The Three Questions with Andy Richter - Jon Lovett

Episode Date: April 16, 2024

Comedian and writer Jon Lovett, host of “Pod Save America” and “Lovett or Leave It,” joins Andy Richter to discuss balancing comedy and politics, playing Mario on prom night, writing speeches for President Barack Obama, why Jon believes “Late Night with Conan O’Brien” was inherently progressive, some of Jon and Andy’s favorite dad aphorisms, leaving the White House for Hollywood, and more.

Hello, everybody. Welcome back to The Three Questions. I am the host of The Three Questions, Andy Richter. And this week, I am talking to podcaster, comedian, former White House speechwriter, that's my first time talking to one of those, and now author, John Lovett. You know him as the host of Pod Save America and Love It or Leave It. As a speechwriter, he worked for President Barack Obama, as well as for Hillary Clinton when she was a U.S. senator and a 2008 presidential candidate. His book, Democracy or Else, How to Save America in 10 Easy Steps, is out this June. Get your tickets for John's many live dates at crooked.com slash events. Here is my really fun and really interesting conversation with John Lovett.

Well, thank you for coming. Thanks for having me. Are you just plugging your... Plugging the book. The book. Plugging the tour. Yeah. And then plugging plugging your... Plugging the book. The book. Plugging the tour. Yeah. And then plugging Vote Save America. And the pods. And the book is

Democracy or Else, How to Save America in 10 Easy Steps. That's right. Were there 12 or 13 and you're just like, no, 10. It's got to be 10. I'll tell you something. There were nine. Ah, you had to think of another one. And we were really stuck for a while. Wow. And then we figured out a tenth which was hey take a break

breathe yeah breathe yeah self-care just breathe absolutely if that was a real problem we had honestly months right because you can't have nine steps no and you can't have 11 or 12 yeah you want we. You want, you know, if you're at eight, okay, but we are at nine. And also the German language has ruined the word nine. Right. Nine! Right, it sounds like you're desperate pleading for something to stop. Yes, yes.

And then you're going on tour with the podcast, right? With Love It or Leave It. Yes, Love It or Leave It is hitting the road. We're going to a bunch of cities. With Love It or Leave It. Yes. Love It or Leave It is hitting the road. We're going to a bunch of cities.

We have a couple shows in April in D.C. and Austin, and then in June and after we'll be across the country. Nice. Now, do you think of yourself as a comedian who got into politics or a politics person who kind of branched out into comedy? Or is this something you talk about to your therapist? 100%. But we've worked through it, so it's something you talk about to your therapist and i 100 but we've worked through it so it's a good timing oh good no so when i first i always really liked comedy i really liked politics i actually really liked math those were the three directions i felt pulled in and when i first went into politics i had done some stand-up after college in a very amateur way.

But when people find out in D.C. that you maybe know some way to write a joke, you have some sense of what a joke is, it's like being a painter. You show up sober, they make you a foreman. And so it's really one of the most boomerish comments that you'll hear that I'll ever make. But I like it. I like it. My favorite of those is pay peanuts, get monkeys. Hey, pretty good.

Yeah, yeah, yeah. That's one of my grandfather used to say that. Here, ask me how many people work at Team Coco. How many people work at Team Coco? About half. Welcome to the dad talk. But so I ended up writing jokes for Hillary Clinton very early on, even before I was a speechwriter for her. And it was a very big deal to me because I was on these calls with these speechwriters that had been professionals. Al Franken actually had gotten on that call to kind of pitch jokes.

And I remember I made Al Franken laugh. It was a really big deal to me. Yeah, yeah. With a joke about Rick Lazio working in a deli. Rick Lazio having been Hillary's former competitor for the Senate seat. But I remember thinking to myself, John, don't let your head get too big. You're funny enough to be a funny professional, but you're not funny enough to be professionally funny.

That was always what I felt, that I was good at several things, but you're not funny enough to be professionally funny. That that was always what I felt, that I was good at several things, but not great at any one of them. That I was a pretty good speechwriter. I could write some pretty good jokes, but I was never going to be the, I was never going to really be able to turn that into being a true comedian. And then after a few years of being in politics, I had said that to one of my closest friends. And as I was thinking about moving to LA to try to actually focus on comedy, I reminded him of my imposition, like, tell me if my head gets too big because I think I'm about to try to be professionally funny. And I remember him saying, like, I never really believed that. I actually

always thought you could be professionally funny. And so I took a chance. But I've always felt uncomfortable calling myself a comedian. I felt uncomfortable calling myself a writer. I think a lot of comedians feel this way, but I just feel like because, yes, like, of course,

that would describe what I do. Every week, I do jokes in front of a live audience all across the country. Yes, exactly. But somehow, because I didn't get there the normal path, I feel like I didn't do my time to earn the name.

I think that's just a natural thing. Because I sit here and I think, well, the proof is in the pudding. There's another dad statement. You know, you get, like you said, you get paid to be funny. You're on stage entertaining people, you know, whether it's with a, you know, sort of a chat show format or just on your own telling jokes and great. Well, you know what? That's the, that's the final boost I needed. It's done.

Lock it in. No, but, but I, I mean, I also understand it's easy for me to say that about you. And it's easy for people to say that about me who sometimes I'm like, well, what have I really done, though? I mean, I sat on a couch and just kind of. But, man, you made that look easy. You made it look easy. But it's like, I know, but it's, I think that we tend to discount the things that we have a facility for. discount the things that we have a facility for you know like if it's kind of like and i don't give myself credit for things unless it's like i'm sweating and it's a struggle and i really you

know for sure you know you don't want to belong to any club that would have you as a member kind of yeah i feel that i feel that yeah yeah so and and did you grow up in a very political household not really i mean it wasn't like a combo of funny and political? No, it wasn't particularly political. It was a... I grew up on Long Island, Jewish parents, my father ran a box factory,

my mother had worked at department stores and then became a homemaker, and it was... Politics was not a big part of our lives. It was much more about you do well in school, you got to go to a good college. It was about, it was the kind of ambition and drive of that kind of, of that Jewish immigrant mentality. And was there a push for you to be a quote unquote professional of some kind? Yes and no.

To my parents' credit. So my father, so my father took over a box factory for his father. Right. And he didn't expect you to take over the box factory? Well, he saw I couldn't do it.

I didn't have what it took. I couldn't fold the boxes. I couldn't figure it out. Really? No, I made a mess of them. No, he... Because I'm disappointed in you already, you know, by proxy. It was like Lucy with the chocolates.

Yeah, yeah. You were shoving the boxes in your mouth as fast as you could. Yeah, I was hiding boxes. I embezzled. I don't even know how to do that. I was terrible at it. No, I think that he had felt like growing up, he was expected to do a certain thing, that he was going to take over the business for his father. And it was very important to my

parents as a result that they were very supportive and they really wanted me to do well and they really cared about that. But sort of whatever I wanted to do, they were very supportive of me getting to choose what direction I would go. Yeah, yeah. That's nice. Yeah. And did your mom work? I don't have that information. She worked at a department store. She was a buyer for, I believe, A&S department stores, and then she was a homemaker.

Okay. And what was your household like? I mean, was it a big family? It was me and my sister and my parents. It was not a big family. It was very much, it was that love is, you know, it's a very kind of,

you know, dating profile thing these days about the love languages. You know, there's, it's a very kind of, you know, dating profile thing these days, but the love languages, you know, there's acts of service and physical touch and, and gifts. This was a quality time, you know, we were going to go to Little League. We always were together, but it wasn't like a, it was sort of an old school, not very effusive. Right. Right. Like love is shown through acts of an old school, not very effusive. Right. Right. Like love is shown through acts. Yes.

