Conan O’Brien Needs A Friend - Rachel Sennott

Episode Date: November 10, 2025

Actress and comedian Rachel Sennott feels included about being Conan O’Brien’s friend. Rachel sits down with Conan to discuss her new series I Love LA, depictions of influencer culture, experiencing a Saturn Return, and being arrested in the Cayman Islands. Plus, Sona takes up a new babysitting job. For Conan videos, tour dates and more visit TeamCoco.com.Got a question for Conan? Call our voicemail: [phone]. Get access to all the podcasts you love, music channels and radio shows with the SiriusXM App! Get 3 months free using this show link: https://siriusxm.com/conan. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hi, my name is Rachel Sennett. And I feel included about being Conan O'Brien's friend. Fall is here, hear the yell, back to school, ring the bell, brand new shoes, walking blues, climb the fence, books and pens, I can tell that we are going to be friends. I can tell never we are going to be friends. Hey there, welcome to Conan O'Brien needs a friend. I am joined, as always, and I'm very fortunate to be joined by Sonoma Sessian and Matt Gourley. Hi.

What's going on, gang? Well, our very own Eduardo is actually going to do a career day at a high school to discuss what he does here on this show. Oh, my God. Wait, so how did this unfold? I have a cousin who teaches at Altiloma High School in Rancho Cucamanga. He kind of knew what I did and was like, wait, who do you work for? And he said, maybe you should come speak to my students. Cool.

I think so. And I was really like up for it. And I was like, yeah, I'm totally down for it. Let's do it. And then I was telling these guys that it hit me yesterday that I'm terrified about speaking to high schoolers tomorrow. Yeah, same. I don't know how to market what I do. So maybe you guys can give me some.

pointers on like how would you sona you have practice with this no one is tighter with the high school community than i am especially in rancho kookamonga you are speaking my language yeah well you know one of the things i would say is if you were talking to people that know the podcast and a lot of people do it would be very easy but you're going to be talking to kids who may not know what this is but they know what podcasts are right i called my cousin as i had that panic attack and i was like all right prep me what's what's my audience and he's like look there's a chance a lot of them don't even know who conan o'brien is yeah and i said great because i was going i was going to start with that so that gets me nowhere um but then i thought to gets me nowhere according to my cousin not to me

sure sure sure i'm just saying that was my instinct no no and don't i don't take offense to the phrase conan o'brien gets me nowhere which we which maybe we should replace needs a friend i say that Every morning when I wake up. But then I thought, you're brushing your teeth. Then I thought, okay, who are some guests that we've had on that maybe would resonate? So I was like, the first person that came to mind was Billy Elish and Phineas. I'm like, oh, that's a guess I could probably pull and point two. Yeah.

Are there any other guests? Rama manual. Yes. Yes. You know, whenever I don't know what to say to kids, I just bring up I know Rama manual and it kills. Perfect. What grade? What age?

I mean, it's freshman through juniors. Oh, so it's all of high school. Oh, my. You know, like Ryan Reynolds or Han Solo, you know. Okay. Yeah. I mean, I don't know that Hans Solo. Deadpool.

Dan Reynolds would help us. I thought about Al Pacino, but then I was like, no. No, they don't. No, they don't. They don't. That's like saying I knew Woodrow Wilson. Woodrow Wilson came in. Have we had the K-pop Demon Hunter girls on yet?

No. You would score. We should. See, this is why. Hunt tricks. Yes. Yeah, I'm in. Hey, I'm in.

Are you? Six, seven. What is? Oh, my God. That was so uncomfortable for me. I did think about saying six seven like a bunch of times. Just say six seven. I've had, I had some young people in the Philippines shout six seven at me and I, you know, I don't know what happened.

Is 69 done? What? You're making it. In my life, yeah. It's been done for a while. do that and like you wouldn't remember when people were like turn to page 69 and everybody would giggle yeah we don't do is that no it's six seven now okay what is six seven uh no one seems to exactly no no one seems no adam has kids who are a little older than ours my kids say it all

the time uh they they couldn't really tell you when i when i ask them what it means they do that and they and they say the six seven but is it 69 related no no not at all six same it comes from originally from a rap song correct oh Talking about La Mello Ball, NBA player. This is your opener. What does that have to do with podcasts? Do we do any cool things? Can I say something?

I would say never mention the podcast or what you do. Even though you've been invited there to talk about what you do, it's career day. Just show up and go like, hey, 6-7, everybody 6-7, yo, yo, yo, 6-7. And then talk about how you like Billy Eilish. And then maybe talk, look up what's the latest thing that's trending that's gone viral. I was going to show a clip of you on Hot Ones, maybe. Yes. Oh, there you go.

This is who I worked for. Oh, no, no. People buried in graveyards know that I did hot ones. So, I mean, I'm talking about corpses. Corpses, long dead corpses of pilgrims. Okay. People that died in the 1600s know that I did hot ones. Sure.

Do you think if he shows them, if he shows that clip, though, will they be like, who is this guy? Or do you think they'll be like, oh, he seems cool. They will say that lady looks insane. That's what will happen. That lady looks like she's in great distress. I hope that lady recovered mentally. Can I say I do think that a lot of kids in high school know who you are. I think so.

I think we're making jokes, but also you hosted the Oscars. You've done a lot of stuff. And high schoolers love the Oscars. They're all over it. They'll remember my costume changes. They'll be all over it. I don't know. I think that a lot of people know who you are.

Well, I think to give you real advice is the more you can, can just keep it personal and grounded and just about this is what I do. You know, you listen to podcasts or when you hear of them because everyone, they're listening to some podcasts, you don't realize what the technology that goes into, what you actually hear. I mean, that's cool stuff. Yeah, I did think about setting up like a little faux podcast set up in the classroom and maybe having them sit and just play the role of hosts, play the role of guests. No, you're really good at setting up a faux podcast studio.

Nice. One, you're cool. You're just naturally very cool and likable, so you should be fine. I started with a long prayer. Okay. They can be very intimidating high school kids. It's three periods that I have to speak to back to back to back. They're 30 minutes each.

They're very scary. I'm sorry you hit me. I got terrified. You know what? Can you show clips at all? I can. Yeah. Yeah.

