it's all calculating for what's the assignment. And the assignment is with the Oscars, like the White House Correspondents Dinner, is think about that room and calculate. It's not, you're not at a club where they are there to get a drink and then suddenly you pop up and they're really thrilled.

1:04:23Michelle Obama:They're not, you know, if you go to a high school and they're just losing their mind that you show up, that's a very different crowd than now I'm going to speak to a bunch of, you know, A -list people who don't really like to give it up for anybody. but it's all just a calculation. You got to calculate and then have fun.

1:04:49Craig Robinson:Do you like that risk? Does it feel like, you know, I know how to be, I know, like this is you on some high wire. Do you feel, is it a test for you? I like,

1:04:58Michelle Obama:I think I must like that to some degree because I keep signing up for things like that. And so that's a problem. And when it's three o 'clock in the morning and I can't sleep, Liza's like, maybe we don't do another one of these.

1:05:12Craig Robinson:Do this again? But I do like, I think the trick is to,

1:05:22Michelle Obama:I figured out a long time ago,

1:05:23Craig Robinson:if I'm having a good time, things tend to go well. Yeah.

1:05:28Michelle Obama:It's almost unheard of for me to have a really good time up in front of people. And people afterwards say, well, that was awful. If I'm enjoying myself. So I just keep trying to think of things. I want to tell a joke I really like. Yeah. Now, they may not like it, but if I really like it… You will crack yourself up. I will crack myself up. And then I'm like, okay, well, you know, this job didn't pay much anyway. So, I had a good time. And that's kind of my mission is I want to think of things and do things that I enjoy. And I think instinctively, we like to watch people having fun. We like to watch athletes who are having fun.

1:06:07Michelle Obama:Yeah. You know, they're really like, when they're playing well, they're enjoying themselves. It's fun to play at that level. It's fun to give a great speech. It's fun to be up in front of people doing what you feel you were put here to do. So that part I really like. And it's just doubling down on that. How do I figure out? And if something starts to develop and I think, I don't really like doing this. Cut it. Don't do it.

1:06:37Craig Robinson:Do you feel like comedy is more fraught these days? I mean, it just, you know. Yeah.

1:06:44Michelle Obama:I think it's -

1:06:44Craig Robinson:Talk show hosts or not, you know. Yeah.

1:06:47Michelle Obama:I mean, obviously I'm friends with the other, the hosts. I'm not a late night host anymore, but I'm friends with them. And I think they're all very talented. They're really good people. And they're in a tough situation because of your job is to go out and talk about the news every day. And I was never strictly a comedian that lived off the news or did, I usually tried to find things that were silly and funny outside of the news, but we also had to do the news. And things are so divisive right now. And I think it's gotta be just a really tough task. and I do have empathy for people who are trying to figure out what's funny in this because I know just as a citizen, I get up in the morning and I look at what happened in the news.

1:07:51Michelle Obama:My first instinct, I like to be funny, but my first instinct when I read the news is nothing here gives me joy or is making me laugh that hard and that makes me think of ideas outside of the news about everyday life or something. There's a weird ad on TV that cracks me up. Those are the things that I probably look for. But if you're doing one of those shows, how do you not talk about it?

1:08:22Conan O’Brien:That's right.

1:08:23Michelle Obama:And then how do you not wear your heart on your sleeve and maybe get mad or, you know, so it's difficult. I think it's difficult.

1:08:34Conan O’Brien:On our show, we have an audience question, a listener question. But before we get to the listener question, I need some development. You've been in the podcast business for a long time.

1:08:48Michelle Obama:It feels, well, actually, no, not that long. But yeah, I guess kind of. Longer than IMO. Yes.

1:08:54Conan O’Brien:Okay. Yes. Any tips? Any best practices? What is it about the podcast that you like doing? that might be helpful to a, I won't say young, but fledgling podcaster like myself. You are younger than me. No, I'm older than you.

1:09:12Craig Robinson:Yeah, he's my big brother.

1:09:14Conan O’Brien:Yeah. He's older than us. I'm older than you.

1:09:16Craig Robinson:He's an old man.

1:09:17Conan O’Brien:I was probably on campus when you were on camp. I was probably over in the gym playing your basketball team when you were a freshman. Yeah. Yeah. So I'm older than you are. So you were in the gym

1:09:29Michelle Obama:playing real sports when I was in a - You were at the Lampoon. I was in a weird castle on Mount Auburn Street thinking of something weird and giggling. Yeah, see, and I probably would have preferred to be over there. Yeah, it's me. Yeah. You know, who's the cool one, really? Yeah. Wow, that's incredible. I thought you were maybe 32 years old. Oh, yeah, thanks. And a ventriloquist. Budding. Budding ventriloquist. I'm with you on that. I'm going to help you. I'm going to find you the right dummy. I'm going to get you a good one. I'm going to get you a teacher too because I want to see you do it.

