Conan O’Brien Needs A Friend — Rachel Sennott (November 10, 2025)

Podcast: Conan O'Brien Needs A Friend
Host: Conan O'Brien (with Sona Movsesian & Matt Gourley)
Guest: Rachel Sennott
Theme: Navigating creative careers, the existential turmoil of the late 20s, creative vulnerability, East vs. West Coast culture, and generational shifts in comedy and media.

Episode Overview

In this episode, Conan is joined by actress, comedian, and writer Rachel Sennott, known for the film Bottoms and the new HBO series I Love L.A., which she co-created. The conversation moves fluidly between lighthearted banter and deeper reflections on creative ambition, generational anxieties, and adapting personal stories into comedy. Rachel and Conan draw parallels between their own career leaps in their late twenties, discussing anxiety, impostor syndrome, and the unpredictable moments that define an artist's life.

Key Discussion Points & Insights

1. Opening Banter: High School Panic & Staying Relevant

(02:01 – 10:49)

• The team discusses Eduardo’s impending “Career Day” talk at a high school, joking about how to connect with Gen Z.
  • Conan: "No one is tighter with the high school community than I am. Especially in Rancho Cucamonga. You are speaking my language." (02:56)
• Playful confusion about current teen catchphrases (like "six, seven") and which podcast guests would resonate with younger kids.
• Acknowledgment that pop culture knowledge is shifting fast, leading to jokes about Conan’s “out-of-date” references.
  • Rachel: (jokes) "Do you think if he shows them (your Hot Ones clip), they'll be like, 'Who is this guy?' Or do you think they'll be like, 'Oh, he seems...'" (06:38)

2. Meeting Rachel Sennott: Stand-up, Comedy, and Mutual Admiration

(10:49 – 14:54)

• Rachel recalls their previous encounter at a charity event, joking about Conan pocketing donations.
  • Rachel: "They were upset, and you said, Too bad. Too bad, bitches. But other than that, it was lovely." (11:24)
• Conan watched Bottoms twice and binged five episodes of I Love L.A. in one night, leading to modesty and mutual compliments.

3. Relocating to L.A.: Culture Shock & Comparing Coasts

(15:26 – 19:42)

• Rachel and Conan connect over both being transplants with deep East Coast roots.
• Rachel discusses East/West Coast discomfort:
  • “Everyone was like, you talk so fast and you’re really stressed... I need to get on your guys' level but I can’t.” (17:09)
• Sona shares reverse culture shock stories when visiting NYC.

4. L.A. & New York: Stereotypes vs. Realities

(18:42 – 20:10)

• Conan and Rachel discuss how the stereotypes about each coast rarely capture the evolving reality, especially for creative people and artists.
  • Conan: “References can change, but the fundamental elements don't change… It's horrifying to come out to LA when you grow up on that other coast. And I was horrified.” (16:48)

5. Writing, Acting, and the Hustle: Wearing Many Hats

(24:04 – 29:59)

• Rachel breaks down her journey: starting with small web series, writing Bottoms, and now helming I Love L.A.
• Explains the chaos of showrunning, acting, and directing simultaneously—how her control-freak nature is both a challenge and a creative engine.
  • Rachel: "I kind of have, in a way... I'm kind of either stressed or stupid or both. It's one of the... there’s like two sides to me." (24:51)
• The complexity of sex scenes on the show, telling stories about relationships through comedy, and the surreal experience of being both actor and showrunner for intimate scenes.

6. Saturn Return, Generational Anxiety, & Career Inflection Points

(37:27 – 53:32)

• Rachel introduces Conan and Sona to the concept of a "Saturn Return"—the tumultuous period (ages 27-30) marking personal upheaval and growth.
  • The group shares transformative late-20s stories—career jumps, breakups, and life pivots.
  • Conan: "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." (41:57)
• Rachel recounts her own recent Saturn Return: the rollercoaster of COVID canceling festival premieres, career anxiety, a breakup, and getting arrested in the Cayman Islands for accidentally bringing a CBD joint.
  • Rachel: "I got really freaked out where I was like...I’m in the middle of a breakup, and now I'm in jail." (52:27)

7. Creative Vulnerability, Impostor Syndrome, & Hard Work

(48:49 – 54:00)

