Overview of Ep 266: Chelsea Handler
Episode 266 of the podcast (hosts Sam Morril & Mark Normand) features Chelsea Handler in a freewheeling conversation covering her comedy career, writing, relationships, touring, a dramatic Antarctica trip, and behind-the-scenes stories from awards shows and TV. The talk mixes anecdotes (romantic, professional and absurd), practical thoughts on creativity and freedom, recurring peeves, and plugs for Chelsea’s tour and podcast.
Main topics covered
- Chelsea’s recent awards monologue (Critics’ Choice): rehearsal process, flexibility for last‑minute changes, and the experience of performing to set the tone for big events.
- On hosting/talk shows: why she’s currently uninterested in a daily studio talk show (values freedom, wanders a lot), but thinks the old “Chelsea Lately” format could be revived by someone.
- Career reflections: how Chelsea launched other comics’ careers via Chelsea Lately, her writing career (7 New York Times bestsellers), and the surprising economics of book deals (first book advance ~$35k; second ~$2M).
- Touring and stand-up: upcoming tour (“High and Mighty”—starts Feb 13 in D.C.), special taping in Tampa (adding dates), thoughts on performing and rehearsing material.
- Personal life & relationships: dating anecdotes (50 Cent, Tom Rhodes, other partners), preference for independence, and funny/awkward relationship moments.
- Gambling habits: enjoys blackjack and betting on sports; uses gambling to engage with sports she’d otherwise ignore.
- Antarctica story: attended a psychedelic conference in Antarctica, met a man there who flew in to join her trip; they began dating afterward—recounts the breathtaking landscape and surreal experience.
- Comedy culture & industry: roasts, bombed sets (Montreal), advice about perseverance and the unpredictable nature of show business; podcasts as modern talk-show/radio analogues.
- Peeves and cultural complaints: late people with coffee/snacks, unnecessary pre-meeting phone calls and FaceTimes, eating in bed, bad hotel lighting, open‑carry concerns at venues.
- Lighthearted bits: tasting Malört, scratch‑off gag, opening gifts and merch.
Notable anecdotes & insights
- Critics’ Choice monologue: Chelsea rehearsed the monologue only a few times; last-minute audience changes (Timothée Chalamet, Leonardo DiCaprio) required flexibility.
- Rob Reiner: Chelsea shared fond memories and praised him as a kind, talented figure (referred to his range—Misery to The Princess Bride).
- Book trajectory: first book sold for a modest advance then became an international hit; second deal jumped to $2M—emphasizes how writing has been a lucrative, unexpected part of her career.
- Chelsea Lately: credited as a launch pad for many comedians (Fortune Feimster, Bobby Lee, Whitney Cummings, etc.).
- Antarctica romance: met someone in Vegas, later connected around an Antarctica psychedelic trip; he bought an expensive ticket to meet her there—romantic/absurd opener to a relationship.
- On freedom: Chelsea values not being tied to a studio/boss; prefers touring and the autonomy of podcasting/standup.
Memorable quotes (paraphrased)
- “I like the idea of not having to check in with one single fucking person about anything I do.”
- On standup: “The opener’s the most important joke, and you nailed it.”
- On careers and failure: big failures can be immediately followed by big breaks—don’t assume one bad gig is the end.
Practical details & plugs
- Tour: “High and Mighty Tour” — starts Feb 13 in Washington, D.C.; many dates listed across the U.S.; Chelsea is taping a special in Tampa (adding a third show Feb 26).
- Tour website: ChelseaHandler.com (for dates/tickets).
- Podcast: Chelsea’s podcast (mentioned as “Dear Chelsea”) and note that Netflix purchased her podcast (she references podcasts becoming the “talk shows” of the future).
- Sponsors read during episode: Shopify, Stouffer’s, and Red Circle (ad read for Red Circle toward the end).
Takeaways for listeners
- Chelsea emphasizes artistic independence: touring, writing, and podcasting give her more freedom than a traditional talk show.
- The comedy business is unpredictable—early failures don’t preclude later success.
- Chelsea’s career demonstrates crossover between standup, TV, books, and podcasting; diversifying creative outlets can be lucrative.
- If you want to see Chelsea live, check ChelseaHandler.com for dates and buy tickets early (special taping in Tampa was being expanded).
Quick episode highlights (easy scan)
- Opening banter & drinks; Critics’ Choice monologue talk
- Rob Reiner memories
- Gambling and Vegas habits; blackjack approach
- Chelsea’s book deals and writing path
- Dating stories: 50 Cent, Tom Rhodes, new boyfriend (met via Antarctica trip)
- Antarctica trip: psychedelic conference, penguins, kayaking, Drake Passage
- Comedy career reflections: bombed gigs, Montreal, mentorship influence
- Peeves list (phone calls, FaceTime, eating in bed, lighting)
- Tour plug + special taping (Tampa), ChelseaHandler.com
- Sponsors: Shopify, Stouffer’s, Red Circle
If you want a single action: visit ChelseaHandler.com for tour dates and ticket info (she’s actively adding shows and taping a special).