I mean, look through. I don't know who we've talked to that would resonate with high school students. But, yeah, Ryan Reynolds and Billy Iowa. So two, how many episodes? It came to mind. Oh, yeah, Michelle's honor. How about Iowa Debris? Oh, yeah.

There you go. You see, I knew. You know, this makes me think we should only be having people that high school students know on the show for a month. We should do a month of just. But then we won't know who they are. That's okay. They'll write some notes from me. And then I'll know, you know.

Six, seven. Stop doing it. I don't know what I'm doing. You guys are killing it. I never birthed it. I know, but like when you start saying it, that's when they're like, oh, no, now it's lame. But I'm not trying to say it to do it. Now I know ASAP Rocky.

Oh, yes. You should just say, I work for someone who knows ASAP. Who knows ASAP. Who's in a movie with ASAP Rocky. And then they'll be like, we don't know who she is. But ASAP Rocky, yeah. Yes, I love it. Okay, so get ASAP Rocky on the podcast now that you brought him up.

He says he wants to do it. And it's Ireland the creator. He says he wants to do it. But he said it in that way, like, I've got to get rid of Conan. Hey, I should do your podcast someday. Man, I got to go. And then he's suddenly unavailable all the time. Yeah.

Okay. And I keep calling him and Rihanna picks up. And she's like, he's not here. And I hear him in the background, good, honey, good. Good, honey, good. Good, honey. That's good. Just as I instructed.

Who says just. as I instructed. Well, apparently. Honey, good. Good, honey, good. That's how he talks. That's ASAP for you. Or as I called him when I first met him,

AKA Rocky. No, you didn't. No, I did. I'm kidding. Oh, my God. I would have been horrified. Oh, my God. Oh, my God.

And he went, ASAP. And he went, hmm, me suppose. You rapper, you, that's what I said. Okay, honey. Well, I'll report back. All right. Yes, I want to hear how this goes.

I do, too. I want to hear how it goes. Unless it went badly and, I don't want to hear a lot about how they knew nothing about me. That's going to be horrifying to me. Just make it up that they went crazy. We loved him in the early 90s, they say. My guest today is an actress, comedian, and writer who starred in the hilarious movie Bottoms.

Now you can see her in the new HBO series, which she also created and co-wrote, I Love L.A. I'm very excited she's here today. Rachel Senate, welcome. I feel included about being Conan O'Brien's friend. Okay, so that's a sentence that doesn't make sense phonetically or grammatically. But what I'm thinking of, do you remember when we both gave speeches? Yes. Well, you hosted.

I gave a speech. Yeah. What was the event? It was raising money for a children's hospital. And I remember I took a big cut of what they raised that night. You did. That's part of my deal. And the children's hospital didn't know that.

And they were, and I said, no, no, no, I get 80%. And they were like, but the children, I said, fuck that. Remember that? Yeah, yes, yes, yes. And the children were there crying. And they were upset and you said, too bad. Too bad, bitches. But other than that, it was lovely.

Other than that, it was so. It was really fabulous. They would have. They would have. They raised actually tons of money, even still, the 20% that they got a key. I want to start, I know we've already been talking, and I've been really looking forward to this because you came to my attention when I saw Bottoms. I was really charmed by it. I really liked it a lot. And then this morning I woke up early because I'm jet lagged from I was shooting in another country. And so I watched it again this morning. Bottoms? Bottoms? I watched it this

morning. Oh, my God. And I was just like, yep. I also wonder how it hits at like six in the morning. And I'm like, it feels very different at 6 in the morning. Guess what? It still works. It still works. It still works. It's really funny. Oh, my God.

And down to one detail I love is the football players play on a field that has a, like, a massive 200-year-old tree on it that would never exist on a real football field. But you guys had it there because you needed something to happen and you didn't give a fuck. And I loved it. And I'm sorry, I'm swearing so much. I'm not going to do that anymore. Are we not supposed to swear? No, no, I'm just doing it too much. I know, but I'm doing like I'm just a sailor that just got on Shirley.

It's cool and edgy. Yeah. It's making me want to swear. Well, I shouldn't do it. It's not right. It's not right. It's not right. I heard you were coming on the podcast and I thought, well, I don't know what Rachel's promoting.

And they said, well, she has this new show. It's going to be on HBO. We're sending you five episodes. And I thought, five, you know, I'll watch one. I'll dame to watch one because my time. is so precious. And last night, my wife and I click on. We watch one. Love it. And I go, there's another one. We watch two. And I say, another one. We watch three. Another one. Four. And then my wife is always going to bed at 9.30. And she's like, I think I have to go to sleep. We're watching another one. And suddenly I'm Mussolini, yelling in the house. Screaming at your wife. Screaming at your wife. Screaming at my wife, dogs, cats. And I watched five of I Love L.A. And it's really, really fun. That's my compliment up front. No, it's huge.

I feel like I do the same thing when people send me like a chunk of stuff. And I was saying this to you before. It's like, I'm like, I'll skim through. I'll write down like three moments than I like and then I'm done. And then I can reference them and be like, see, I like all these three moments. I watch the whole thing. So watch, unless you're lying to my face. But that's okay because I felt.

You'll never know. I'm a sociopath. Me too. I'm people pleasing. What is so hard? Why do we have to have her on? I hate it every second of it. I hate her on. Get her out of there. No, but I, that means a lot because I think, like, we wanted to create that driving. Like, my favorite shows that I watched in college are like those Sunday night shows where you leave and you're like, I can't wait for next Sunday and I want to know it. Like, I want that pole. And also, like, it's very much of the generation, whatever, but I hope that it's funny to ever. You know what I mean? And brings you into the world and doesn't feel like this is only for these people. Like it's for, hopefully for anyone who wants to watch a bunch of girls text each other and talk and hook up with people and talk.

Well, I might be a pervert. You're also describing my life. Yeah. You're like, that's my Wednesday, honey. Me and the girls. Matt is constantly texting me and sexting me. And then, yeah, and then we get together and we have a Haley Bieber shake. And, you know, so we know what's going on. Yeah.