Of taking you places, caring, making sure things are where they need to be, making sure you're taken care of. But not sharing deep feelings. No. Yeah. No. There was not that much of that. And well, actually, so my great grandparents met at a school for the deaf. Wow.

One of the first or maybe one of the only schools for the deaf. And so they were both deaf. And this was from long before there was preschool or anything like that. So their son, my grandfather, didn't learn to speak until he was a little bit older. Wow. So he was always kind of taciturn.

He was not someone who did a lot of talking. Yeah. Wasn't an effusive person. His son, my father, grew up in a household. With a guy that learned to talk late. Right. And so you see how like you kind of can start at two people meeting at a school for the deaf like a hundred years ago. All the way down. Yeah. To not being able to share your feelings in a long car ride. Wow. That's amazing. Well, did, I mean, was that a problem when you were young?

I mean, did you feel like, they don't understand me? No, no, no. They're very, it's more, I think that I was a bit of an outlier in my family. I think my sister is a bit more like my parents and I love my parents and I love my sister, but I was always a bit of a careening, chaotic, emotional part of the family. And they're, I think, a bit more even keeled. And so I think that figuring out that I, that like being enthusiastic and being passionate

was going to be a big part of how I figured out what I was good at was something I had to kind of learn. Because that wasn't, there was a much more kind of, I think, nuts and bolts. You get good grades, you find good college, you think about the career that's going to be best for you. You know, it's a pragmatic, there's a pragmatic kind of safety of that way of thinking. And I thought like that for a long time. And I don't think there's anything wrong with thinking that way.

But I got to a point where I was like, you know what? No, like I, I want to take some big swings. You know, I want to do speech writing or I want to do comedy or I want to move to LA. And I always decided that I would bet on those passions rather than I think the kind of more stable, go to law school, go into advertising, go into finance or something like that. And that's just something you think you were born with. finance or something like that. And that's just something you think you were born with. Yeah. Yes. Yeah, I do. I, I think that I've always, there's the, I think that I've always just had, it's funny because on the opposite, yes, I'm afraid to call myself a comedian, but also I am not somebody who does a lot of worst case scenarios. Like I kind of bet on the right,

bet on things working out. Yeah. Like when I moved to LA, like it, somebody has like, well, what was going to happen if that show didn't happen? I was like, honestly, bet on the right bet on things working out like when I moved to LA somebody asked me well what was going to happen if that show didn't happen I was like honestly you're the first person I never thought about it I really didn't I really didn't

not that I wasn't afraid I truly just when I imagine what's going to happen I imagine the best case and I head towards that and I've been lucky enough in a few moments

I've had look shit hit the fan but And I've been lucky enough in a few moments. I've had, look, shit hit the fan, but like I've been lucky enough that enough times I've gotten the thing that I hoped would happen, that I've been able to string together a life without the worst case scenario laying me too low. I think there's an efficiency to that. And it's like, it's something I've talked about on this podcast before that I've done lots and lots of therapy. And one of the things that you learn, you know, that you learn is you kind of learn the lingo and learn how it all works. You think, oh, I shouldn't compartmentalize, you know, like I, my life should be this sort of integrated sort of free flowing river of awareness.

Then it's like, no, no, the compartmentalizing is great because you embark on a new adventure and what happened you know what happens if it doesn't work out no no that fuck that yeah that goes in a box right you know and and it's much more efficient to to look at well you know we'll cross that bridge when we come to it and and somebody in my life used to always look at the worst case scenario and say, it helps me that in case that happens, I have prepared myself for it. And I was always like, that seems like A, a drag, and B, kind of a waste of time. A friend and I, we have this, we sometimes will rate people. And we'll rate them on two qualities that often get combined, but are different, which is how anxious are they and how optimistic they are. And those get combined a lot, but if you actually think about the friends

in your life, you'll realize, wait a second, they're extremely anxious and optimistic. And I think sometimes people get themselves into trouble when they're extremely anxious and optimistic, right? And I think sometimes people get themselves into trouble when they're both very anxious and pessimistic. I don't think there's anything wrong with kind of going hard, trying for something, believing it will work out, but having in the back of your mind a voice saying,

uh-oh, things might go the other way. And I think there are people that kind of don't expect great things to happen, but they're pretty sanguine about it. Yeah. Right? I think it's that you'll stop yourself if you're both anxious and pessimistic. Yeah, yeah.

I think that's sort of like the trap. Right. Well, I think also, too, and I don't know what to do with this, but I often think, especially, you know, in a podcast where I talk to people who have achieved something. where I talk to people who have achieved something. It's why they're here promoting things and being on podcasts and they're interesting. And there's times when I think like, well, you know, the world is mostly made up of people who aren't striving and what do you do about it?

That is the problem, right? There's a famous example of that, which is, you know, when the planes would come back from their bombing runs in World War II, only a certain segment of the planes would come back and then they would look at the planes that come back and they'd say, well, where are the holes in those planes?

They'd say, oh, you've got to strengthen those areas. And it was like, no, no, no. Those are the ones that came back. Strengthen everywhere else. Because the ones that came back survived. We don't need to strengthen those areas. This is where you could take the bullets. Right.

And so like, you know, we're planes that, if you've had success in this town, in entertainment, in any field where a bunch of people, any field that something that a kid might say they want to do it when they grow up, you know, you've had success in that kind of a field. Like you've made a bombing run and you've made it back with bullet holes, but there are a lot of people that don't get to make it. It takes a crazy amount of luck. And your experiences are not necessarily helpful to people that are experiencing different kinds of setbacks. Yeah. Were you like a leader in high school? No. Were you like, no?

I think I always wanted to be. I think, you know, you imagine, you know, you're watching West Wing or something and you imagine a movie. But I was, what I think about now is, oh, of course, I was, first of all, I was closeted. I'm gay, I don't know. What?

Yeah. Oh, I was closeted. I'm gay, I don't know. What? Yeah. Oh, I know. Well, my research says that you're a real cocksman with the ladies. Wikipedia. A cocksman. There was a time when my Wikipedia only said, love it is gay. Which I was like, okay. Okay, yeah. It okay it's not wrong it's false it covers a lot of stuff curious about the person that edited that in there sort of sitting in their home doing

free work for this website being like i think people need to know this guy's this guy this guy's seen penises that aren't his own this guy i think this guy knows a way yeah a coxman of a different sort he's for the fellas for the fellas a confirmed bachelor but uh uh no i think that i was depressed and i was closeted and i was afraid to be myself and i think i spent a long time being that way and really it's i there's um there are these these studies that come out that say wow like even even in places as progressive as New York or Seattle, that gay people still have higher rates of depression. And all kinds of members of the LGBT community still have all these different risks of self-harm. And it's like, yeah, moving to New York doesn't solve everything.

And you're dealing with thousands of years of built-up cultural biases. And so, yeah, I've come out and I've come very happy, but it took me a really long time. It's not about the little bullying moments. It's not about the fear of coming out. For me, it wasn't those things.

I think it is more the internalized, completely unacknowledged, unexamined homophobia that you kind of... And homophobia, not just about being afraid to be gay, but the homophobia of being afraid to be feminine, to be emotionally and psychologically open and willing to try things and willing to kind of not be what you thought a boy was supposed to be, whatever that means. So I think I spent a really long time grappling with that.