1:10:05Michelle Obama:Please. I think, oh, I mean, I don't know the answer. I know it works for me. Okay. Which is, and you're doing it, great snacks out there. All right. It starts with the snacks. It ends with the snacks. Okay. Don't let this one, too many kale chips. You know, you got to have some good, and then some of them have to be bad for you. You're going to have to be. No kale chips. No kale chips. No high fructose, this or that. But no, you want to have, you've got that. You've got good snacks. There's a really good vibe here. Like it's fun to come here. And I think that's a big thing. You want people to come into the store and want to walk around and check stuff out.

1:10:44Michelle Obama:And so that is all working. And you two know each other so well. You can finish each other's sentences and there's a good bond here. So that's all good. And to me, it's like, I don't, I mean, I think I'd be a fool to give you guys any advice on what to do that you're not doing. I mean, it'd be nice if I got an expensive gift on the way out. I'm just putting it out there. You're working on that. You know, like a watch. Like a good watch. Like a Patek Philippe watch. Here, you can have this one. That watch weighs more than I do. I could drive that watch home. It looks like a car. No, I think, I mean, it's all about enjoying yourself.

1:11:30Michelle Obama:Again, I'll go back to that same thing I said about a word show or doing a nightly show or anything else, which is talk about the things you want to talk about, that you're passionate about. I think passion and authenticity works better than anything in this format. And you're doing it. So I don't, you know, other than stop lying about your age, come clean. You are a 32-year-old man. I am.

1:11:55Conan O’Brien:You were born in 2005. I am 63. We're soon to be 64 in April.

1:12:02Craig Robinson:April.

1:12:02Conan O’Brien:Wow. He's my big brother. April 21st.

1:12:05Michelle Obama:I'm the 18th. I'll be 63 on the 18th. Yeah. I like an April birthday. So do I. I like it. Why? What's so good about it? You get far enough away from the holidays. What's so good about it?

1:12:15Conan O’Brien:You get far enough away from the holidays where when you get gifts, it feels good again.

1:12:19Michelle Obama:Yeah. Also, I grew up on the East Coast. Okay. You guys, I know Midwest. It's starting to get nice. And so I always associated my birthday with, wait a minute, the sun is out for the first time in nine months. And there's a little bit of joy and some birds are chirping. I like that.

1:12:39Craig Robinson:The smell of grass.

1:12:41Michelle Obama:Are you into horoscope stuff? No, I'm not. I'm not at all. I'm not.

1:12:45Craig Robinson:I thought you were going to say that. I'm not. Well, all these young people are, so I probably know more than it because it's all about, oh, you're a Leo rising in a sun moon to sleep. And I'm like, what?

1:12:56Michelle Obama:No, and then I ask them, they'll say things like, oh, that's so Aries. And I'll say, why? And they'll say, oh, because Aries loves a challenge and loves to push themselves and is a ray of light. And then I'll read, well, what's a Taurus? Loves to really challenge themselves, full of goodness and light.

1:13:15Craig Robinson:And then if you say something else, then say, oh, you must be a Cancer moon. And it's like, okay, so now there's something for every aspect. because there's moons and there's your sleeping sign. What are these?

1:13:28Conan O’Brien:There's only 12. It can't be that different. Everybody can't, right? Well, we just alienated your entire staff.

1:13:34Michelle Obama:I know. They're listening right now like these people. They don't get it. And they also like manifesting everything. Well, that's Oprah's fault. We blame Oprah for that. You can manifest it. I can manifest all day and all night that I want to be an amazing basketball player. It's not happening. It's not happening. Or I'd like to be a male model. I'm going to manifest it not happening. There's so many things that I cannot manifest. Right, right.

1:14:01Craig Robinson:Well, let's get to our listener question. Okay, yes. Get some advice. My name is Jake and I'm from Indiana. And my question is, how do I overcome feeling lost in my career? I achieved my childhood dream job at 21. I had worked for it since fifth grade, but then I decided I just didn't like it enough to do it forever. At 25, I switched to a new job with good opportunity, but it's far from home where I'm originally from, and I don't want to be here forever. I'm now 26, and I don't know what I want to do. I don't love the idea of going back to school because I'm not sure there's anything I'd love to study full-time.