I felt seen. Did you identify with one of the characters more? Did you feel like you're like, I'm totally a Tallulah? Well, I'm team Maya. Isn't that your character, Miami? I'm Maya. Yeah. I identified with the fact that I came from the East Coast.

Boston, then went to school in Boston, then left in, this will really date me, but 1985 with my writing partner, Greg Daniels, and we went to L.A. And I thought I had been dropped on the surface of Mars. And your show is very much about someone who comes from New York. Yeah. And you come to L.A. and you think your friend is coming with you, and then she doesn't. Yeah. And you have to make a go in L.A. And I have to tell you, I remember, that so clearly. And so, yes, the references changed. There wasn't social media. There wasn't the kind of business that your character's working in. There wasn't oat milk. There wasn't, you know,

chai. We didn't have that. But what I remember, it was. And you came here? There was no milk either. No milk either. And there was no Haley Bieber smoothie. Yeah, there was, there was, there was, there was war rationing. Yeah. Because World War II had just ended. Okay. So there was, uh, they put an embargo on all Haley-Beber smoothies back then because they knew should be born in like 60 years. For the war of war. They needed the college. We need a Haley-Bea-Smoothie for the war, says FDR. Back on Victory Garden to make your Haley-Beber shake. So that didn't exist. But what I remember is, you know, when you worry about the references, the references can change, but the fundamental elements don't change, which is it's horrifying to come out to L.A. when you grow up in that other coast.

And I was horrified. I hated this place. for a year and a half, absolutely hated it. Which is short for the amount of time to hate it, to feel like what the fuck is going on, you know? Like, I also just felt, like, weird. Like, everyone was like, you talk so fast and you're really stressed. Like, it's like, I're like, I need to get on your guys's level, but I can't, you know? It's crazy. You can't.

Matt and I are the locals that are like, it is fast. I feel scared about going to New York. Yeah, that's why I get scared, too. Same thing. The rhythm's different. Sona has been my assistant for a really long time. And Sona came with me, I think it was 2011 or 12. And you came to New York.

And Sona has grown up here. She freaked out about cabs. I remember you freaking out about cabs and saying, I don't want to sit in there. Other people have sat there too. You make me sound like such a princess. But I'm sorry, you were. It was weird.

It is weird. It is weird. But, you know, it is a completely different rhythm on the east. It's so much more intense. You're like, I have my car that I cry in and I eat luncheon out of a container. I vomit in my own car.

Yes. I puke in my car. Yes. Not a stranger's car with other people's pew. No, you have your like, your haven in your space, and then it's so jarring and weird. And then like you, I feel like also once you've lived on both, you're never over either.

Like it feels like I'm like, it's like I forever. have, like, two boyfriends or divorced parents or something where I'm like, yes, you're constantly is a push and pull. And people always say to me, they want me to declare, yeah, L.A. sucks. I like New York. Or, you know, I'm done with New York. It's L.A. man. And it's not, neither one is true. Now I like them both. I see the strength of both. I think there are cliches about L.A. that just aren't true. Yeah. I think because L.A. is a much larger. surface area, there's so many different neighborhoods that are constantly, I mean, everyone gets

gentrified eventually, but they keep inventing new neighborhoods where artists can live. And I think there is amazing art, artistic output in Los Angeles. It's just not shoved in your face. You can't just walk down into Greenwich Village, and there it is. Meanwhile, in New York, I don't know how an artist would survive in New York now, because it's, it's, everything's a gap and, you know. Everything's, oh, an actual gap. I was like, yeah, there's a gap of, and then I was like, no, a gap, a gap for Azara. It's a gap in Azara. A friend of mine and I were walking around and we tried to find CBGBs and it's like a varvato store.

Is it? And we were in like this store and we were looking at the old CBGBs and we were trying to remember like, how's this layout? Yeah. And a guy who worked there who was trying to show us like a jean jacket said, oh, no, no, the stage was over here. You know, ignore these beautiful pants. This was the stage, and that's where the Talking Heads performed. And that's where the Ramones were. The Ramones were by the Blazers.

Yeah. And you're like, fabulous. I can feel the history in here. Wow. The $90 T-shirts. That's where Blondie performed. You inhabit this other one. world that I have some familiarity with, which is writer slash performer. I mean, you've written

so much, pretty much all this stuff that you've been in. Haven't you written just about everything? I guess starting beginning of my career, so I.O. and I did a Comedy Central, like, web series together. That was like three episodes. Shiva baby, I didn't write my friend Emma Seligman, who directed it wrote. And then M. and I wrote Bottoms together. And then this I wrote. This was the most I ever thought as an actor, or, like, on set, I'm, like, barely thinking about acting because I'm directing, I directed the finale. Right. You were a lot of hats.

I were, it was, it was, yeah, it was, like, and then prepping, and then we're rewriting stuff, but then we're editing the show while we're shooting it. The good thing is my character is, like, stressed, so I was just like, I don't have to go. You know what I mean? You should make all of your characters stress. Yeah. I kind of have, in a way. Yeah.

It's like, I'm kind of easy. they're stressed or stupid, or both. It's like one of the, there's like two sides to me and it's somewhere in that space. A stressed, stupid young woman. If I ever have to, if I ever have to pitch you something, if I write a script and I want to pitch it to you,

I'm going to start everything with a stressed stupid woman. Moves from L.A. to New York or New York, L.A. A genius idiot. Yeah. But it was like, you know this it's like balancing those things and being like kind of which role do I need to be the most today like there was a day like there's some days on set where I was like I'm more of a writer today than an actor I'm directing today but then there were days like there was a day that I had like a multiple sex scenes which by the way oh my god this was so funny because

it was like all the sex stuff in the show I'm like I wrote or was in the room for writing and I think like for me like sex and stuff like sex if you're going to show it in a show or movie like it should be like funny it should tell you something about the relationship because I think if I look at my relationships I can immediately tell like where we are based off of like how the sex is do you know what I mean definitely okay do you feel that way too you're talking to the wrong guy okay literally a virgin I just mean okay sorry I'm sorry I'm I agree with you. Do you know what I mean?

No, well, explain what you mean. Well, it's very different in the beginning than it is. No, he means explain what is sex. Oh, sorry. What goes where. Okay, totally. Show me with dolls. Oh, God.

