So True with Caleb Hearon: “Rachel Sennott is Popping In”

Podcast: So True with Caleb Hearon
Episode: Rachel Sennott is Popping In
Release Date: September 25, 2025
Host: Caleb Hearon
Guest: Rachel Sennott

Episode Overview

This episode features comedian, writer, actor, and showrunner Rachel Sennott in a lively, freewheeling conversation with host Caleb Hearon. The two friends, both rising stars in the comedy and entertainment world, reminisce about bonding on a film set in Toronto, swap stories about life in LA, navigating the entertainment industry, car accidents, and the chaos (and beauty) of running a TV writers’ room. Rachel discusses her new HBO show “I Love LA,” the creative journey behind it, and lessons learned from showrunning for the first time.

The tone is candid, irreverent, and warm—marked by heartfelt admissions, silly bits, and earnest reflections on finding boundaries, surviving toxic relationships, and the comfort of female friendship.

Key Discussion Points and Insights

1. Film Set Memories & Showbiz Realities

• Bonding in Toronto: Caleb and Rachel reminisce about shooting a film together in Toronto and how their friendship solidified (“It’s where I fell in love with you.” – Caleb, [01:48]).
• Expectations vs. Reality: They laugh about people expecting comedy from their movie “I Used to Be Funny” (formerly “Brooke and Sam”), only to find it devastatingly emotional ([02:06]–[02:44]).
• Behind-the-Scenes Stories: They describe “crying days” on set, and the unique experience of ensemble acting (Rachel: “There was, of course, the famous crying day.” [02:55]).

2. The Joy of 'Popping In' (and Out) on Sets

• Both agree that playing small roles or visiting sets briefly is the dream (“Popping in is the dream.” – Caleb, [06:59]) rather than doing exhausting long shoots.

3. Relocating & Life in Los Angeles

• Moving to LA: Caleb and Rachel share their experiences moving to LA during COVID. Both have funny and harrowing stories, including Rachel’s rental car disaster and run-ins with North Hollywood’s “pop-up” apartments ([11:24], [11:55]).
• Rachel on LA Culture: Describes being “a knit poncho girl” fantasizing about adopting small-town fashions, and grapples with the realities of living somewhere past the “honeymoon” period ([08:56]–[09:01]).

4. Rachel’s New HBO Show: I Love LA

• Title Origin: Named after the iconic Randy Newman song, which holds personal memories for both of them ([09:16]–[09:21]).
• Show Themes: Rachel discusses moving to LA for a sitcom gig and the reality of building a new life, with all its chaos and accidents ([10:20]–[13:24]).
• Car Accidents as LA Rite of Passage: Both swap stories about their various car accidents in LA. Rachel humorously admits to a high number: “Is yours north of 20?... No. No, no" ([13:47]–[13:55]).
  • Quote: “You’re a beautiful, sweet girl in LA who works in entertainment. They should have a subsidy for you, like, twice a year. Some network should pay for your car accident.” – Caleb ([16:01])

5. Interpersonal Mishaps and Female Empathy

• Rachel and Caleb tell stories about car accidents leading to emotional, almost cinematic connections with strangers (crying together after being hit, making dinner plans with people they crashed into).
  • Quote: “If only women and gay people got into conflict. Because when two women are crying, it’s like, no one’s at fault.” – Caleb ([25:42])

6. Rachel’s High School Theater Origins

• Caleb surprises Rachel with an old photo from her high school performance as Madame Thénardier in Les Mis.
• Rachel shares that wearing a corset in the show helped her “connect with [her] sexuality” and completely shifted her social life ([33:09]).

7. Showrunning: The Reality vs. the Myth

• Learning on the Job: Rachel, a first-time showrunner, describes the steep learning curve—Googling job titles, making it up as she goes, and borrowing phrases from more experienced showrunners ([44:10]–[45:54]).
• Writers Room Vulnerabilities: She discusses the terror and humility of pitching ideas out loud, and how crucial a collaborative, ego-free environment is ([36:40]–[40:27]).
  • Quote: “I feel like I’m running an insurance company sometimes…I literally would Google stuff and be like, what is this?” – Rachel ([44:18])
• The Joy of Collaboration: They celebrate the collective genius of writers’ rooms and the magic of hearing characters come to life through actors ([41:38]–[43:07]).