1:14:39Craig Robinson:I have ideas, but nothing concrete, and with this constantly evolving world, I feel stuck, lonely, and depressed as a result. Hell. 26, too. This is what we were talking about, right? I know.

1:14:51Michelle Obama:I mean, this has been a big theme of this podcast, not through design, but it just happened. But in the brief description, you listen to what Jake's achieved already and it's really good. And this is just one of the things that takes a long time to figure out. I do think that we're in a world now where you take constant snapshots of your life. And if the latest snapshot doesn't please you, you think things are really dire. And this is called being 26. I mean, it sounds to me like Jake is kind of ahead of the game, has already had a lot of success, has options, and now is wondering what to do. This is a feeling you're going to have now.

1:15:44Michelle Obama:And then it's going to go away and you're going to have a period where you think you're back on track and then it's going to come up again. And this feeling will revisit you. And that doesn't mean there's anything wrong with you. It means you're a person. And we all have that. And it's anyone who looks at you and thinks, well, she doesn't have any problems. She's a former first lady and she's got the world by the tail. And it's just doesn't understand that you can have a really bad Thursday. You can have a really bad October. You can have a bad year. You can have a bad two years. You can, I mean, that is called being here.

1:16:31Michelle Obama:That's what, and no one escapes it. No one gets out of it. And I think young people like Jake put so much pressure on themselves and they forget that But sometimes treading water is just fine. That's, you know, not every day has to be a sprint to the finish line. You can have periods of your life. I've had many of them where I think I'm not really getting anywhere. I'm treading water, but I'm not drowning. So I think try not to be too self-critical. try not to be too tough on yourself and appreciate what you have and what you've already achieved and know that also 26 you're a baby that's my answer

1:17:23Craig Robinson:that's a it's a it's a great answer it's it's spot on and Jake it's like 26 is it's if you're lucky and luck has a lot to do with it But with this generation, they're going to live until their 90s, you know, assuming that we continue to have good health care, which this generation should care about. That's going to play a role. But science is definitely on their side. We've learned a lot. You know, people are healthier. They're living longer. So let's just say if Jake is lucky, he's going to be here until he's 90. Yeah. You know, that's like I can do that. That's 70 more years, 70 more years to live a life and to figure it out.

1:18:11Craig Robinson:So the 20s and the 30s, and I would even say now the 480s, are the period where you aren't going to know. I mean, there are a handful of people, and they're rare, that pick a thing at 18 or 22 and they get it right. It's their passion. They're good at it. And then there's a job. Yeah. Right? Yeah. That's not the norm. You know, that's the exception. And again, with social media, he's probably seeing some of those people post, look at me living my best life at 26. I'm already a millionaire and I've done this and I have a boat. That's not the norm. It wasn't the case for me.

1:18:50Michelle Obama:Also, people don't always tell the truth.

1:18:52Craig Robinson:That's right. On social media. That's absolutely right.

1:18:54Michelle Obama:So that may be someone else's boat.

1:18:56Craig Robinson:Exactly. Nine times out of ten. I've done that.

1:18:59Michelle Obama:I've often taken photos of boats and said, check out my boat. I don't have a boat. That's right. You've often done that? No, I'm kidding. I'm going to start doing it. Because I just, I'm getting in the idea that that'd be cool. Right. But no, I think that's people.

1:19:17Craig Robinson:There are going to be many lives, many, if, you know, and that's what you want out of life.

1:19:22Michelle Obama:Yeah.

1:19:22Craig Robinson:You know, you want to keep evolving. You want to keep trying on new things. And, you know, I certainly did that. I thought I wanted to be a lawyer, went to law school, wrong about that. Didn't like that. That felt a little shocking. All that debt. And I was like, damn, I should have checked to see if I like law before I did it. But I didn't. And so I left the law. And thank God I did because it wasn't the profession for me. Thank God I had parents who didn't care about that. And they encouraged me and my brother. We went down a whole, should have been a certain career path. And entered into it and said, whoa, this isn't me.

1:20:01Craig Robinson:And so I had to redefine it. I had to start looking around, asking questions, exploring, trying on new things. And that's when I learned that I love service. And I actually like working with people. I don't like reading documents and just writing memos. I like sort of living in life. I learned that about myself. And if I had stayed in the law firm and become partner, I would probably figure that out. Because ultimately, you do have to wake up. Even if you pick a thing. I've met people who have been in a profession their entire lives, just putting up with it because it paid the bills. And then at 60 or 70, they find the thing that they care about.

1:20:44Craig Robinson:The work is waiting for you. That work of figuring yourself out, it's waiting for you.