No, no, I'm kidding. I'm kidding. But anyway, yeah, I know what you mean. Yes, yes, yes. Like, where I was like, I want all of the sex to feel like it's in the show for a reason, basically. Well, in the pilot episode. Yeah. Opens with you and your boyfriend having sex.

and what's funny about it is an earthquake. I'm not giving anything away because it's really the beginning of the first episode. And I thought it was a really good opening. It's L.A., so there's an earthquake. And he's like, oh, my God, there's an earthquake, but you're close to orgasming and you just want to keep it going. So you tell him, I think it'll be all right. It'd be all right.

And then the earthquake stops. You keep going. And then the earthquake starts again. And he's like, no, I think we really have to, like, get out of the building right now. And you're like, eh, almost, eh, I'm almost there. Can you just choke me? And I was like, okay, there's a familiarity here that happens when you're in a committed relationship. Yes.

There's a familiarity, but there's also, and it's a little, it's a little like utilitarian. Yes, it's almost like, do the three things that I need. Really quick. Yeah, yeah, yeah. Like, I'm almost there. You did wanting to finish her off. Right. You know.

So it was not, to your point, it was not in any way gratuitous. It was funny, and it was telling me right away how your character's funny. These people are connected in a very familiar way. Yes. And so, yes, you're right. It was not just we open on sex scene so that we can get the viewers in. It was, it accomplished a purpose. It accomplished a purpose.

But it was really funny to me on this specific show because, like, we, of course, had an intimacy coordinator, but she would, like, I would have a conversation. with her as like the showrunner and be like you know like we want to hear what the actors are comfortable with ideally this scene accomplishes like this sort of feeling or like we like to shoot it this way whatever and then she would call up the actors but so i would have the conversation with her as the showrunner and she would be like totally and then she calls me like 30 minutes later and she's like so this is what they're thinking i'm like i just talk to you love she's like you tell me what you feel comfortable with in the scripts that's hilarious in the script you're giving a

blow job. Yeah. Do we even want to go there? I'm like, I wrote that. I'm like, what? And so she's like, I know, but are we going to do that? And I was like, yes. I yes. Like, so that was so funny and sort of bizarre, like going at that from like two angles, whatever. There was a day on set where I had like an emotional scene and then like, I'm not going to say what it's happening because it's sort of give something away. But sort of two sex scenes in a day. Sort of it was like sex scene, sex scene, lunch, beans for lunch. And then like emotional cry scene.

And that day I was like, today I'm an actor. Like today I was like, and that's when you have your team of other support. Like I'm like, MF, there's questions about alts. You got it, girl. I'm naked and I'm crying. You know what I mean? But then on another day you put on the other hat and you're like, today I can answer the questions about that.

So it was interesting, like, balancing those, but, like, finding what thing you were leaning more into on the day, if that makes sense. Well, what makes sense to me is a lot of my career, starting with the late-night show, I can use my thinking head when we're thinking during the day, when we're working on the show. And then when it's time to go, it's 5.30, guests are here, band is playing. I need to get makeup on, and I need to let all that go. and then be the guy who's just in it. Yeah.

And if the guest put something out there that's a surprise, drop everything you thought about. Yeah. And go that way. Go there. And go there because that's what's happening right now. And I found that, and I don't know if you can relate to this as an East Coast Catholic. What I can, you know, you're Italian, is that right? Half, half Sicilian, half Irish.

Okay. My God, you're screwed. Well, as a 100% Irish, but we both come from very similar. stuff. And what I can relate to is there's this combination of restraint and busting through the restraint. And that's where this magical thing happens. Yes. But we like control. We like control, but also we secretly love the loss of control. I know. Sorry. I almost was like, girl, yes. You can call me. Trust me. You can call me girl. I was just saying that, I mean, that's the whole Catholic thing. That's why that it's a yin-yang. It's where, yes. That's why it's like,

it's like you're like, why are you guys freaks? Not saying you're a freak, but I'm just saying Catholics. Do you know what I mean? Because you live in this push and pull of like control, not control, whatever. But I feel, yeah, I'm always reaching for control, whatever. But the most beautiful things happen sometimes when you just are like in flow, free flowing. And you're right. It's like those things are a gift.

And like when something goes wrong on set or whatever, it turns into the funniest moment or the most beautiful moment. But I feel that way, too, where I'm a planner. I like to know what's happening. Which is good. That's the lesson of all of this is it's not good versus bad. It's you need both. And then another part of this that I find fascinating, which I know nothing about,

and I'm freely admit I know nothing about it, but you play someone who you're best friends with somebody, she's an influencer, you were helping her be an influencer. The idea was you were both going to move out to L.A. And you're going to manage your friend who's an influencer. she decides to stay in New York, you go it alone. And so you're working at a company where you're managing or helping to take care of influencers. I know nothing about that, but I also know that it's a huge part of an industry right now, maybe the industry. I haven't seen it depicted yet.

I was watching the show and I was thinking, oh, my God, you're right. These influencers who make a funny video or a meme. And they're holding a bag, a certain bag. That is a business. Yeah. They're making a lot of money. Yeah. They're getting sent a lot of products.

And of course there would be a management system for them. And I don't know anything about it. Yeah. I mean, no one's people actively don't want me making videos where I hold a product. Yeah. I actually want that. I'm like afterwards, we'll do a video of you in this bag. Yeah.

I've been paid a lot of money not to hold products. Not to hold a purse. Yeah, exactly. No, but I felt like, I'm so happy you say that because we kept talking about the show, like a reference point being like entourage for internet at girls. Because we were like, I feel like we've seen Hollywood done a lot. And I feel like the internet is such its own world and business.

And it's not separate from Hollywood. There's crossover. But I think like I was like, this is how I came up. I came up being online. Any of my friends who are like working in this. now came up online. I also know people who just do that. That's their only job is like the internet and their videos or fashion or whatever. And so I think also like the internet people like sometimes struggle to show the internet in film and TV because it moves so quickly. Yeah.

It's evolving so rapidly that if you try and depict it and your project isn't coming out for nine months, you're behind. But the time it comes out, people are like, well, that's lame. Yeah. No one does that anymore. It's very dated. And so I was like, the way we tried to do it was make our own internet in the show where it moves and lives and breathes in the same way like the internet does. But we don't reference anything specific. It's like exists in the same way as it does for us where it like informs all the characters' lives. It's part of their lives and their business.