And truly, I think it's like an ongoing project. Like I think even now, I think about like, it's what I wear, how I present, how I'm talking to you now. Like what version of my voice are you getting? Even in this sentence,

it's getting gayer because I'm realizing I was doing my serious podcast voice. And it's like, well, I don't want to do that. I want to gay it up. I want to really fag it up here with my friend. Do it, do it,

man. Let's do it. Do it, man. Do it, man. Come on, man. Nothing has ever, look, the most comforting words for a gay person are, just do it, man. Can't you tell my love's a crow? I have a gay son and i think i think that even with him like part of his i mean i i can't speak for him but i think that they're like even in his sort of you know coming of age and he was he was really kind of never closeted at least not with his mother and me but i think like there's also

in addition to figuring out being a man in the society what a boy is and what a man is it's like also like what gay is i think you know it's like like you got to figure out that out because you know my dad is also gay um i'm surrounded by him skips the generation yeah you know it really does because i am 100 hetero ladies um but i think it was a you know it was like he's kind of 50s gay like they're still like they're still i think the closet haunts him in many ways. Yeah. Well, I also, so much of what it meant to be gay was to be gay in defiance of sometimes explicit laws. Sure.

But also a ton of biases and rules for what's acceptable, what's not acceptable, rules about what could get you fired, what have you. rules about what could get you fired, what have you. And so much of gay culture was about defying that. So much of what a pride parade is was about defying that. And I do think like it is, we're still in it. I think that I was coming out and I think even still today, though to a lesser extent, we're still in this kind of space between where there is a ton of acceptance, a ton of acceptance. And easier today than it was for me, easier for me than it

was for anyone before. But the like legacy and assumptions and like kind of the cultural divot of so much homophobia is still there. And so being a gay kid today, what a blessing when you can look all the way back. But at the same time, you're now in this place where so much of what gay culture is and has been is a culture of defiance, but that doesn't necessarily speak to you because that's not your experience. So how do you figure out what it means to be gay when so much of the culture that you're going to look to because your parents aren't probably aren't gay um they still have some questions about you but most gay kids don't have some don't have a mincing sweet boy

i'm just fancy sir yeah sure i am merely fancy It's a beautiful blouse you're wearing, by the way. Thank you very much. But you have to figure out what it means for you. And it's still hard. It's just still hard. Well, it's, you know, it's, I mean, and we'll get to it later. Because, you know, because like one of, you know, like you wrote the don't ask, don't tell speech, you know. And we'll get to that later.

But it's as you said, we're dealing with thousands of years, and it seems like, oh, the world's really pretty cool now in comparison. But it's been five minutes. I also think that's right. Barack Obama said, I'm for civil unions. I'm not for gay marriage. And we all knew he doesn't. He's fine with gay marriage. When I was a speechwriter, I remember when a Democrat saying, I'm for civil unions was an applause line.

Yeah. Because it was an implicit rejection of the efforts to ban all kinds of gay partnerships and the terrible homophobia on the right. And within a few years, when a Democrat said, we must have civil unions, applause, applause, applause, applause starts getting quieter, applause starts getting quieter until it was sort of like a, yeah. And then it was like, nope, it's time to be for marriage. It happened in like four years. I do think though, sucks but yeah that process

and that's like you know people would get very impatient and they get very impatient with their democratic leaders yeah because they want things that are gonna eventually get there they wanted to get there now but the fact is they're governing for everybody and half the people don't want that and yeah it takes a while. You got to wear them down. And that was like when he said, I'm more in favor of civil unions, people scream and yell,

but it's like, yeah, but the guy, it's coming, he's got to say that or else their hair will set on fire and it'll be a distraction from a million other things. And I do think that there's an outside game and an inside game. You need people on the outside pushing for the right thing. Not the right thing that's totally convenient, not the right thing that 51% of the country will get behind. You need people outside pushing on the right thing.

You also need people inside, some of whom say, you know what? I'm not just going to build a policy platform that has a set of 55, 45 and 65, 35 issues. I'm going to do a bunch of that. But you know what? On this one, this is too important to me. I know that voters aren't with me yet, but I'm going to do my job to persuade them. That's part of what my job is. And I think you can see that at every level of government, but when you're the president or when you're running for president, when the stakes are so high, especially now when the stakes are total, I do think- Nuts high.

Right. Just nuts high. That your goal, right, is to do the most good. If you view your path to winning as requiring you to focus on issues A, B, C, D, E, F, and G and not issue K, that might be something that's important. It might even be something you work K. Yeah. That might be something that's important. It might even be something you work towards if you win, but not something that's going to be persuasive. Sometimes politics is politics.

And you're going to say, you know what? This may make some people upset. And by the way, I agree with them. But for right now, I don't want to talk about that issue. Yeah. And depending on the issue, depending on the day, depending on the campaign, that might be something you understand,

or that might be something you think is kind of ugly in politics that it's worse. And I don't know. Maybe both things are true. Yeah. Yeah. No. And I mean, and as I just said what I said, like I know how frustrating incrementalism can be, but it is kind of like it's a fact of life, not just in politics, but, you know, when you think about just, think about just my development as a human being, it's incremental. And it isn't to say too that people should not be pushed and pushed and pushed and thank God for the people that really, really push. Politics is in so many ways,

so completely broken. And especially when one side has this, you know, there is this, when one side says, if we lose the game, we're burning down the stadium. It's hard to, it's hard to play. It's hard to play. But despite all these, despite all the ways in which it doesn't, the system feels completely broken, there's still persuasion that still can work, right? Like you look at what's happening just in response to Roe being overturned. There was a special election in Alabama where a seat just got flipped. Why?

Well, because voters in Alabama said, you know what? We didn't like that our Supreme Court ruled in a way that might make it impossible for me to have a child through IVF. You've seen that through special elections all across the country where people even in very red places are saying,

you know what? I know that for years polling on this might not have made this clear. And I know that this is a controversial issue. And I know that there are people in my life that feel differently. But I'm going to go vote because I believe even if I personally and a lot of people do have concerns about or moral questions and discomforts with abortion, because that is what a lot of people feel, have concerns about or moral questions and discomforts with abortion, because that is what a lot of people feel, I'm going to get in my car and I'm going to drive across town and I'm going to vote in this special election because

I want abortion to be protected. Yeah. And because that engages people where, you know, trade does not, you know, they don't even, people don't even know, you know, they don't even know. It affects them. And they have their own lives, you know, their lives are busy. But if they say IVF, what? Fuck that.

That's crazy. Crazy. Got to put an end to this, you know. And it was like, and didn't Trump won that district by 20 or something? Something like that, yeah. Something like that. So, you know, thank God is all I can say. Thank God. Well, let's get back to you oh

about the world oh um you went to college at williams college where is that it's in northwest massachusetts in northwest massachusetts and why there i don't know i think i made a weird move on i made a weird decision i think i made a weird decision i i was a closeted uh nerdy five foot seven gay kid who went to a sports college in rural massachusetts i don't think i was i don't think i was so hot i don't think i was making pristine decisions but i ended up loving it but at the but why did I go there? I don't know. Sports college. Why am I living with lacrosse players? What is this choice that I've made? I could have gone anywhere. We don't sleep in beds. We sleep in foot lockers full of footballs.

That's right. Is it like a liberal arts college? It's a really great liberal arts college. It's a great math program. It's a great school. And I loved Williams. And you studied math? I did. Wow. Yeah. But you never decided of the triumvirate of interests. Here was the problem, which we have math, politics, and comedy.