1:20:50Michelle Obama:He's probably in it right now. He's in it right now. A guy like Jake, you're not even aware. are. Some people think, sometimes I'll talk to one of my kids and they'll say, oh, I wasted time today. I've got this thing, but I didn't really, I didn't make a lot of progress on it today. And I'll say, I have found that often you're working and you're figuring things out when you don't even think you are. Because we have, you know, front part of our brain, we have all these, and then you have a part of your brain that's chewing on things while you don't even know it. So Jake might be figuring a lot of stuff out right now That's crucial Where he realizes I want to be an astronomer But that's still a year from now When he has that revelation But it is working on him On some level

1:21:40Conan O’Brien:It's funny you say that, Conan Because I was just watching something And I can't remember if it was PBS Or it could have been on social media But Neil deGrasse Tyson the renowned scientist who is very entertaining, but I really enjoy him. When he talks, I listen. And he said something that I had never heard before, that procrastinators are usually highly intelligent. Yeah. For the reason you said, that they procrastinate because they want to give their brain enough time to come up with the solution. And like you said, this could be happening with Jake right now.

1:22:26Craig Robinson:Oh, yeah. Yeah. I think that's true.

1:22:29Conan O’Brien:So hang in there, Jake. And, you know, my sister and I talk about this all the time. Try stuff. Try stuff to find your passion. And sometimes you don't find your passion, but you'll find something that's pretty interesting. Yeah. And there's no,

1:22:45Michelle Obama:I think a lot of young people don't realize that they have more room for error than they think they do. You can try something and wipe out or it just doesn't go anywhere. No one's paying that much attention and no one later on is going to present you with, hey, wait a minute. I know you're a big success now, but remember when you tried to open that dry cleaning business and it didn't work 35 years ago or whatever. But no, that happened. I got out of it. I paid my debts. and then I tried this. Once you figure out what it is, you're not penalized. No one, there's not a referee there watching, blowing the whistle, saying, nope, you're out.

1:23:26Michelle Obama:You just made a mistake. Yeah. Life's over. It feels that way, but it's not happening. Yeah. Yeah.

1:23:31Conan O’Brien:That's a great point.

1:23:32Craig Robinson:Well, speaking of evolving, and hopefully that helps Jake, you're still evolving. I mean, did you just have your acting debut? Yeah, I did. I mean, I watched, if I had legs, I'd kick you. It was, It's intense. It's intense, but so good.

1:23:50Michelle Obama:She's, I mean, Rose Byrne is phenomenal.

1:23:54Craig Robinson:She is amazing.

1:23:55Michelle Obama:Yeah, she's absolutely spectacular. And so, yeah.

1:24:00Craig Robinson:How was that for you? I mean, was that your first time? More or less. And you were serious. Yeah, it was a serious role.

1:24:07Michelle Obama:They sent me the script and I said, well, this is a great script, but this isn't really what I do. This guy's the complete opposite of me. The director met with me, Mary Bronstein, who wrote it, directed it. And she said, I really want you to do this. And I said, I don't think you should want me. You should get someone who really knows what to do with this. And she said, I really do think it's you. And I said, okay, I'm going to try, but I give you permission to fire me at any point and we'll still be friends. And I said, if I'm not, because I love Rose Byrne, I don't want to let her down. I don't want to get in the way of this amazing movie.

1:24:50Michelle Obama:Fire me, fire me, fire me. And even if you shoot with me and you want to cut me out, cut me out. No hard feelings. But again, I worked on it. I thought about it a lot. I worked on it. You were good.

1:25:05Craig Robinson:You were incredibly believable. There was no sign of regular Coen.

1:25:10Michelle Obama:Well, here's the disturbing part. The guy I play has no empathy. Everyone hates him and wants to kick him. And people were just so mad at my character. And it's worrying me that that's inside. I may have let out the real me. Yeah. And this, you know, that's in there. And so, but it was a real challenge, and it was scary. But again, going back to, you know, the question we just got, I've gotten to a point in my life where I think, give it a shot. There are things I know I shouldn't be doing. If someone said, hey, fly this F-16 fighter, gee, I've never done it before, but no one's going to penalize me if it doesn't work out.

1:25:55Michelle Obama:Yeah, you'll be killed. You might kill other people. I know there are a lot of things I shouldn't just give a try to, but this one, I really went off the belief of the director. And it was a lot of fun. And I'm really proud of Rose is because she's nominated for Best Actress.

1:26:11Craig Robinson:I know. She's phenomenal. You've got to. Craig is not pop culture ready. I told him he has to be better in this job where pop culture is. That is not true. He's got to watch movies.

1:26:24Michelle Obama:What do you watch?

