Podcast Summary: Dear Chelsea – "Got the Ick with Denis Leary"

Host: Chelsea Handler
Co-host: Katherine Law
Guest: Denis Leary
Date: March 5, 2026
Length: ~75 minutes
(Ads, intros, and outros omitted)

Episode Overview

This episode of Dear Chelsea is a lively, sharp, and heartfelt conversation with comedian, actor, and producer Denis Leary. Chelsea, Katherine, and Denis dive into topics including aging and vanity, the art of quitting vices, relationships, advice on family secrets and comedy, and the challenges of authenticity in entertainment. The tone is candid, irreverent, and packed with personal stories, humor, and real talk.

Key Discussion Points & Insights

1. Where in the World Are They? (03:25)

• Chelsea is in Helsinki, describing the city as "gloomy" and joking about the love for saunas and karaoke.
• Katherine joins from the US, and Denis comes in from a New York hotel, describing his press rounds for his show "Going Dutch."

2. Denis Leary’s Show, Aging, Drinking, and Smoking (04:08 - 15:01)

• About "Going Dutch"

  • Denis stars in "Going Dutch" (Fox, streaming on Hulu), now in Season 2.
  • “It’s a half hour comedy ... the girl who plays my daughter is amazing. Danny Pudi’s in it, and this year my girlfriend is played by Kristen Johnston, who’s brilliant.” – Denis Leary (05:00)

• Wine is Overrated

  • Both Chelsea and Denis agree wine is overrated and the rituals around it are boring.

    “Wine is a boring drink. And when people drink too much wine, especially red wine, you look like a jackass.” – Chelsea (06:09)

• Irish Drinking Upbringing

  • Denis recounts growing up Irish with whiskey and beer as staples, sharing his “two hollow legs” drinking ability.

    “Beer is not alcohol. Beer is like water … you’re just drinking beer all day.” – Denis (07:55)

• On Quitting Smoking

  • Denis describes unintentionally quitting smoking after decades:

    “I never fucking intended to quit smoking. I loved fucking smoke … [then] I went outside to smoke a cigarette, and literally at the end of that cigarette, I went, nah, I think I’m done.” (10:00)

  • Chelsea and Katherine joke he simply “got the ick” with cigarettes.

• Relationship Humor & Aging

  • Chelsea comments on older men’s appearance changes and jokes about men turning into “aging lesbians.”
  • “I think men do tend to start to look like aging lesbians at a certain point.” – Denis (15:42)
  • They riff on plastic surgery and how transparency (or lack of it) affects perceptions.

3. Sleepwalking & Celebrity Airplane Story (19:06 - 29:34)

• Sleepwalking Confessions
  • Denis reveals past sleepwalking incidents, pondering if quitting smoking stopped them.
  • Recounts a wild story: On a NYC-LA flight with the Kardashians and James Franco, Denis—while sleepwalking—attacks an air marshal with a water bottle, traumatically waking up to chaos:

    “I have him trapped in the chair … hitting him in the head … Bruce Jenner is on the floor in a karate stance ready to attack me.” – Denis (24:51)

  • Aftermath involves apologies, blow-drying pants, and being glared at by Kardashian-Jenner family and Franco.
  • Chelsea delights in the absurdity and they joke about mistaken identity.

4. Advice Segment – Family Secrets & Aging (50:43)

Caller: Elsie – DNA Reveals Secret Sibling

• Listener asks if she should tell her elderly father that his daughter is not biologically his.
• Denis: “I’m one of those people … get it out in the open.” (51:05)
• Chelsea: Disagrees, argues it would hurt the dad for no purpose, “at this stage in the game, he is her fucking father.” (52:07)
• Denis concedes: “Listen to Chelsea. She’s smarter than I am and she’s a woman.” (52:15)

5. Advice Segment – Gym Rage & Robert F. Kennedy Jr. (53:32)

Caller: Allison – Trapped in a Gym with RFK Jr.