The problem for me, so there was a kid I went to school with. He actually majored in physics and became, I believe, yeah, he did become a physicist and he could do a Rubik's Cube behind his back. Oh my God. And I just remember thinking.

How the fuck he would picture it? He would do it, look once, and do it again. Oh wow. And I remember when I saw that, I thought,

John, you are ambitious. You are not good enough at math to get the life you want out of math. You may be, you may make the funniest PowerPoint at the senior seminar presentations, which I did.

But no, you're not going to, you're not going to knock anybody's socks off with your math skills. In fact, I did a presentation on statistics once. And the joke at that event was that I had bound and gagged the statistics professor so that it couldn't be properly evaluated because he missed it. Because nobody believed that they were like, we need a stats guy here. We don't have one. And we're pretty suspicious of you. It's funny. It was a funny presentation, but we don't know about this math. But no, but I loved math.

And I ended up, after I graduated, writing a paper with my professor and publishing a math article, like really kind of pursuing it. And I just realized that as much as I enjoyed it, it wasn't going to be the fulfilling career I wanted. So I still love like hard math problems. I love thinking about math. It's sort of a hobby. But it does not, it was,

it was, it was never going to be the full-time career. Yeah. I don't think. It's pretty much the only difference between you and me

is the math thing. Yeah. Because, ugh. Yeah. Because it's, because, you know,

because you're always saying like, ah, the only thing that I hate more than not having a cock to suck is math. As a Long Island Jewish guy, I really, if it weren't for cocks, I'd be mad at math still. Oh, God, what have we done? Can't you tell my love's a crow? Well now, it says that you gave the speech the graduation speech

Yes Was the rest of the class in on that? Yes, I ran for it. It was an elective office. I ran for class speaker. I had this idea. It was such a Tracy Flick thing, but I was so unpopular when I graduated from high school. And when I got to college, I was like, you know what?

You're going to make friends here. You're going to be friends. You're going to make friends here. You're going to be friends. You're going to make friends here. Whether they want to or not. Whether they want to. You're going to football guys. You're going to think you're okay. And they're going to find some nerds.

You're going to make them your friends. You're going to fucking look good. But I decided that when I was a senior, I was like, you know what? I'm going to run for class speaker. That is a fucking popularity contest. I want to win a popularity contest. I'll show those kids from Syosset. And so I was like, I'm going to run for this thing

and I'm going to run for class speaker. And I did. And it ended up becoming, it was like a real campaign. I remember I was running against a football player and then it became like the jocks versus the non-jocks. And there was like, oh, who's the female, the field hockey team going to vote for? But I won.

But I won that race. It was a very big moment for me. Nerds rule. And I, hey, nerds rule. Now, we don't go back and watch those Revenge of the Nerds movies because we won't like what we find. But in theory, if we close our eyes and don't picture anything. They're very empowering. Yes. Look, we want the nerds. As our eyes and don't picture anything. Right. In theory.

They're very empowering. Yes. Look, we want the nerds. As long as you don't watch them. Don't do, and simply do not watch them. It's very important that you don't watch them. But just believe. Just believe in the idea of them.

Don't turn them on. Oh, dear. of them don't don't turn them on oh dear but uh no and i spoke at that graduation and i got some laughs and i was like you know what i'm this is i want to give this you like that i liked it i liked it and i thought i can do this i can do this um and so i i moved to new york and i by day would be a i was a temp paralegal filling out forms at asbestos law firms, helping people get their money. Woo, party. Yeah, it was a blast. It was just a windowless room, and there was an inbox and an outbox, and real paralegals all day would fill up the inbox.

And our goal was to get the process, that paperwork, into the outbox fast enough before they could bring us another stack so that we could chill. Wow. Day after day. And it was maddening because we have absolutely no insight into some days, three or four pop in. It's pretty chill. You're getting paid to talk about movies. And then some days so many people are filing asbestos claims and it's, we have no idea when they're going to happen. It was maddening. And the room was truly windowless. Wow. Truly windowless room. Door opens, files come in, door closes.

Door opens, files go out, door closes. And we just did that day after day after day. But at night, I would do open mics or I would fill out law school applications just to keep my – Or stop evildoers. Right. For sure. For sure. Get my underwear on and

kill them with kindness at what point did you come out if i may ask i started coming out right when i got to college right right before maybe like that very end of high school so by the time you you graduated yeah i'm out and about you were fully out yeah yeah for sure and was it was it well received at home yes yeah it was it was yeah my it was it was a very home? Yes, it was. It was, it was, it was a very, I think that it was, everyone was very supportive of me. I think it took a beat for them to understand how it could be true because in fairness to them,

they were like, have you ever had a girlfriend? No. Have you ever had a boyfriend? No. Interesting. Interesting. So it was a bit more like, how do you know you fucking virgin?

You know, that kind of a thing. They didn't say it exactly. You should do a Pepsi challenge. Blind test. Yeah, for sure. I think that's either RC Cola or I think it's either RC Kohler. I think it's a penis. I do not like this.

That's a vagina. Is that a tab? Oh, ick. No, thank you. Is that a tab? No, it's a vagina. It's a vagina. Oh, yeah, it's fun. I's a vagina oh yeah it's fun

I mean it's it is fun like parents that it's just it's funny to like not to like be like

are you sure well just they were from it it was really just like I think they hadn't thought about it they hadn't thought about it so but it was all

they were very supportive all my friends were supportive it was really I got a lot of the yeah yeah of course you are right right come on you freak cake are you kidding are you kidding at one point when we've seen you walk when my son was my son has had my son and his boyfriend have been together for like six or seven years they they started dating when they were like 16 and at one point my daughter who's five years younger than him i i guess my son was hanging out with some girl uh you know like had a friend that was

a girl and my my daughter at dinner said she said like i think will has a girlfriend and will will just like he rolled his eyes he's like yeah surprise. Just the gayest answer you could possibly have. Surprise. How nice to be a, like, to have a, to be able to date when you're that age. I do think like so many people my age. It's LA. But they just, you pay for that lack of, you pay for not having had that time for so long and i mean i do think that a lot of like gay people end up with this sort of prolonged adolescence in part because they just never got

to have that formative experience absolutely absolutely i mean when i like my son's prom pictures to show them to people at work and to the gay members of the conan staff you can show the straight people too though they might want to say you know just i was terribly ashamed their eyes bleed no no he went he went to prom with a boy uh no i would but you know i'd show them around you know i would show them to everybody but but i could tell like you know like these 58 year old gay men are like oh that's so sweet but you could also it's like you know like also a punch in the gut you know kind of a little well just a little jab you know like damn it i this i never had never had i played mario 64 during my prom did you i did oh wow so my date was luigi oh but you weren't

at the prom right no no okay because i was gonna say that would be distract. I was at home with Luigi Me and Luigi at Sammy. Oh, what do you mean your brother's here? Oh That's a threesome That's not the right pipe Mario I don't know why I came in brought up vulgar energy today have you noticed that? I love it it's good

you know we're getting towards dinner time it's getting dirty so how does the political thing you started volunteering for Cary right? yeah so I was doing this 10 power legal thing How does the political thing, you started volunteering for Cary, right? Yeah.

So I was doing this temp paralegaling. I was doing these open mics. Any real set goal in mind or just kind of kicking around seeing what happens? Just seeing what happens. I really, I didn't have a goal. I didn't know what I wanted to do. I was also playing a law school. I was just, I was my head, I was all over the place.