1:26:27Conan O’Brien:Turner Classic movies.

1:26:29Michelle Obama:Oh, okay. All right.

1:26:30Conan O’Brien:I watch Turner Classic movies. Snore.

1:26:36Conan O’Brien:I like watching movies. It's hard to watch these new series that have part after part after part. I just, you can't keep up. And then, you know, I've got a job. I work for the Coaches Association. I'm coaching my kids' teams and I'm doing this podcast. I don't have time for just, you know, real wife, real housewives of Brooklyn. I don't have time. Is there a Brooklyn housewife?

1:27:02Craig Robinson:Yeah, there is. There is not. It's New York. It's not Brooklyn.

1:27:06Conan O’Brien:Oh, well, I bet they all know. This is what I'm dealing with. I bet they all live in Brooklyn.

1:27:09Craig Robinson:No, they don't. There's a real housewife in Staten Island.

1:27:11Michelle Obama:You should check that out. Is there really? No, I just made it up.

1:27:15Conan O’Brien:Do you have to recuse yourself

1:27:17Michelle Obama:when the... No, because I really have no power in this thing. Oh, okay. I'm like the cruise director on the boat. I'm not the captain. I don't steer it. My job is to get everyone to play a little shuffleboard, get them drunk, and then, you know, hope that we don't hit anything. But that is my job. So, no, I don't have to recuse myself. I'm allowed to be really excited should things work out for Rose. But if not, you know, she still gave an amazing performance. Yeah.

1:27:41Craig Robinson:Well, it's been great having you. This has been lovely. Thank you, Conan. Thank you so much. Well, it's a joy,

1:27:48Michelle Obama:honor to talk to you both. Likewise.

1:27:51Craig Robinson:And it's always a joy. Really, really. It's a good time.

1:27:54Conan O’Brien:It's great to get to know you more. Thank you for doing this. So you and I are going to be hanging out a lot now, Craig? Anytime you want to hang.

1:28:00Michelle Obama:I don't think that's true.

1:28:02Conan O’Brien:Yeah. I think I'm going to start cold calling him.

1:28:04Michelle Obama:It's true for you.

1:28:06Conan O’Brien:So here's the thing. When I come to L.A. Greg, it's Conan. Let's hang. Let's hang. Let's shoot some hoops. That's right.

1:28:14Michelle Obama:I'm going to drain some threes from 80 yards away. They don't go anywhere near the bucket.

1:28:20Conan O’Brien:Nowhere near.

1:28:21Craig Robinson:I tell you, that's the bit.

1:28:22Conan O’Brien:And then I'll go to the back alley comedy club with you. I think you would do better. With ventriloquists. You would do better at comedy than I would at basketball.

1:28:33Michelle Obama:That I promise you. Would you?

1:28:34Craig Robinson:Would you teach him how to do ventriloquism?

1:28:38Michelle Obama:I don't do ventriloquism, but I will get a person to teach you ventriloquism, but we have to get you the right dummy, too. It's got to be a good dummy.

1:28:51Michelle Obama:No way. Surprise for both of them.

1:28:54Craig Robinson:Why don't you do the honors? Do the honors. Look at this.

1:29:00Conan O’Brien:Oh, my goodness. You guys are too much.

1:29:03Craig Robinson:Can I just say? Do you see? This is beautiful and horrifying.

1:29:07Michelle Obama:At the same time, this dummy has had very bad work done.

1:29:13Craig Robinson:Look at his hands. His hands are huge.

1:29:17Michelle Obama:Yeah, this is the nightmare that will never end for me. I'm probably, I'm going to be trying to do the Oscars and I'll stop because this face will be looking at me. Did you see if we were there in the front row? Put him in the front row. We'll put him right next to Timothee Chalamet. Yeah, yeah. Hey, Conan! You having fun up there? Get some better material, Conan! He's gonna steal the show at the Oscars.

1:29:46Conan O’Brien:You know, this is a really tall dummy.

1:29:49Craig Robinson:It is. Well, it should go on your lap. It's on my lap. Oh, okay. Well, he's a basketball player. I get it. This is perfect. He's a basketball player.

1:29:59Conan O’Brien:This is perfect.

1:30:22Craig Robinson:Do you ever find yourself scrolling through headlines, especially health headlines, and just thinking that can't be true? Well, I certainly do. 2025 brought us some ridiculous far-fetched health claims and some especially terrifying changes in public health. What's in store for us in 2026? I'm Chelsea Clinton, and we're back with season two of my podcast, That Can't Be True. Follow along and catch up on season one wherever you get your podcasts.