We Might Be Drunk – Ep 266: Chelsea Handler

Date: January 12, 2026
Guests: Chelsea Handler
Hosts: Sam Morril & Mark Normand

Episode Overview

In this lively episode, NYC comics Mark Normand and Sam Morril share drinks and laughs with iconic comedian, author, and former talk show host Chelsea Handler. The trio dives deep into Chelsea’s adventurous lifestyle, reflections on comedy and TV, her experience at the Critics Choice Awards, her gambling habits, her storied dating history (hello, 50 Cent), her approach to independence, and plenty of candid stories from showbiz and life on the road.

The conversation is peppered with industry insights, personal anecdotes, and uproarious banter, making it a must-listen for comedy enthusiasts and Chelsea fans alike.

Key Discussion Points & Insights

1. Chelsea Handler’s Entrance and Drink Preferences

• Chelsea jokes about being bossy with her drink order—Tanqueray, soda, salt, lots of ice—because she’s heading to Fallon after.
• “I just came from Antarctica, so I was trying to get some more [ice].” (00:10–01:10)

2. Comedy Awards and Monologues

• Chelsea is fresh off hosting the Critics Choice Awards, and the hosts congratulate her on her success.
• Sam praises a specific joke: “I love the Cialis line… the Sean Penn joke. The opener is the most important, and you nailed it.” (01:58)
• Handler confesses she enjoys roasting people at these events and preps with just a couple of rehearsals, preferring not to overthink. (09:45–11:19)

3. Philosophies on Independence and Talk Shows

• Chelsea extols freedom and not being tied down, professionally or personally:

  “My freedom is really important to me. I like the idea of not having to check in with one single fucking person about anything I do.” (12:47)

• She’s not interested in returning to traditional talk show hosting:

  “My life is a fucking dream… I can't be tied to a studio five days a week in the same city.” (11:49–12:47)

• Chelsea and the guys discuss the cyclical nature of entertainment, how podcasts have replaced talk shows, and Handler’s role as a launching pad for many comics (Chelsea Lately days). (14:30–16:12)

4. Sports Gambling, Relationships, and Vegas Stories

• Chelsea talks about betting big (“put five grand on this game”) and how gambling helps her pay attention to sports her partner is interested in:

  “I’m dating a guy who's really into gambling or football… and the only way for me to pay attention is to put money on it.” (03:48)

• Her Vegas residency ritual involves giving friends money to gamble so “I don’t force people to gamble with their own money… I never leave without what I started with. Not once has that happened.” (04:29–05:11)

5. On Writing and Comedy Careers

• Chelsea admires David Sedaris, who inspired her essay-format books. She highlights the lack of books written by women about their sexual experiences and why writing her own was groundbreaking:

  “That's what we're all doing in our 20s… for some reason we're not supposed to be talking about it.” (27:28)

• Handler details her wild book deal trajectory:

  “First book deal…I got $35,000. Then my second book, I got $2 million. And I was like, whoa.” (23:46–24:00)

6. Women, Men, and Relationship Dynamics

• The group riffs on the blurriness of gender expectations and dating, with Handler saying:

  “I feel more like a dude than I feel like a woman… I’m looking for good times, casual sex, randoms, travel, adventure…” (28:44–29:07)

• Conversation about Chelsea’s dating history, including exes like 50 Cent and Jo Koy, with fun anecdotes about being “the only one he talks about respectfully.” (32:08)

7. Comedy Origins and Industry Stories

• Chelsea recounts opening for David Tell and Zach Galifianakis—stories of rough sets and being broke, but also the kindness and camaraderie between comics.
• Encourages perseverance:

  “I like to tell that story because...your biggest failures...you never know when something's coming right around the corner.” (40:43–40:51)

• Unique moments like sleeping in Galifianakis’s hotel room and his weird promise:

  “He'd come and whisper in my ear, and he'd go, ‘I will never rape you.’” (39:04)

8. Pet Peeves Segment

• Annoyances include:
  • People being late and arriving with coffee/snacks (47:44)
  • FaceTime calls, unnecessary phone calls, and people who won’t walk into places alone (48:41)
  • No-headphones on planes, picky eaters, and the never-ending lamp vs. overhead light debate:

  “We do not get along with overhead lighting. It’s not a good look…Side lighting is the best.” (50:11)

9. The Adventure in Antarctica

• Handler recounts a whirlwind romance that kicked off with a gambling stranger and her impromptu invite to a psychedelic conference in Antarctica:

  “I sent him a link to the Antarctica trip…he wrote back, ‘I’ll see you in Antarctica,’ and bought himself a ticket…that was a hot move.” (65:04)

• Vivid stories of penguins, MDMA-fueled sights, and losing weight on the trip because of terrible food.

  “Half the people were researching psychedelics, the other half were doing them. And I was part of that group.” (66:02)

10. Touring, Comedy Scenes, and Favorite Cities

• Chelsea’s favorite venues: DC, Boston, Chicago, Seattle, Louisville, and more.
• Talks about appreciating liberal enclaves in red states and running into enthusiastic audiences everywhere. (56:56–59:16)
• Sam discusses taping his next special in Tampa, emphasizing good crowds in unexpected cities. (57:53–58:47)
• They share mutual respect for the New York/LA comedy club scene, party spots, and lament the LA nightlife “never recovering from COVID.” (55:02–55:57)

Notable Quotes & Memorable Moments

• “I love drinking. I'll have a Tanqueray with a splash of salt, soda. Who's making the drink?” —Chelsea Handler (00:23)

• “Congrats on the People's Choice Awards.”
  “It’s the Critics Choice Award.” —Sam Morril & Chelsea Handler (01:40–01:45)

• On writing a hit book:
  “I'm the only person in my family who's never gone to college, and I have seven New York Times bestsellers, so I like to fucking rub that in their faces.” —Chelsea Handler (22:27)

• On independence and relationships:
  “I'm serious about not relying on another person for anything…and I take having a good time pretty seriously.” —Chelsea Handler (13:23)

• About 50 Cent:
  “He’s not gonna have anything bad to say about me. I'm a dream for him. I was a dream.” —Chelsea Handler (32:13)

• Psychedelic Antarctica adventure:
  “This guy…wrote back, 'I'll see you in Antarctica,' and bought himself a ticket, which is like a $50,000 ticket…that was a hot move.” —Chelsea Handler (65:04)

• Comedy wisdom:
  “Your biggest failures…you never know when something's coming right around the corner.” —Chelsea Handler (40:51)

Timestamps for Major Topics

• 00:10 – Chelsea’s arrival, drink orders, pre-Fallon banter
• 01:40 – Critics Choice Awards congrats, monologue talk
• 03:48 – Chelsea and sports gambling; big Vegas stories
• 09:45 – Prepping for awards monologues & standup vs. event hosting
• 11:49 – Freedom vs. talk shows, Chelsea’s current lifestyle philosophies
• 16:08 – Chelsea Lately as a comic launching pad
• 23:46 – Career-changing book deals, inspiration from David Sedaris
• 27:28 – Writing openly as a woman, book and comedy crossover
• 32:08 – Chelsea’s dating stories, being respected by exes like 50 Cent
• 39:04 – Zach Galifianakis hotel room story
• 47:44 – Pet peeves: lateness, FaceTimes, coffee on the go
• 55:02 – NY vs LA nightlife/bar scene
• 65:04 – Chelsea’s psychedelic adventure in Antarctica
• 66:02 – Penguins, MDMA, and bad food in Antarctica
• 56:56–59:16 – Chelsea’s tour, favorite cities, on-the-road life

Chelsea’s Tour & Where to Find Her

• Tour: “High and Mighty Tour” starting Feb 13, hitting major US cities (see https://chelseahandler.com for dates)
• Podcast: Dear Chelsea - recently picked up by Netflix.

Conclusion & Vibe

Chelsea Handler is as unfiltered, sharp, and adventurous as ever. This episode is packed with industry anecdotes, honest takes on work and life, and reminders to embrace independence, risks, and good company.

For fans of comedy, drinking, and candid conversation, this episode delivers the goods—ice, soda, and a splash of salt included.