I didn't really know what I wanted to do. And are you finding a good tribe of people to hang with or is it still a little isolated? It's isolated. I lived, I lived with some, with one of my best friends and, but he got a finance job. And so he's gone. Right. He's one of those, when you get those finance jobs out of college, you're working 17, 18, insane hours. So I'm really kind of by myself in New York. And I don't really have much time because I'm working all day, then I'm doing law school applications, and then I'm going to whatever open mic I can

find on a website. But I ended up volunteering for the Kerry campaign, and that led to a very junior job in Washington working for a senator. And, of course, I took it. I had no nothing keeping me. I was just sort of, I was like, sure, that's a job. I'll do And of course I took it. I had no, nothing keeping me.

I was just sort of, I was like, sure, that's a job. I'll do it. Let me try it. Do they just take notice of you around the Kerry campaign headquarters? I wrote, so by the time I got to DC, a bunch of people had been kind of shipped off to various regional offices.

So the headquarters getting a bit quiet and they needed some help drafting very simple, unartful, inartful statements. Like there's a storm or there's an event where you just need a paragraph that says something like Senator Kerry wishes this team from Albuquerque a congratulations on their successful triumph at whatever, or our thoughts are with the people of New Orleans after hurricane Ivan or something like that. And I had ended up doing a few of those. And so when you were hilarious,

and they were the hurricane stuff. Oh boy. Oh boy. Category hilarious. Terrible. So, uh, the person I had interned for volunteered for intern volunteer same yeah uh it's funny at that time internships were unpaid obviously volunteers were unpaid if you were like a senior citizen you were a volunteer but if you were like under 25 they let you call yourself an intern right right so it felt more professional yeah but i was a volunteer yeah yeah that's what i was doing right but so the person I had volunteered for got a job after the campaign ended and remembered me and said, hey, we're going to hire one person. You want to come be this very junior press assistant in this Senate office? And I jumped at it.

I didn't know anything about the senator. I didn't know anything about working in the Senate. I really just knew nothing. And who was the senator? It was John Corzine, who was a former Goldman Sachs executive, then is currently best known for running, I think, a private equity fund or a hedge fund that misplaced a billion dollars. And they're like, where did it go, man? He's like, honestly, I don't know. It's truly crazy. I am embarrassed.

I remember the name, but I don't remember. Was he New York, New Jersey? New Jersey. New Jersey. Yeah. Okay. So I ended up working for him and I wrote jokes for some of his speeches. Yeah. And that led to somebody hearing word that there was somebody who could write jokes. So that's how I ended up writing some jokes for Hillary Clinton. And then when they were hiring a junior speechwriter, they remembered. And I threw my hat in for that. And that's how I became a junior speechwriter for Hillary Clinton. And that was where I was. For her Senate campaign. For her Senate office. Senate office.

Senate office. Okay, wow. Yeah. So I went from volunteering on the Kerry campaign to this junior press job, to this junior speechwriter job. Wow. And are you kind of surprised that your life has taken this turn when you were applying to law school? I was so in over my head, so completely. If I had been any more over my head, dead, dead person, wouldn't have made it. If I had been any less over my head, I would have been able to see how crazy what was happening was and have been unable to function. I was the perfect amount of in over my head because all I could do is get up super early, go there, pretend I knew how to write speeches and hope nobody noticed.

Totally understand that. Over and over and over again. I'm like 22, 23. I think that like, I didn't know this at the time, but the fact that they hired me was sort of almost like an admission of failure that they weren't going to find anybody with any kind of qualifications or that they thought could do a good job. Really? They'd gone through, if they tried a few people, it hadn't been working. They're like, well, let's just try some junior person and we'll have somebody more senior over. Let's try something. So I'm like going to the Senate building. I'm buying a giant iced coffee and a giant chocolate chip cookie every morning, just sort of straight to the dome. And then just like, I don't know, but I hope this

works. I hope she says this stuff and nobody gets in trouble. Here we go. Here we go. Sorry, New York State. Yeah. Good evening, Utica. Do they give you guidance? Yes. Yeah.

I mean, there's bullet points you got to hit and then you just do connective tissue, right? Yeah. It's basically rights itself. But so, no, like, there are really very serious policy people around. There's communications people. They're all providing input. You're not deciding about, like, her vote on

trade and stuff. No. Last to know. No, so I'm just turning... But the thing about it, when you're for a Senate office, so she's a very prominent person, obviously, but she's also a working senator. And so a a very prominent person, obviously, but she's also a working Senator. And so a lot of it is the Boy Scouts are coming to town or you're speaking to the Asian and Pacific Islanders Convention,

or the Suffolk County Realtors are having their convention and they're just sort of writing these kind of workman-like speeches that are just kind of meant to hit some key bullets, some policies. And that was sort of how I learned. I learned doing those less important speeches. But it really did take me,

it took me years. I really like, and it wasn't until there was another speechwriter who came on board when she was running for president named Sarah Hurwitz, who was a much more seasoned speechwriter. And it was finally, and there were other speechwriters who were around who were great, but it wasn't until I had a truly experienced speechwriter working with me day by day that I was like, oh, this is how you do it. What have I been doing? How am I not fired?

It's crazy. I told the Suffolk County Realtors to fuck off. And by the way, and by the way, I don't, this is not the version of the story I would have told for many years.

Yeah. It took me years to look back on this and be like, what the fuck were you doing there? And I was like, mad at myself.

Like, what? Of course you were fucking this up. Oh yeah. This is crazy. This is crazy. You're a 23 year old with a liberal arts degree.

What are you doing here? 1993, the reason I say I understand this, early days of the Conan show, it's the same thing. If I had been more over my head, I would have died. But I had to be somewhat unaware of what dangerous waters we were navigating. Of course. And looking back on those old shows, like which I can't do, we were terrible. We were awful.

And people are like, I love the old days. Like, well, you go right ahead and love them because I think they're awful. But I do think there is a point where, of course, you don't know how bad you are. You're bad. Yeah. You got to get better to learn what good is. Right. Exactly. I do think also part of it's true in any kind of creative field, but it's certainly true in comedy writing. It's true in speech writing. One thing you have to learn is how hard it is. Yeah. And I do think that when you're first starting out, you have the kind of the innocence of believing that it's like not as hard as you, it's just, you have your ideas and you write

them down and they're good and you're done. You know, it's like that. I also like, even if you've ever been in a, for anyone who's ever been in a writer's room, the first thing you learn in being a writer's room is is like, oh, wow, this is a fucking grind. Like you sit here for days trying to figure out what this story is going to be. Like breaking a story when you first, what does that mean exactly?

Why is it called that? It's called that because you sit there, you shut up, and we're going to break this story. It's going to take days. We're going to have to break it. Like it's a slow moving horse. Right. A horse that moves at a glacial pace. Yes. You have to break it. Oh, it's a slow moving horse. Right. A horse that moves at a glacial pace.

Yes. You have to break it. You have to break it. Oh, it's bucking. It's not moving. It looks as if it's not moving. And it smells fear on you. It will buck you.

Yes. Yeah. Because it's got the fear on you. Well, now, I mean, then you go on to work in the White House. And that's a different thing altogether. And you're writing, you know, this isn't the realtors. This isn't the Boy Scouts. So I spent three years learning how to be a speechwriter under Senator Hillary Clinton.