But we don't, it doesn't, hopefully, doesn't feel clunky or like, yeah, we, we, we. you get it. You know what I mean? Because no one wants to see. The other thing we kind of took from entourage is like, you don't see too much of like Vince acting. You see like his world and his like friend group and their dynamics. But it's like you, that's what he does, but you don't see it. Like it's like we don't need to see Tallulah posting every second. Like we get it. In the Dick Van Dyke show, which is the, you know, oldest reference I can come up But this is literally, it literally starts, that show literally starts before I was born. So it's old even for me.

Yeah. But when I was growing up, that was a show about, for you kids out there listening to this interview, that was a show about a comedy writer. And that had not been depicted yet because they think this is a time when, you know, people are, everything's so meta now. People all know behind the scenes. Yeah. Everyone's so savvy. Yeah. But back then, people honestly didn't think that I think shows were writing jokes.

Writing, you know, that's just Lucy. Lucy's cookey. No, no, she has writers and they work all of this out. And it's, but, so it was a show about a comedy writer. And what they never did was they never really showed you the sketches. Yeah. And I thought it was all of them. Well, I think we got it for today.

And then it was about their lives around that. And it's the same thing. Yeah. All these years later, I always, it's pulp fiction. Yeah. They never show you what's in the suitcase. It's just a light. and it's such a smart thing to do,

but that's Tarantino saying there's this thing that's incredibly valuable and everybody wants it. And you don't even need to know any more than that. No, yeah, that's the whole concept. That's what matters. Yeah, what you said about the Dick Van Dyke show, which I'm familiar with,

but haven't really given it a full dive in. It's in black and white. Should I check it out? I'll colorize it for you. Okay, perfect. You'll put it in a little 30-second clips and you'll cut it together with a video of someone playing with slime

next one. And then I can watch it. It'll be someone unwrapping. Unwrapping a box and then Dick Van Dyke's in there doing his schick. I love it. In 10 second clip, so I'll go, ooh. Yeah. But like the same thing.

The other thing is I was like, nothing is really new. Like I think I felt certain times during this where it was like, I've got to make something totally new. And like, you know you're going to be compared to things and you want to do your own thing. But it's like everything is like from what comes before it. but you have to take, you know, your own blend of references and ideas. At the end of the day, people are people, like, relationships or, like, this era, the moment of, like, your late 20s is always, oh, I want to know about if you had a Saturn return. Did I ask you about that? What?

A Saturn return? No, I don't know. Yeah. Are you going through yours right now? No, I'm 32. Okay. Wait. But did you, a Saturn return is like end of your 20s.

Oh, oh, my God. I thought you were going to return a car, the Saturn, because of a defect. That's where I went. So I thought, well, if you're not happy with the Saturn. Do you think Joe couldn't return her Saturn because she's 32? Joe couldn't measure on her Saturn. That's a policy that they have. That car company has been defunct for 15 years at least.

I don't even know what it is. I only know because Dick Van Dyke drove a Saturn. Dick Van drove black and white Saturn. No. I want to know about this. Yeah. Okay. So you're into astrology.

I am. Okay. Tell me what Saturn return means. Okay. I have so many questions. I'm going to maybe need to pull up your chart or, like, diamond. Because do you know what sign you are? I'm an Aries.

An Aries. Yeah. What does that mean to you if I say Aries? In Ares, you're a Virgo with the backbone. Okay. I don't understand. Okay, totally. But you're a Libra.

That's kind of a pussy. Do you know you're rising in your moon? No, I don't. Okay, we'll find it later. But basically, and Aries is like fire. right don't mess with you but you have like an order to you like you could have a you a temper isn't what I would say but it's like fiery and it's like don't mess with me don't mess with the people I love I would say I have I can be intense you can't I think because you're particular about how you

like your comedy to be yeah and I think if people hinder that or or overwork you in a certain way there's so many things that I don't care about and then if it comes to comedy yeah something where I'm supposed to be funny, if someone's getting in the way, I become like an insane Viking. Yes. Yes, you have your hills that you'll die on. You're like, this is what I care about.

Are they very passive, aggressive? Areas? Yeah. Or are they just aggressive? I think that's the Catholic. I think that's not astrology. I think that's something else. So tell me.

We're all, but we're made up of all. But let's get to this thing because you talk about it in the show, and it's really fascinating because I've had this experience of, I know exactly when it happened, but it's happened a bunch of times. When I'm in New York, I go, we sometimes tape podcasts in New York when I'm there, and we do them at Sirius XM, which is in Midtown, right across from Rockefeller Center, my old stomping ground, and I'll go into the lobby, and there have been a couple of times where, there was one time in particular where there were a bunch of young women who I think were waiting to gather to go to lunch,

and they saw me, and they came over, they said, can we get a selfie? And I said, sure. And I just started chatting with them about how's it going, what's up, and gave them a little bit of advice, probably like the advice they gave you, because I'm constantly lecturing young people. But at one point, some of the women started talking about, oh, my God, I'm so old. And I said, how old are you? And they're like, we're 28. And I, like, I wasn't eating anything, but I started choking on imaginary food. I was doing a spit take with no water.

I was like, you're 28 and you're talking about how old you are. and I forgot, that just sounds insane to me right now. But I do remember getting out of college, moving out to L.A., turning 23, then turning 24, and thinking, oh, my God, it's over for me. It's so over. And so I basically yelled at these people and said, you have no idea how young you are. But I know that, you know, your character has her 28th birthday, and it's kind of traumatic. And I think, what? What is the Saturn returns?

It's, so it's like three years, but there's like a period in it. It's different. It happens sometime between 27 and 30, and it's basically like your reckoning of like, I feel like it shakes up your life, which is why I'm interested to hear like if you can remember something from the end of your 20s. You bet I can. You bet I can. And I'm guessing it's your Saturn return because it shakes everything up and then like you go

through a breakup or you lose a job. you blah, blah, blah, whatever, something chaotic. And by the way... I've got a huge one. Can't freaking wait. But it's like, you feel like... She said that in a way like, please don't ever tell me. No, I love...