• Rachel opens up about fear and impostor syndrome, particularly when stepping into the creator/showrunner role.
  • The difference between being “just an actor” and putting your name on the whole project.
  • Rachel: "I think I'm just more of a hard worker than I am talented." (48:49)
  • Conan: “When you show me someone who is an artist of any kind and they have no insecurity...I have no interest in seeing their art. None.” (49:14)

8. Portraying Influencer Culture & The Pace of the Internet

(32:50 – 36:48)

• Rachel explains the challenges and intentions of depicting “influencer” businesses on TV without it feeling dated or cringe, likening their approach to Entourage for internet it-girls.
• Discussion of the difficulty in capturing the always-mutating nature of online culture and how they built a “fictional internet” for the show.
  • Rachel: “It moves and lives and breathes in the same way...But we don’t reference anything specific.” (34:26)
• Conan brings up the Dick Van Dyke Show approach—depicting the world around a job, not the job itself.

9. Astrology Side-quest: Aries, Catholic Guilt, and Intensity

(37:30 – 39:43)

• Rachel quizzes Conan on his star sign; Conan’s an Aries, described as intense and particular.
  • Conan: "If someone's getting in the way, I become like an insane Viking." (39:08)
• Discussion of how astrology (and Irish/Italian Catholic upbringing) might explain their approach to control, work, and outbursts.

10. Mutual Validation & Closing Compliments

(54:00 – 55:10)

• Heartfelt back-and-forth about how much it means to be validated by each other.
  • Conan: “I am confident that people are gonna love your show...I was binge watching it and really impressed.” (54:00)
  • Rachel: “You thinking it’s funny means a lot because you’re the funniest.” (55:03)

Notable Quotes & Memorable Moments

• Rachel Sennott (on impostor syndrome):
  “I think I'm just more of a hard worker than I am talented.” (48:49)

• Conan O'Brien (on insecurity in art):
  “When you show me someone...who has no insecurity and they have no doubt and they have no fear, I think, I have no interest in seeing their art.” (49:14)

• Rachel Sennott (after revealing her arrest):
  “They did let me put on makeup for the mug shot, which was, I thought, really sweet.” (53:10)

• Conan (on creative breakthroughs):
  “References can change, but the fundamental elements don't change... It's horrifying to come out to LA when you grow up on that other coast. And I was horrified.” (16:48)

• Conan describing Saturn Return:
  "I'm 29, I'm a writer-producer on The Simpsons. ...And I was like, no, no, I can't take that. Something’s supposed to happen. ...Then I get the call: You’re going to take over this massive job." (41:57–43:08)

• Matt Gourley (on post-breakup nostalgia):
  “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.” (44:56)

Timestamps for Important Segments

• High School Panic / Connecting with Gen Z – 02:01–10:49
• Meeting Rachel — Previous Charity Encounter – 10:49–12:40
• Coast Culture Shock – 15:26–19:42
• Artist Anxiety & Control – 24:04–29:59
• Sexuality & Comedy in Writing TV – 24:49–28:10
• Depicting Influencer Business – 32:50–36:48
• Saturn Return, Career Upheaval – 37:27–54:00
• Breakups, Arrests, and Growth – 52:27–53:32
• Creative Vulnerability – 48:49–54:00
• Closing Compliments and Affirmation – 54:00–55:10

Tone & Style

• Playful, candid, and quick-witted, with a mix of sincere vulnerability and relentless joking.
• Rachel blends comedian’s brio with genuine self-doubt and insight; Conan oscillates between self-mockery, probing curiosity, and unexpected emotional candor.

Summary for Non-Listeners

This episode is equally funny and revealing, bringing out both the fast-paced banter and the existential anxieties that come with creative careers. Rachel Sennott is a dynamic, self-effacing guest who delves into the reality of creating modern comedy amidst generational and technological change. Both she and Conan reflect on pivotal, terrifying career moments in their late 20s—what Rachel calls the "Saturn Return"—and the mix of doubt, hard work, and dumb luck involved.

The discussion bridges the micro (awkward high school assemblies, mugshots in the Cayman Islands) and the macro (what it takes to leap into a creative life, why insecurity makes for better art). The episode is a must-listen for anyone feeling stuck, for those wondering how comic creators thread personal chaos into public laughs, and for anyone ready to laugh about the darkest, weirdest moments of stepping outside your comfort zone.