And then after her presidential campaign, if she loses to then Senator Barack Obama, I go back to the Senate office and sort of not really sure what's going to happen, what I'm going to do next. And then the Obama team, which Jon Favreau was leading, I'm not sure if I heard from him directly yet, but basically the Obama White House

was going to hire one more speechwriter. And I sort of threw my hat in the ring. And the way they hired is they had a blind speech test. They had a bunch of us write speeches, write the same speech, almost like a college final exam. Here's the topic, here are the facts, here's the issue, here's what we want to convey, write a speech. And so a bunch of people wrote that speech and mine was one that got plucked out in part because I think I'd had a unique kind of training. Yeah. Because I was on, I was in a Senate office, and then I was on the longest Democratic primary

that had been in many, many years. And so that was incredible training for being a presidential speechwriter. Very functional training. Yes. Yeah. Absolutely. And so then I went to work at the White House as a speechwriter. So then I went to work at the White House as a speechwriter.

And that was, I think, probably the first job I'd ever had where it was hard and it was nerve-wracking and I was anxious. And obviously the stakes felt so much higher. And all of a sudden you're realizing, oh, this is for the president. And then you kind of give yourself the yips a little bit because you kind of try to overwrite because now you think you're doing the Federalist Papers every time you open up the computer and you got to get over that. But ultimately I felt like, you know what, I'm here. I learned a lot about speech writing to put myself in a position to do this and was able to work on everything from economic policy speeches and science speeches and finance speeches to sort of the comedy stuff that the president gets to do. Yeah, yeah. And what was, I mean, is there one, is there a favorite that really stands out?

No. For me, it's more, I think you have like moments that you remember. I think it's like similar to any kind of writing where I'm sure you don't have a favorite episode, but you have a ton of favorite moments. Yeah. Specific moments or things like elements that you thought. Nothing is ever perfect. There's always things you'd want to do better. Yeah.

But there was a speech on the serious front. There was a speech he, President Obama, gave about health care right up in the run up to the passage of Obamacare. He was in Ohio, I want to say Strongville, Ohio. And he was talking about why he had come to Ohio. And he'd come there in part because a woman named Natoma Canfield had, I believe, written a letter about a medical hardship she'd experienced that Obamacare would ultimately have made more affordable. And she wasn't able to go because of her health condition, I believe. I may get the facts a little bit wrong,

but he gave this speech and he said, I'm here because we need to do this. And I'm here because we need to do that. And I'm here because we can ensure this many people. And I'm here because this many people haven't been able to afford to have silence. And I'm here because of Natoma. I felt really proud of that.

I remember that, like that feeling of like in the room, like, oh, that was, I'd like provided of that. I remember that feeling of in the room. I'd provided my comparative advantage. I did the thing that I could do and did it well. a great speech and there were speeches about i loved writing about space and science and he president obama spoke at the national academy of sciences and it was about every policy issue under the sun it was about energy it was about space and nasa it was about uh investments in research and development but a whole range of things and i really i really liked kind of putting that like framing that in a big way and trying to write something beautiful about like the power of science and yeah and then there were a bunch of different i don't really now at this point remember whose jokes were whose they're just who is gone it's gone by the moment it was done but i loved working on the correspondence in her speeches and i feel

really proud of those because i feel like even now people like you know, you know what? When Obama went to the Correspondence Center year after year, he really brought it. And I feel like that- And he can sell a joke. He's really- The best, the best. Yeah, he can really sell a joke. Is he funny?

Yes. Yeah, yeah. He has that dry, that wry sense of humor. And he would do, like we would always have a mix of jokes. There would be the kind of, I think we always found that the best mix of jokes, a bunch of us would do, like, we would always have a mix of jokes. There would be the kind of, I think we always found that the best mix of jokes, a bunch of us would write. We were a bit unusual in that, like, there were people inside the White House that were

writing a bunch of the jokes, plus getting a ton of jokes from outside. I think traditionally, a speechwriter would just gather a ton of material and shape it. But we were more like, we did a little more like player managers. You know, we would write a bunch of material. And David Axelrod, President Obama's longtime advisor, is a brilliant person. He's just very funny. And he would write these great avuncular kind of political jokes. And my platonic ideal of a political joke is pushing the podium in over,

and you all go fuck yourselves. Like that to me, that's funny. And so we would always i always feel like the and then john faber who's the head speechwriter was really great at figuring out the tone and the balance and like punching up the jokes and figuring out exactly how to get in obama's voice but i always felt like the best balance at those dinners and by the way tons of people submitted incredible material that made it possible but that like a balance between the acts of vuncular style and the like my kind of like you want a bunch of fucking piece of shit in here right right which is the energy i would always bring to it uh and if you get the balance right that's how you know you just kind of hit

the right tone yeah yeah yeah because again it's to be funny, but it also has to be functional. And it has to like, it's such a challenge because it, you know, you don't want to make more trouble for yourself. You know what I mean? You don't want him to say jokes that then, you know, just inspire stupidity. Well, it's going to anyway, you know. stupidity. It's going to anyway. I think a lot of politicians claim they want humor in their

speeches because they know that it's a value. But then in any one speech, is it worth making a truly funny joke? Is it worth the risk? And is that really what you want? Right. There's sort of two risks with a joke

for a politician. One is that it will be controversial or be seen as offensive or negative or not the right tone. The other is it just bombs and just does poorly. And we know that a bad joke, like a true terrible joke, a comedian bombing, whatever, like we know it just feels bad. It's worse than just boring, right? A bad drama is boring, but when a joke bombs, it hurts in your chest. And that's especially bad for a politician because the whole point of a politician being there

is to try to connect in some way, to relate, to prove that they understand what you're going through, that you're kind of on the same page. And then you tell a joke that bombs and it's like, whoa, we are not the same. We are from, we have, we do not share a sense of the absurd. We do not share a sense of, of what's funny.

You are nothing to me. Yeah. Get out of here. Yeah. So it is a little bit, so that's why it is high risk. So I remember, you know, those joke speeches, you just, that's the purpose of them. But a lot of times I remember President Obama would be like, I want more jokes at the top of some of my other speeches because they really do stick with people. Yeah.

But it's hard to find what that tone is. It's hard to like. When your political jokes are, fuck you. Well, right. Yeah. No, there was one that we did. There was, he was doing a speech on immigration and the border. Things, right. Yeah, no, there was one that we did. There was, um, uh, he was doing a speech on immigration and the border. Things never changed, but, uh, I'm laughing already,

but it was at the time where we were negotiating over a bipartisan immigration deal. And the Republicans kept moving the goalposts because we would say we will do bipartisan immigration reform. We will do the border enforcement you want. You want border enforcement, you'll get border enforcement. We will do whatever you want. And every time you concede and say, we'll do more border agents, we'll do more money for border security, we'll do more inspections, whatever you want. Every time they say they want more, they want more. And so President Obama went to Texas and he gave this speech about the importance of actually passing something. And he said, I've already given Republicans everything they want on the border. It's never enough.

Next thing you know, they're going to want to moat and they're going to want to put alligators in the moat. And it went everywhere. It went everywhere. And it was exactly what a joke can do in politics when it's doing what it's supposed to do, which is it was an on message point, right? Like Republicans are moving the goalposts on the border and they're being unreasonable. It was funny and light, you know? It wasn't glib about the seriousness of the issue in any way that was, I think, offensive to anybody. It was glib about their unseriousness.