Can't fucking wait. Shut up. Go ahead. That's okay. It's okay. I was just saying it's like it happens to everyone, but it feels like it's only happening to you and then it lands you where you're meant to be. Oh.

It's kind of, but tell me your story. Oh, it's so simple, which is, uh, I'm 29. I'm a writer-producer on The Simpsons. Everything should be good, but I think, no, I'm not where I'm supposed to be. Something else is supposed to happen. It feels weird. I just was, and I remembered my agent at the time saying, well, you could get an overall deal to be at the Simpsons for five more years and you could make, you know. And I was like, no, no, I can't take that because something's supposed to happen.

Yes. One of the crazier things in show business happens, which is there's only like, there's David Letterman doesn't get the Tonight. show, and he suddenly announces, I'm leaving, which no one thought he would do. Yeah. And suddenly NBC doesn't have a late night show at 1230. They don't know what to do because this is back before the internet. So today they would look at 700. They would go TikTok account.

There'd be a million people who were viable and they'd be 900 hours of everybody. Yeah. But they don't have that. Yeah. And these jobs back then, there weren't, there were two late night talk shows. That's it. Yeah. Or just at that point, it was just one or maybe two.

And the main guy, David Letterman, has left or is leaving, announces he's leaving soon in a couple of months. They don't know what to do. So NBC says, well, we got to keep the affiliates in the line. Let's just get Lauren Michaels to decide. And that calms everybody down. Like, oh, good, Lauren Michaels, Saturday Night Live. He'll figure it out. Lauren goes looking.

It's a long story, but cut to him just in a room saying there was this writer who worked for us. who's got something. Conan O'Brien, and they're like, what? And I do an audition. I'm so loose in the audition, because I think I'll never get this. And then one thing leads to another. They say, no, it's going to be Gary Shandling.

It'll never be you. And then suddenly they go, you know, it's him. And they call me, I'm in the basement of the Simpsons, and they say, you're going to take over this massive job. There's no footage of you. everything I'd ever done was on stage there's nothing I don't even have a headshot

and everyone freaks out and that's what happened that's a pretty common Saturn return but you know that was that was how I and and that all happened the audition everything happened when I was 29

and then I am waiting to hear back and I have my 30th birthday in my L.A. apartment on Weatherly and then a couple of days after my 30th birthday. You get the call. I get the call. Yeah. That your life's changed. Saturn return, bitch. Saturn returned. What was your Saturn return? Working for you. Getting my job working for you. Oh, that's right. You were in your late 20s. I was 27. About 26 and I turned 27. And that changed. That changed my life. I mean, working for you. It's been cool. It's been okay. Wow. Ringy endorsement.

It really has. I mean, it's like everything changed once that happened. What about you, Matt? Well, mine was, yeah, I went through a really bad breakup and just took a month off work and had the same lunch every day at this bar and went home and got high and watched a James Bond movie. You showed her. That sounds real nice. She could see me now. But I started thinking, I'm going to read every Shakespeare play. And in two days, it was like, I'm just going to watch every James Bond movie.

Yeah, yeah. That was that for about a month. I looked back on it so nostalgically now, though. It was a hard time, but now I'm really fond of it. No, but it shapes you. It shaped me. I went through a bad breakup in New York that was prior to all this. And I remember it I got a Seamus Heaney poetry book.

Oh, my God. I kept it in my back pocket. And I would lie down on park benches in Manhattan and read from a poetry book. And I thought, this is who I am now. And then three days later, I was like, I got to get a job. And I went out to L.A. and worked on The Simpsons. but I, I remember thinking for a minute, this is who I am now.

You want to hear it. 28-year-old who reads famous teeny poetry. Lying down. I'm a hobo. Yeah, you are. You're like a romantic hobo. I'm a romantic hobo. The status part was that the lunch I had every day was a,

I went to an Irish pub, and I had a corn beef sandwich, a deep-fried Snickers bar, and a Guinness every single day. Oh, my God. I know. I can't believe I'm alive. That's fabulous. And that's why I stand before you the way I am here.

Yeah, incredible. Well, Rachel, it feels to me like you've had nine of these in your teens and 20s. Like you've had... Like mini ones. Well, mini ones, you've got a very big jump on a career at a very early age. I don't know. I think a lot of people in my age and younger feel like there have been a lot of like setbacks. Like it's like basically like Shiva Baby was so supposed to premiere at South Buy and then it was canceled because of COVID.

And then I was like, oh my God. my career is over because of COVID, like, when is this going to end? Whatever. Then we get back into the industry. We get to make bottoms. Bottoms comes out during the strike. And like there's, I think like. And you couldn't promote it during the strike?

Couldn't promote it during the strike. Yeah, I remember that. I remember that. But the girls on TikTok did it for us. Literally, literally shout out. Because I was like, they took the movie and ran with it. That's great. And that was amazing.

But I think like, I felt sort of a similar thing to you, which is like, basically like, I think you get, the early 20s were really chaotic. I was like, I don't know what I'm doing. By the mid-20s, I was like, not The Simpsons, but you have your stuff where you feel like, okay, I've got my thing. I know what I'm doing. And then just all of a sudden, like, something feels wrong. And you're like, I don't know what it is.

And you sort of like sit in something feeling wrong for like two years or a year, whether it be a relationship or being like, I'm not quite doing like, I'm not quite doing like, I'm doing what I want to be doing, but I'm not doing it all the way or I need whatever. And like, you have to make that leap. Like, I don't know if when you said, I'm not doing an overall deal at The Simpsons, your agent said, you're a fucking idiot. He did say that. Okay, awesome. And it's like, because you're like, I don't have the next job.

I don't know what it is. I feel something. I, for me, like, I think it was like the jump of fully stepping into a creator role on my own. It's really scary. I think I've always felt insecure. and myself as, like, a writer on my own. I just, in general, I feel like I'm a good, like, pep talker, cheerleader. I get, like, I get to-do list done, but I never really thought, like, I'm that talented.

