We Might Be Drunk Ep 253: Whitney Cummings

Date: October 13, 2025
Hosts: Mark Normand & Sam Morril
Guest: Whitney Cummings

Episode Overview

Theme:
This episode is a classic We Might Be Drunk hang, with comedians Sam Morril and Mark Normand joined by the irreverent and candid Whitney Cummings. The trio swaps stories about comedian life, road peeves, generational culture clashes, outrage cycles, comedy’s changing landscape, and self-destructive quirks. They riff on everything from personal vices to nostalgia, social media mobs, negative feedback, and why comedians seem primed for self-inflicted chaos.
The tone is loose, quick-witted, self-deprecating, and always teetering on the edge of controversial honesty.

Key Discussion Points & Insights

1. Cheap Habits Die Hard

• 00:06–01:30 The group confesses their lingering "cheap" habits despite success—Whitney grabs hotel matches, Mark hoards fast-food napkins, and Sam admits to pocketing hotel mints and soaps ("I haven't bought soap in 10 years" – Sam, 00:50).
• Rich people still doing broke stuff is a recurring bit.

“I love when rich people still do broke sh*t.” – Mark Normand (00:34)

2. On Fake Foods, Placebo & Suckers

• 01:27–03:40 Digression into how things like Haagen Dazs and Chilean sea bass are marketing inventions.
• Placebo effect and whether citronella candles actually work ("My dad invented them. They're fake." – Mark, quoting a lawyer, 03:11).
• Skepticism about online studies and product claims.

3. Surviving Before Comedy Paid

• 03:44–04:44 Mark shares hustling for cash via depression studies:

“Once you’ve done studies like that, any study you see, you’re like, no—that’s a bunch of people who needed $50.” – Mark (03:54)

• It’s a slice of how comics grind before making it.

4. Party Tales & Woody Allen Podcast Critique

• 04:43–07:19 Whitney on recent birthday benders ("They just kept feeding me booze," 05:06);
• The group critiques Bill Maher’s Woody Allen interview ("He talked through the whole thing. He wouldn’t let Woody talk. He sucks." – Sam, 05:52).
• Woody Allen’s legacy: Critical discussion on "Annie Hall," problematic tropes, age-gap relationships in old cinema, and the fascination with neurotic male leads.

5. Aging, Cancel Culture & Generational Slurs

• 11:31–14:09
• How society judges old celebrities differently:

"Why aren’t you giving the 85 year old guy a pass?... Ageism." – Mark (12:44)

• Reflections on language changing (Oriental, colored), Carlin’s bits, and the confusion that comes with "woke" lingo shifts.

6. Social Media Rage and Negativity

• 14:45–19:59
• Sam and Mark vent about “dead internet theory,” bots yelling at bots, and the meaninglessness of most outrage.
• Negative feedback and trolling are compared to high school bullying.

"If I was 15 and my hero was on Twitter, I'd be like, hey you, son...We’re all still in high school." – Mark (19:30)

• Whitney: "I’ll post and ghost." (15:50)
• Real world is less hostile than online:

“No one knows you. The sun is shining. Birds are chirping. It’s just on here.” – Sam (16:06)

7. Peeves Segment

a. Airline Etiquette & Parenting

• 23:40–26:06
• Whitney’s peeve: parents who let kids play video games loudly with no headphones on planes:

“Just use the headphones! …He goes, ‘She’s a baby.’ I go, ‘Yeah, but you’re not.’” – Whitney (24:13)

• Noise complaints, babies crying vs. controllable annoyances.

b. Obesity, Flights, and Comfort Wars

• 32:44–42:34
• Sam’s peeve: Being seated next to an extremely obese passenger in first class.

"This is secondhand fat." – Sam (33:39)

• Whitney reframes obesity as addiction/addictive coping, not pure choice.
• Conversation on “body positivity”—dad bods, double standards, and social empathy for different vices.

8. Comics & Vices: Addictions, Overcommitting, and Self-Sabotage

• 42:53–53:54
• The crew confesses to their current vices—Mark: overcommitting, Whitney: drinking, Sam: buying stuff for his kid.
• Whitney and Mark both like taking cabs over Ubers for human connection and street-level news:

"I divide people into who takes cabs and who doesn't." – Mark (50:08)

• Hilarious story of Mark losing his laptop in a cab and frantically chasing it around NYC (51:04–52:59).