It was making fun, it had the right target. And because a joke that works, people like it. It was on a lot of news broadcasts. It was kind of made, it made the rounds in a way that a serious version of it. It was on a lot of news broadcasts. It was, it kind of made, it made the rounds in a way that a serious version of that speech never would have. Right. And then didn't Trump actually do say something about that? Like put alligators in a moat? You know, here's the thing. Sure. Yes. I bet. Yes. I think he did. Yeah. Trump is like, you know, there's that, um, there's that book where there's that, that, that, that, um, it has every combination of letters.

So you can look up anything and it's in the book. Yeah. That's Trump's, that's Trump's repertoire. Yes. Yes. Yeah. He probably said there should be alligators. Yeah.

Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah.

Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah.

Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Well, now you come to Hollywood, you start writing for TV. What was the first one?

Was it 1600 it was so yeah so i again now it's like i was finally as i said i was like oh i'm you know what like i can do this i feel good about myself i think i was fucking things up left and right we always are but i was i had like learned the ropes right and now i'm feeling kind of not comfortable exactly but comfortable to take what you've learned and turn it into a tv show well more that i think that i felt i felt like i had i felt like i was i did i felt like i belonged to the club and so i had to leave because i shouldn't belong to a club that would have me as a member i see and so i'm getting all of a sudden i also feel like you get stuck yes yeah and Yeah, yeah. And I do think that that, now looking back,

and it was like, no, of course you should have stayed longer. It was a once-in-a-lifetime opportunity. But you were so kind of not insecure a little bit, anxious a little bit that, oh, like, I need to do something else. I need to do something else. And I'd always had this pull of wanting to do something in comedy.

And the longer I was, you you know when i was first in politics like you know you're what do you when you i was thinking about the west wing and like you know could if you imagine yourself doing politics and now when i was thinking about like what what do i imagine myself doing it was it was the west wing it was yeah yeah but it was now but it was like but then it became like oh now i'm here yeah now i'm doing it and now i'm like i want to do stand-up like that like the the little fantasy change right and so i decided you know what like i again like not pristine decision making i was i think i just turned 29 and had this realization that if i don't leave soon, I'll never have done, I've never been a young standup.

I was about to turn 30 and I felt like, well, I want to do this in my 20s. I want to do this at the beginning. I want to start doing this. And so I just- It was your comedy biological clock. Right, which is nonsense and not any way a person should think about it.

And not anything anyone really ever, no one else in the world has ever put, if you're not on a standup stage by 30, fuck you. Just pure mental nonsense that I did not test on another human being. Just, you know, sometimes you're thinking something, you can think it for years. If you said it out loud to one person,

it would fall apart. It's a hothouse flower, this idea. You can't be exposed to elements. Right, right. But so I had this dumb reason. But anyway, it drove me. And I said, you know what? I want to go.

I want to move to LA. I want to do stand-up. How am I going to do that? I don't have, I've been doing these low-level government jobs. I don't, I can't move to LA. to LA. So I ended up, because I had gotten some notoriety, I guess, for doing the jokes for President Obama, there are people that are like, well, he should write a comedy. Let's do a script. And so I started working on a pilot and I didn't know what it was. Did you get an agent first? I got an agent that I had met when they had come to the correspondence dinner.

Of course. It really worked this thing. Right, right. And they got me into a blind script deal, a term I learned about. By the way, that's the second ablest use of the word blind today. Blind speech test, blind script deal. Yeah. Something to think about.

Yep. Something to think about. Got to hold myself accountable. Totally trashing your deaf grandparents too. Yeah. But he won't hear it. Because he died 40 years ago. Right.

I know. But he could be a ghost in this room reading your lips right now. I wonder if deaf ghosts can hear. What a question. Wow. Never thought about it. Wow. Well, because they crown me.

It's like, hey, this being dead's not bad. At least I can hear. That's what you people sounded like. This sucks. What are we talking about? I don't know. Oh, so anyway,

I write, I moved to LA. I think I'm going to do standup. I think I'm going to learn how to write a pilot. But then Josh Gad has this idea about a ne'er-do-well first son. And he's like looking for somebody to help him write it. We meet, we work on it together with Jason Weiner, a TV director. And I moved to LA and within days, weeks,

I'm working on something that is going to be on television. And which again, I'm back to where I was at 22, 23, completely and totally in over my head. And look, I know what an asshole I am. I know it. I know. I know.

I know. I know. Like, fuck me. I know. I know. Take that away from this podcast that's yeah dancing between the raindrops i'm very lucky yeah i know i know but i'm just telling you what happened i understand i know you understand you didn't you know i know you understand i mean i'm sure that they were you stepped on plenty of throats on your way up the ladder.

But you just dealt the, you know, you played the hand that you shuffled the deck and got. That's exactly right. That's exactly right. But so I'm like, we work on this pilot together. I panic several times, stop replying to email for days at a time because I don't know what I am doing. I don't know what I am doing. I don't know what I am doing.

I downloaded the script writing software to write this thing that is going to be on the national broadcasting company. And it's like, what is anyone going to intervene and stop this? This is insane, but it happens. And wouldn't you know, it only lasted one season

but i learned an incredible it was very i we wrote 1600 pen cult classic that's what i say yeah oh absolutely and uh we all look we all know our characters from 1600 pen right who's your favorite character 600 pen the president oh you like the president oh the president people love the president any others the vice president yeah oh yeah good for sure for sure um you know uh uh i never saw this i never missed it you missed it what's it like to do you find that is there is writing for fake white house better than writing for real White House? So the thing about writing a speech is a speech is a story. But it's an argument, really. And you can use anecdotes and you can use examples and you can use data and you can use facts and you can use the speaker's experience.

You can use history, whatever you want. But you're ultimately just making an argument and it's A, B, C, D, E, F, G. What I found really challenging, and I didn't even understand how much of a skill it was, is when you're writing a television show, you're so far from writing it down. You start so far away from dialogue,

from just, you start with, it's a much more collaborative and I do think like technically challenging thing to do. And maybe part of it is because I had a lot more experience by the time I left speech writing. I had no idea. I don't think anybody,

I was a full fucking novice. I had no idea what went into making a tv show and so like it was so hard and i learned so much mike royce who was a long time uh raymond uh writer he came on uh and and he basically you know it was like he was the dad and i was the fun uncle. Yeah. You know, and he like he kind of really made sure we kind of kept this thing on the rails. And without him, it would have fallen apart. They usually hire like for the newer people. Yeah. They usually hire like a grown up to show you the ropes. Absolutely.

And that is what he was. And he was excellent. And I learned a ton from him. But I loved and I think what I am still far better at is like a funny joke, a funny line. I don't think I have the aptitude for like the structure. Yeah. I never, that was really hard for me.

It's still hard for me. Yeah. Like I just want to write really funny jokes and I want to write really funny conversations. Right. That's the part I want to do. That, yeah. That's of course what everybody wants to do. The hard part is, you know, yeah, yeah.

That's the hard part. Right. Um, you know, once again, I want to say, you got a book coming. Mm-hmm. Do you plan, like, do you see yourself writing lots and lots of books coming out? If I ever write another book, you play this for me. If anyone comes over to you, if anyone tells you that I'm thinking about working on another fucking book, you tell them that you play this.

And I said, no. No books. No books. No books is a stupid medium. It's stupid. It's dead. We've been working on this thing for a year. A year of writing this book.

I'm really happy with it. Yeah, yeah, yeah. We actually got the galleys of the book today it's called democracy or else and what i'm proud of is so it's called how to save democracy in 10 easy steps as it's it's um it's a sarcastic it's sarcastic right you know it's we know it's harder comedy yeah we know it's harder than that they're not easy steps right and it's actually a lot more steps we really think think about it. Right. But that's part of the fun of the book.