I, in general, I think I'm just, like, more of a hard worker than I am talented. But that's, you know that that's how everybody feels. I think being hardworking is a good part of it, you know? But that's how I would have, I mean, everybody has that. Yeah. Not, I don't, that's just so common that, you know, I, I always thought that, well, I get by, because I work. Because I can outwork anybody and I do my homework. Yeah.

And then it was a long time. And look, all these years later, I still have those days. Yeah. We all have that. when you show me someone who is an artist of any kind and they have no insecurity and they have no doubt and they have no fear, I think I have no interest in seeing their art. None. Yeah.

I just have none. But it's scary and it's like there's a difference between being in someone else's thing and being a part of it and knowing like, well, if it doesn't go well, I can say, hey, I'm just the actor or like I just did. I didn't, you know what I mean? And, like, I had no control to step into a role where you're like, oh, if people hate this, they hate me. Like, you're not actually, but kind of. Like, I'm like, I, there's no, I'm like, it's like, my name, my name.

I'm like, it's me. It's, I'm naked and I wrote it. I'm, like, it's very vulnerable. And so I, like, while I was in the process of waiting to see if the show got picked up, I had, like, done the pilot. I was waiting to see if the show got picked up. HBO. You're waiting to hear from HBO. And I am like having to say no to other things. And it's really scary because I'm like, I don't know if the show is happening. I don't know if I'm good enough. I go through a breakup. I get arrested in the Cayman Islands. It's, that was my. Wait a minute. Wait a minute. And this all happened in one month. What happened in the Cayman Islands? I brought, this is on me, but I brought a CBD joy in my back. It was, I didn't even do it on purpose. it was like I had like a leftover CBD joint that I bought in a grocery store in like the back of my purse and then they really search your bag like they search your bag she's like taking out my

vibrator I'm like girl put that away in the middle of the airport like they search your bag and she was like do you have any drugs on you and I was like I do not have drugs on me so then like I was like why would I have drugs but then I didn't know CBD was also illegal so then she finds a CBD So then I got in trouble for lying about the drops. The Kerman Islands is the hub of white collar crime and they bust you for a CBD joint. It's insane. And I was it. They took my phone away.

Shout the fuck out, Claire, my assistant who's out there. You met her. She thought I was kidnapped. So they take my phone and my passport. I'm in jail for like five hours. Nothing. Claire thinks I've been kidnapped because she's calling the hotel. She's like, has anyone seen Rachel?

Some people at the hotel had seen me getting into an unmarked white van. So then Claire, which is. how they take people to jail there. What the fuck? And so then Claire's like, she's been kidnapped. So then Claire's like calling the embassy, literally. This is a good assistant because Sona, in the same situation, if they said, we've heard reports that Conan's gone, he's not at his hotel, he's been taken in a white van.

You'd be like, all right, well, let me know. In the clubs. I'm hitting the clubs. Oh, there is a joint okay? And tell me more about this joint. Did they throw that away? Can they mail it back? Oh, can they should send that back to us.

That's evidence. I might need to look at that. I should look at that. Keep him. Give me the joy. Were you scared or were you pretty confident? I was, I was scared. I think I was also just having a breakdown in my life where I was literally like, I don't have a show.

I just, I just turned down these other, like, jobs. I am like in the middle of a breakup with my boyfriend. And now I'm in jail? I was like, wait a second. I was just like, I got really freaked out where I was like, I was crying in there. And then I started telling the girl about my breakup. And it was just all, anyways, Claire called my lawyers, and they knew a lawyer on the Cayman Islands who came and got me out of jail. So it was all fine.

I just had to apologize on camera and get a mugshot. And I do have a record there. It's okay. I love it. This is, I mean, it's badass. It's badass. I wanted the picture so bad. I was like, please send me the mugshot.

They did let me put on makeup for the mugshot, which was, I thought, really sweet. I was like, I've been traveling, I'm sweating. She was like, you can go into your bag for mascara. But that was all, like, in one month. And then I got back from the Cayman Islands and the show got picked up. That's great. And then it was my birthday, my 29th birthday. So mine maybe came a little earlier than yours.

But now I just had my 30th birthday right before the show comes out. So it's very like, it feels like, I don't know, it feels like a very, like, mystical time where everything is like shifting and whatever, but I felt so out of control that whole time. And I was like, I don't know why. I just feel like I have to trust. But it's that same thing where it's like, you don't know. Well, here's what I'll tell you.

I am very confident that people are going to love your show. I am. And because I know youth culture. Uh-oh. No, no. More Dick Van Dyke references. It's really well done. Your show is really well done.

I am confident. that people are going to really like this show because I was binge watching it and really impressed. And I think you're very impressive. I thought so when we got to talk and I met you and I'm a huge fan and I'm just excited to do

to see all the things you're going to do. I really am. So just we're going to wrap it up as I want to let you go and make more cool things. But I'm a cheerleader. I'm an old dottering cheerleader I love it.

And I'm really happy for you. I'm, that really means a lot. And especially you watching all in a row means a lot to me because I know you've seen, I'm like, you thinking it's funny means a lot because you're the funniest. So. Oh, that's sweet.

Thank you. Yeah. Yeah, I thought I'd bring it sincere at the end. Thank you so much for having me. This was amazing. This was so fun. Thank you so much for doing it. This was great.

This was great. And you came in and hugged everybody and I've never touched these people. You won't even look us in the, I'm, uh, I haven't made you until today. It's nice. Yeah. We'll talk. Hey, Sona, quick question. You were talking about something that intrigued me when I entered the room, and then you quickly changed the topic.

I got the sense that you are babysitting, even though you have twin, four-year-old boys who take up a lot of. of your time. Why are you taking on a babysitting gig? What's going on? My friend has a baby who's about nine months old, almost nine months old, and they just need somebody for just a couple hours every week. What are you doing this for? For funsies. No. Can I tell you something? No, you don't get to talk on this podcast. Okay. All right. This is a podcast where white men bloviate. You be quiet. I'll handle this. Yeah. Yeah, you take over. Thank you. I'm going to pass the ball over to the other white guy.

Star Wars Here's what I don't understand I don't understand You have twin boys Yes, I do And Mikey and Charlie And they are a handful Excuse me

Did you say handfill? Yeah Handful No, handfill I changed it It's when you Never mind What were you gonna say

Handfill? What are you doing? What are you doing? What are you doing? What's your fucking problem? What are you talking about? What are you talking about? Were you going to say something really inappropriate?