• Allison is angry about seeing RFK Jr. at her gym, which manifests as political rage.
• Denis: Suggests confronting RFK Jr. or moving gyms. “He’s cheap and he likes showing off.” (54:16)
• Chelsea: Shares a personal horror story about buying RFK Jr.’s toxic old house.

  “The idea that this guy is in charge of the health of our country when he didn't even have a proper foundation at his house … the house is the most toxic environment ... it's cursed.” – Chelsea (56:16)

• Advice: Move gyms or tell him why (“You are the embodiment of everything that is wrong with this administration…”), but prioritize personal peace.

6. Comedy, Authenticity, and Women in Stand-Up (62:04)

Caller: Jennifer – Starting Standup at 51

• Jennifer seeks advice breaking into comedy later in life, facing cliques, and “being unhinged.”
• Denis: “Forget about [mainstream]. You just got to do what you have … just be yourself.” (63:49)
• Chelsea: Encourages her to exploit her unique perspective, especially anger about starting late, and to ignore gatekeeper comics.

  “Your take on it hasn’t been out there … if you’re unhinged and want to be original, focus on that.” (65:37)

• Katherine: Suggests TikTok over YouTube for unhinged comedy, given algorithmic reach.
• Denis, on advice from male comics: “Welcome to the future, douchebag.” (69:18)

7. Parenting, Family, and Legacies (39:23 - 44:41)

• Denis reflects on gratitude towards his immigrant parents’ support and his mother’s progressive values.

• Chelsea discusses her own upbringing, the freedom of being able to make a living as herself, and draws parallels to what modern comedians now enjoy in terms of creative liberty.

  “For me to go to her and my dad when I was 17 and go like, yeah, I think I want to be an actor ... instead they were like, okay, well, let's figure out how we could make that happen.” – Denis (39:23)

8. Notable Quotes & Memorable Moments

• “You just got the ick. I like that you got the ick from cigarettes.”
  – Chelsea (10:43)
• “When people drink too much wine, especially red wine, you look like a jackass.”
  – Chelsea (06:09)
• “I could drink like a fucking fish … my parents are both from the same village in Ireland.” – Denis (07:07)
• “Conan self-proclaimed looks like an aging lesbian.”
  – Denis (15:55)
• “I haven’t quit [masturbation].”
  – Denis (14:14)
• “Let us know if there’s anything we can do for you, Chelsea. I’m like, yeah, how about a fucking foundation?”
  – Chelsea on RFK Jr. (58:42)
• “Your take on it hasn't been out there ... focus on that.”
  – Chelsea (65:37)
• “Welcome to the future, douchebag.”
  – Denis (69:18)

Timestamps for Major Segments

• Chelsea in Helsinki, setup w/ Denis Leary – 03:25
• Talking "Going Dutch", drinking, quitting smoking – 04:08–15:01
• Sleepwalking, Kardashian plane story – 19:06–29:34
• Caller Advice: DNA family secret – 50:43
• Caller Advice: Gym with RFK Jr. – 53:32
• Caller Advice: Breaking into comedy at 51 – 62:04
• Discussion on authenticity & family influences – 39:23–44:41

Tone & Atmosphere

• Unfiltered and self-deprecating: Lots of swearing, laughter, and mutual ribbing.
• Supportive and direct: Advice is honest, never sugarcoated, and prioritizes personal well-being.
• Insightful and grounded: Reflections on family, aging, and authenticity give depth to the humor.

Conclusion

A standout episode blending Chelsea Handler's trademark wit with Denis Leary's brash candor. The episode covers the hilarious (sleepwalking carnage on a plane, hatred of wine), sincere (quitting lifelong habits, gratitude to immigrant parents), and practical (advice for navigating secrets, anger, and the comedy scene). Listeners are left with both laughs and thoughtful takeaways on how to be real, face life's absurdities, and choose self-preservation over needless drama.