Right. But what I'm really proud of is, so it's me and Jon Favreau and Tommy Vitor who are my Pod Save America co-hosts and Josh Holloway

wrote it with us and he writes the monologue with Jimmy Kimmel. Really funny guy. But what I'm really proud of is I think that there's a lot of really funny

political comedy, obviously. And I think there's a lot of people thinking about earnestly how to keep people invested in democracy at a time when there are so many forces trying to make people cynical, make people turn away, make people not pay attention. And what I feel really proud of is we kind of put those things together. Because this is an earnest book, but we were able to do it in a way that i like i saw today i was like wow i cannot believe we made this joke in this thing

yeah we're gonna get in trouble i can't wait wow and i don't know what it's gonna be yeah yeah i don't know what's gonna get us in trouble right but like i think that especially in the Trump era, is not being cynical and funny is hard, but being earnest and optimistic and hopeful and funny is even harder. And that's what we're trying for. I've never, you know, on the Conan show, we were sort of, if we were political, we were silly political. And just because, and it wasn't, you know, because The Daily Show came out and this, it was like a whole new thing, you know, to be that pointedly political,

but also funny and engaging and entertaining. And I mean, I can only speak for myself, but I feel like the whole show sort of felt like, we don't know how to do that. Like, and we're not interested in that really. And I find, you know, like I'll write wisecracks on social media and stuff, but to really make political humor, like I don't know how to make that funny. Well, I get, you know, I get worked up and bummed out. And, you know, I've, I've heard you say a version of that i've heard

conan say a version of that and i think it is true in the sense that obviously not doing like partisan policy and political coverage right but i do think being silly and joyful and open and embracing of weirdness in the way that show did is an act of politics. It is. It's a, it is a, like, everything is political. Yeah. And that is a, I do think that that is a kind of politics. I see what you're saying. Yeah.

You know, I would say, you know, you look at Leno and then you look at Conan. Both shows that would say, oh, we don't do politics. Yeah. But I would say Conan has a political point of view that I admire, that your show had a political point of view I admire in a way that I think other shows that would say they are not political, I don't. Yeah. And that, and then you can do that while never talking about the latest state of the union. There's a reason I think that so many people still talk about how much they love that show, even though it wasn't political, because it was it does have a politics. It did have an impact on people who all together have a worldview, you know? Yes. Well, and there certainly, there was real, you know, the people had politics. Of course. You know, but that it just didn't really come out on the show because, you know, we just,

there was like, and I think it also too is because we predated, you know, we got on the air before anyone was kind of doing that. And it would have felt like you know like copycat if we had if we had tried to sort of emulate something else and and i i i you know but i i see what you're saying and it's nice to hear and i guess you know like we were sort of as subversive as two white men in suits you know doing doing bits with puppets and, you know. Yeah, but that's, yeah, but no, it's, I don't know. I'm thinking about it.

It's like, what does it mean? Like, you know, okay, it's apolitical, but it is just by saying this is possible on television. Yeah. Is defying a convention and saying, hey, these rules don't apply. And a bunch of young people watching a show where a bunch of other people are saying, look at these rules. You didn't even need to follow any of them. That isn't conservative. You may not be political, but it's not conservative. I was just thinking, yeah, absurdity is more liberal. It's more liberal. If you're into absurdity, I don't think you're thinking, you know, we should close the borders.

Right. I don't think the Venn diagram with people who like masturbating bear and people who think, right, right. And people who like Trump, I don't think that Venn diagram has a big overlap. Yeah, yeah. Well, that says something, doesn't it? I think, yeah, maybe more political than you'd want to admit. Right, exactly. I think we did way more than The Daily Show ever did in terms of contributing to this country. Yeah, and I'm always saying that.

Sure, anybody can say what they think, but to feel it, you know? Right. Go ahead and preach to the choir. We're writing their music. Jesus. God damn it. Pretty good, right? That was good. I wish you were's pretty good right that was good i wish that was good speeches that was good look at that still got it huh still got it all right well okay smartest

smartest smartest closeted gay guy in the business i've always said that about andy oh sharp as a tack sharp as a tack and horny for uh to be a closeted gay man would give me such an air of mystery that i do not possess now yeah i'm just plain old straight wink wink okay you got you're doing live shows across the country love it or that's right okay first of all the book democracy or else how to save to Save America in 10 Easy Steps. It's being released on June 25th. I got to say one more thing about it. We are donating the proceeds, the profits from the book.

We're donating them to Vote Save America. You fools. I know. I know. It's so dumb. But we're going to use the money to organize in 2024 and beyond. So this is a book about what people can do. And we want you to know that the money is going to go to organizers and people

on the ground doing really good work. So please, it's a, it is a, it is a, we, I'm very proud of the book and the proceeds will go to actual good work. And we have a whole team that vets organizations to find the places where dollars will go the furthest in key races in key in key places so consider it okay that's great thank you for doing that thank you yeah um love it or leave it tour hell yeah uh with the simple mission of making you laugh until you forget how old joe biden is that's a lot of laughing. And you're also, you guys are doing live shows across the country with Pod Save America. That's right. Pimping that book.

That's right. Yeah, yeah. You got to get out there and sell that shit. You got to always be hustling. Always be hustling. Before we end, you know, this three questions gimmick that we have. What's the main thing you've learned from coming this far in your life? I would say that there is no room,

there is no place where everybody's got it figured out and they're just not telling you. There's nobody with all the answers. Everybody is making it up as they go. If you see something that doesn't make sense to you, incompetence is almost always the better explanation than malevolence. That if you feel like you don't

know what you're doing, have no fear. Everybody else feels the exact same way. And that can be disempowering and it can leave you feeling like nothing matters or. Or scared. Or scared. Or scared that there's no one at the wheel. Or scared that there's no one at the wheel. Or it can lead a lot of people to think, oh, then conspiracy theories. There has to be some explanation.

There has to be somebody pulling the strings. Or it can lead you to feel like, you know what? If nobody, if there's nobody out there who's got a better handle on this than I do, then I can figure it out. Yeah. That's what I got. That's good. And I do think that's what I always feel about conspiracies.

I feel like, have you worked with people? Have you worked with human beings? Have you tried to get things done and then also keep them secret? Yeah. It's impossible. It's bananas. And it is. You think we faked the moon landing?

You think we faked... You think... You think this government... Right. Faked the moon landing? Do you see what happened when we tried to make a mask? Really? What are you talking about?

Oh, John Lovett, thank you so much for coming in. Thank you for having me. It's really been a lot of fun. And I thank all of you for tuning in to this episode of The Three Questions. And I'll be back next week. The Three Questions with Andy Richter is a Team Coco production. It is produced by Sean Dougherty and engineered by Rich Garcia. Additional engineering support by Eduardo

Perez and Joanna Samuel. Executive produced by Nick Liao, Adam Sachs, and Jeff Ross. Talent booking by Paula Davis, Gina Batista, with assistance from Maddy Ogden. Research by Alyssa Graal. Don't forget to rate and review and subscribe to The Three Questions with Andy Richter wherever you get your podcasts. And do you have a favorite question you always like to ask people? Let us know in the review section. Can't you tell my love's a-growing? Can't you feel it ain't a-showing? Oh, you must be a-knowing.

I've got a big, big love. This has been a Team Coco production.