Yeah. It's all coming out. It's all coming out. What? What's coming out? I mean, I'm editing it out. No, you're not going to edit it. Oh, so if I make a mistake, it stays in.

Yes. And if you become... Yes, that's the only thing I have in my life is that. I don't know what he's talking about. What I'm saying, I misspoke slightly and said handfill instead of handful. Yeah, we both made fun of you. It was fun. We had a good time.

It said funny that Conan's bleeding. into his brain. Come on. So as he ages, he's falling apart. Ha, ha. But that's not what we're going to talk about. You have twin boys who are very young. How old are they?

They're four. Four. Still, that's very young. Yeah, they are. And then you took on, you were like, hey, throw that nine-month-old my way. Well, so here's the thing. My kids go to school and then, you know,

I'm working on my second book. But that's really all I've got going on. Are you doing this just to get more material? And then, chapter 15, I got a nine-month-old. I have to say, I had twins, and we were really in it. And now I'm watching one baby, and it's not that hard. Like, babies, they eat, and they, like, you go for a walk, and then they sleep, and then you play, and it's fun. Oh, so you're shaming anyone out there who's having a hard time with one child, Sonam Obsessian?

I'm just saying, if you've had two, one after having twins is more manageable. Okay, so why don't you tell Matt? Why are you complaining? I'm not complaining. No, I know. I agree. It's fun. It's so much fun to watch a baby.

Are you getting paid? No, of course not. They're my friends. I've never known you to do anything and not demand your share. Are you paying to do it? I mean, no. I'm having fun doing it. I like hanging out with this kid.

He's a really fun baby. He's really sweet. He has a little bit of separation anxiety, which is tough. And then, you know, we're just, we're just chilling. Me and this baby like hang out. Let's be honest, when the baby's melting down and you, you're not happy with the gig. No, I don't. I'm being serious.

I don't. And I like it. And I, you know what? Maybe I'll be a nanny now. Maybe this is it for me. Maybe I'm going to quit this job and nanny. I'm not hearing of a nanny. Was this a resignation?

I'm not hearing enough. Do you got something she could sign? I basically babysat you for 12 years. Nice. You did not. We're not. I was a very emotionally mature. Adult. Wow. Even as I said it, my jaw felt, started to rot off. I agree with you that you did babysit me. And I sometimes, it was incredibly immature, I suppose. You have to coddle a genius.

Okay. What do you mean? You don't have to coddle. Do you? Yes. Okay. I don't know. You're saying you're a genius. What part of that sentence did you not understand? Do I stutter? No, whatever. Handful. Excuse me? Yes. That's a genius way of saying handful.

I don't like to say the things that everyone says. I like to invent new ways of communicating. I think you're a real handful. You've filled my hand with your problems. It's mine is, it just cuts through. I guess Joyce used a lot of language that people didn't understand. Okay. Yeah.

And then Joyce Cole Heywick. She was a broadcaster in Boston. Do you know who he's talking about? You laughed really hard. Yeah, because I'm twisting because he was talking about James Joyce and then he twisted it. Hey, you really enjoyed my humor. No, I don't enjoy your humor. By the way, if you grew up in the Boston area, shout out to Joyce Cole Heywick.

Shout out! Shout out to Joyce Cole Haywick! Shoot the noob! Shoot the noob with Joyce Colahwick! She was a big star when I was growing up in Boston. In local news? Yeah. Oh, I had no idea who she was. Oh, okay.

Yeah. Okay, we just lost all of everyone. You took us down a comedy cul-de-sac. Nope. I'm checking right now in our... You took us down a comedy handful. Whoa, look at this. Our numbers in Roxbury, Massachusetts have just gone through the roof. This doesn't go out live. I just want to say that I'm very happy that you're looking after this nine-month-old.

Yeah. And it sounds like a win-win for you. So much fun. For you, a win-win-win-win. For you, the mom and the baby. Yeah. You know, because you're a wonderful person. What?

I don't like this. Why can't you ever just accept when I'm nice to you? Call his bluff. Call his bluff. I've worked for you for so. so long. You've never just been purely sincere. That's not true. I have been sincere before. Haven't you heard it? Edward? I've seen it. Yeah. Because you're always nice to Eduardo. No, I've seen him be sincere to you. Yes. Thank you. I've told you. I've never seen it. We always, we always cut it out. He calls me later. And he insists that I

take it out. Yeah. I'm just saying sometimes when you say something nice, I hold my breath and I wait for what's next. You shouldn't wait. Because there's always a joke after. Let's do it. Well, you say that nice thing again and see if you can just let him sit in it. Okay, go ahead. I think that you'd be a great nanny. And I think that's a lucky nine-month-old and a lucky mom that's tricked you into working for free. I know your face. Oh, you know my face? Yeah, I know your face. You're not doing, no, that's not, oh, that's not doing anything. That's the worst. No, I'm being sincere. That's the worst. Where's my camera right here? I know when you're being sincere. Your face is not. You mean a great deal to me.

I really respect you. You've been a great friend and I trust you. I trust you more than I trust anyone. Oh my gosh. Who do you look like? I look like someone who just drank sour milk. Yeah. I look like an emoji that just drank sour milk.

God bless you, Sona. Yeah, I'm having fun. Yeah, and I think it's a great idea if you leave this very lucrative gig and go nanny for free. Conan O'Brien needs a friend. With Conan O'Brien, of Sessian and Matt Goorley.

Produced by me, Matt Goreley. Executive produced by Adam Sacks, Jeff Ross, and Nick Leow. Theme song by The White Stripes. Incidental music by Jimmy Vivino. Take it away, Jimmy. Our supervising producer is Aaron Blair, and our associate talent producer is Jennifer Samples.

Engineering and mixing by Eduardo Perez and Brendan Burns. Additional production support by Mars Melnik. Talent booking by Paula Davis, Gina Batista, and BrickCon. You can rate and review this show on Apple Podcasts and you might find your review read on a future episode. Got a question for Conan? Call the Team Coco hotline at 669-587-2847 and leave a message.

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