9. Podcast Health Trends and Wellness Fads

• 54:29–56:41
• Sam’s ill-fated attempt at "health hacks" (salt in water, banana peels in the yard) leads to anecdotal lampooning of comedian wellness obsessions.

“It, like, hurt me. I almost had to go to the hospital because...I was eating so much salt.” – Sam (54:40)

• Topic: How comedians chase the next “fix,” be it health, vice, or a dopamine spike.

10. Collectibles, Wealth & Nostalgia

• 58:04–64:04
• The gang riffs on grown adults collecting toys (Labubus, Pokémon), the psychology of “flexing” with rare memorabilia or expensive oddities.

“True wealth now is buying something you don’t even want just so someone else can’t have it.” – Mark (60:04)

• Comedians admit to developing new, sometimes comical, hobbies as replacements for unhealthy coping mechanisms.
• Nostalgia for vintage cars—guest and hosts discuss personal favorites, the joy (and risk) of classic car ownership.

11. Labyrinth, Movie Nostalgia & Musicians Acting

• 68:06–74:06
• Whitney pitches "Labyrinth" (1986) as a must-watch; the group reminisces about weird children’s movies and “amusing litter” (singers starring in movies).
• Fun rapid-fire: Cher, Lady Gaga, Britney, Eminem, and Whitney Houston as stars who crossed over to acting.

"I love when they go, 'You're so famous, we don't even have a script. We'll figure it out later.'" – Whitney (71:16)

12. Work Ethic, Stand-Up, & Comedy Reps

• 77:00–79:43
• Whitney credits Louis C.K. for reinforcing a strong comedy work ethic ("That’s what it takes." – Louis, recalled by Whitney, 78:31).
• They debate why comics are shamed for "working too much" and push back:

“Why am I mentally ill for trying to be good at my job?” – Mark (79:13)

• Tension between work/life, romantic partners and the commitment stand-up demands.

Memorable Quotes & Moments

• Mark on trolls & negative feedback:
  "The narcissism to believe we never deserve any negativity ever... we're still in high school. Everyone's just trolling each other." (19:30)

• Whitney on airplane parenting:
  "I'm fine with a baby crying on a flight, but the noise from machines is controllable." (25:16)

• Sam on flights:
  "This is secondhand fat." (33:39)

• Whitney on comedian vices:
  "Our job is like understanding human nature – why don’t we have compassion for them, they’re just addicted to trolling." (19:51)

• Whitney on obsession with productivity:
  "You conflate busyness with actual productivity." (49:37)

• Mark on NYC cab wisdom:
  "Where are you from? Ukraine? Can you tell me what's going on? That's the only way." (50:20)

• Sam on online outrage:
  "I went outside and was like, here it comes... and no one knows. No one knows you." (16:06)

• Mark on the changing definition of cool:
  "I think there’s something kind of punk rock about being wholesome now." (67:02)

Notable Segments & Timestamps

• 00:06–03:40 – Wild cheap habits, hotel soap, fake food brands
• 04:43–07:19 – Woody Allen, podcast critique, age and relationships
• 11:31–14:09 – Cancel culture, aging, and changing language
• 14:45–19:59 – "Dead Internet"/trolling/negative feedback discussion
• 23:40–26:06 – Peeves: Noisy kids on flights, headphones
• 32:44–42:34 – “Secondhand fat,” body positivity, vices
• 42:53–53:54 – Addictions: Overcommitting, self-sabotage, lost laptop saga
• 54:29–56:41 – Health fads & comedian wellness trends
• 58:04–64:04 – Collectibles, cars, and nostalgia
• 68:06–74:06 – Movie recommendations, musicians in film
• 77:00–79:43 – Comedy work ethic, Louis C.K., stand-up hustle

Final Thoughts

The episode is a whirlwind of brutally honest confessions, sharp pop culture stories, and meta-observations about modern society, internet outrage, and comedian self-sabotage. Whitney Cummings seamlessly trades high-energy barbs and intimate admissions with Mark and Sam, displaying the deep camaraderie, competitiveness, and mutual understanding comics share.

“Our job is to understand human nature… So why don’t we have compassion for trolls?” – Whitney Cummings (19:51)

A highly recommended listen for comedy fans, stand-ups, and anyone craving unfiltered talk about the insecurities, distractions, and survival tactics of life in—and out—of the spotlight.