8. What's “So True” to Rachel?

• Necessary Toxic Relationships: Rachel believes everyone needs a toxic relationship or friendship to develop real boundaries.
  • Quote: “Everybody needs a toxic—in a fun way—relationship where they get dragged through the dirt. …If you don’t have that, maybe a really bad friendship to shape your personality.” – Rachel ([53:35])
• Growing Through Hard Times: Caleb and Rachel reflect on how, with enough “data” (life experience), people learn to handle hard times and recover more quickly.

9. Boundaries, Rules, and Learning to Break Them

• Rachel humorously lists her self-imposed rules (bone broth, meditation, weeknight restrictions) and notes how, with maturity, you can safely break your own boundaries, as long as you plan for the consequences (i.e., “milk nights” and accepting the consequences for your stomach) ([55:16]–[57:23]).

10. Game Segment: Rachel, True or False?

• Caleb quizzes Rachel on rapid-fire true-or-false questions, with a prize on the line. Rachel’s answers are energetic and comedic (“Whoa, whoa, whoa, whoa, whoa” – Rachel, [60:17]).

11. Plans & The Reality of Friendship in Entertainment

• Rachel looks forward to moving, rekindling relationships, and “making good on promises” after the show’s production.
• Both reflect on how, as busy creators, they only get quality time by scheduling it as work—or a podcast ([64:49]–[64:56]).

Notable Quotes & Memorable Moments

• “Popping in is the dream. I come in for two days. I’m a fucking delight. Then you leave.” – Caleb ([07:12])
• “You choose to live here all the time?” – Rachel, on visiting small towns ([08:08])
• “Is yours north of 20?” – Caleb to Rachel on car accidents ([13:54])
• “Why did you choose I Love LA for the title?” – Caleb ([10:17])
• “I cried. I literally stepped outside the parking garage in Long Beach and I was like—I was seeing colors again for the first time.” – Caleb, on getting vaccinated ([11:00])
• “I think it needs to be like—tested against something also.” – Rachel, on boundaries ([54:43])
• “Girls are going through a lot. We’re juggling a lot.” – Rachel ([26:52])

Timestamps for Key Segments

• [01:30] – Reuniting and Toronto film set memories
• [05:22] – On wanting credit for background crying (film acting jokes)
• [06:58] – The Dream of “Popping In” on TV/Film shoots
• [09:02] – Discussion of Rachel’s New HBO Show, "I Love LA"
• [13:24] – Swap stories about car accidents in LA
• [17:00] – Improv show meet-cute crash story
• [21:15] – Rachel recounts being (lightly) hit by a car as a pedestrian
• [25:42] – The peace of all-women accidents: “When two women are crying, it’s like, no one’s at fault.”
• [33:09] – Rachel on Les Mis and discovering body/sexuality
• [36:40] – First-time showrunner, learning curve and writers’ room lessons
• [41:00] – What Rachel hopes "I Love LA" gives viewers (ritual, escape, fun)
• [53:35] – Rachel’s "So True": The necessity of toxic relationships and real boundaries
• [60:12] – True or False game segment
• [62:30] – Rachel on post-production life and reconnecting
• [64:49] – Final reflections on friendship and making time

Tone & Style

The conversation is breezy, vulnerable, and frequently derails into bits, impressions, and self-deprecation. Caleb and Rachel blend industry-insider humor, heartfelt confessions, and relatable millennial spirals about adulting, therapy, and the LA lifestyle. Their exchanges are fast-paced, friendly, and always undercut by a sense of camaraderie and empathy.

Final Thoughts

For listeners, this episode offers a hilarious and insightful window into life as a young creative in Hollywood. Whether you’re struggling with your own boundaries, dreaming of “popping in” on someone else’s fun, or just want to laugh about the trauma of car accidents and “milk nights,” Caleb and Rachel deliver—sharing lessons from both their successes and their (many) mishaps.
The anticipation for Rachel Sennott’s HBO show “I Love LA” is amped up by her candid, behind-the-scenes stories of learning on the fly, her affection for her cast, and her conviction that chaos (and female friendship) breeds the best kind of TV.

For New Listeners

Jump in anywhere—this episode’s laugh-out-loud stories and thoughtful moments will resonate even if you’re new to the pod or to either comedian’s work. Caleb and Rachel’s chemistry is so fun and real, you’ll feel like you’re popping in on old friends.