Fly on the Wall with Dana Carvey & David Spade

Episode: Madonna Stories & What NOT To Say To Women
Release Date: October 13, 2025

Episode Overview

In this lively and joke-packed episode, comedians Dana Carvey and David Spade do their signature riffing on showbiz, pop culture, awkward social situations, and trending stories—with special focus on tales about Madonna, what (not) to say to women, run-ins with fame, and playful banter around current events and viral clips. Joined by regular Heather Santoro and producer Greg Holtzman, they jump from personal anecdotes to political impressions and the absurdities of modern life, all in their trademark chemistry-driven style.

Key Discussion Points & Insights

1. Awkward Encounters with Fame & Old Friends

• David’s Seattle Trip & High School Reunions (03:01–07:25)
  • David shares a story about seeing an old high school friend at a corporate gig, struggling to remember mutual acquaintances, and faking recognition out of politeness.
  • On the difficulty of remembering people:

    "So I just said, oh, yeah. She was such a handful. I think I said something very generic."
    —David Spade (06:02)

  • Dana relates meeting Paul McCartney and realizing “big moments” for one side often mean little to superstars.

2. Celebrity Encounters: Madonna Stories

• David’s Brush with Sandra Bernhard & Madonna (07:30–09:22)

  • David recounts a cold encounter with Sandra Bernhard, who was a big deal in his high school and famously friends with Madonna. He approached her as a novice standup and got little response.
  • On meeting Madonna:

    "I met your friend. Did not go well."
    —David Spade (09:22)

• Dana’s Madonna Faux Pas (09:41–11:16)

  • Dana tells his Wayne’s World/SNL Madonna story: at a party, he admired how “fit” she was, not realizing it might be perceived as diminishing her artistry.
  • After Madonna calls out the comment, Dana does a Chris Farley impression, flipping her off in jest—which she responds to playfully later.
  • Reflecting on Madonna’s legacy:

    "Madonna lit the match…they copied Madonna."
    —Dana Carvey (11:17)

3. What (Not) to Say to Women (11:41–13:12)

• Dana and David riff on backhanded or clueless compliments like "sturdy," "healthy," "strong," and "bulking up for something." They agree these are all dangerous territory when speaking to women.

  • "Healthy is the worst thing you could say to anyone."
    —David Spade (12:01)

• Heather offers:

  "You look fantastic." (12:37)

• They acknowledge it’s often reflex to focus on appearance, but just giving a genuine compliment is always safest.

4. Political Satire & Current Events

• Middle East Peace Deal & Trump Impressions (15:52–18:21)

  • Dana does Obama and Trump impressions, poking fun at political credit-claiming over peace deals.
  • David:

    "He doesn't like pauses. You're right.” (17:58)

• Sen. John Kennedy’s Taylor Swift Lyric Quote in Congress (20:20–21:26)

  • Heather recites Senator Kennedy's reading of Taylor Swift lyrics decontextualized in a congressional hearing for comedic effect.
  • Dana and David lampoon his grandstanding and exaggerated performance style.

  • “Whatever your side… you gotta laugh.”
    —Dana Carvey (23:19)

5. Viral & Oddball News Stories

a. Saggy Pants Crackdown (23:36–26:24)

• Teens in Tennessee jailed for indecent exposure for sagging pants.
• Dana explains the origin: it comes from prisons, where belts are confiscated.
• On the fashion trend:

  “You look shuffly… but all fashion, like, it doesn't matter. If you can handle it, do it.”
  —David Spade (25:41)

b. Viral Woman Returns $2,000 Gift (27:06–29:57)

• A dating story where a woman sends back a $2k birthday gift as not meeting her “standards,” sparking debates about values and entitlement.
• Dana:

  “2,000 in cash would feel like 20,000 because everything is digital… you never really see or feel your money.” (28:01)

• Reflection on social media and “Kardashian effect” warping gift expectations.

c. LeBron James/Hennessy Lawsuit (30:11–31:40)

• A fan sues LeBron for implying he might retire, causing them to overpay for tickets, only for him to announce a brand partnership.
• Jokes about the scope of lawsuits and LeBron’s athletic longevity.
• “No one wants under millions. Why does anyone sue anyone?”
  —David Spade (31:29)

d. “Woman from the Nation of Terenza” at JFK (33:57–36:19)

• A wild news story: a woman at JFK presents a passport from a non-existent country; vanishes on security cameras.
• The hosts debate if it’s a hoax, a sign of AI-powered misinformation, or "alien" activity.

• “AI don’t believe it. Smart, right?”
  —Dana Carvey (35:46)

e. AI Laser Weapons & Firefighting Policies (42:04–50:26)

• Playful riffing on the Pentagon’s AI-controlled energy weapons and concerns about AI autonomy.
• Discussion of the California wildfire, firefighting staffing, and resource allocation controversies.

• "We could put more money toward that. It would be great."
  —David Spade (51:12)

Memorable Quotes & Moments

• On meeting Madonna (Dana):

  “I said the thing I admire about you most—how fit you are... And she basically kind of said, ‘the thing you admire about me is how fit I am? I'm an artist, you know what I mean?’" (10:06)

• Generic small talk pitfalls (David):

  “Let me tell you something that are not compliments to women. Sturdy. You look strong. You look healthy... are you bulking up for something?” (12:01)

• On social media & cash impulses:

  “Everything is digital, electronic, you never really see or feel your... So when you have money in your hand... there’s something better about that.”
  —Dana Carvey (28:01)

• UFO/AI suspicion:

  "Pretty soon, they can do anything with AI. They could say a criminal will get off robbing a bank. They show the video, they go, that could be AI, it's not me.”
  —David Spade (35:49)

Timestamps for Key Segments

• Show's Start and Initial Banter — 02:21
• David’s Seattle/Corporate Gig & Old Friends — 03:01–07:25
• Sandra Bernhard, Madonna & Fame Disconnect — 07:30–09:22
• Wayne's World & Madonna Story — 09:41–11:16
• What NOT to Say to Women — 11:41–13:12
• Political Satire: Middle East Peace Deal — 15:52–18:21
• Senator John Kennedy Reads Taylor Swift Lyrics — 20:20–21:26
• Saggy Pants / Fashion Trends — 23:36–26:24
• $2,000 Gift Viral Story — 27:06–29:57
• LeBron James & Hennessy Lawsuit — 30:11–31:40
• Nation of Terenza / Passport Story — 33:57–36:19
• AI Weapons & Firefighting Funding — 42:04–51:12
• Boston Slide Cop Test / Playground Dangers — 54:26–56:39

Notable Segments Not to Miss

• Impressions showcase: Dana’s Obama and Trump (17:09–18:21), plus Senator Kennedy and their interplay on political absurdity.
• Listener/YouTube comment banter: (56:42–57:32) — playful self-deprecation about recurring jokes and wardrobe.

Conclusion

This episode is a classic “Fly on the Wall” blend: equal parts personal confession, punchlines, absurd news, showbiz reflection, and political lampooning. Dana and David’s laughter is infectious, effortlessly swinging from Madonna-lore to what makes a bad compliment, faux pas with celebrities, and the never-ending weirdness of viral news. The episode is a strong reminder of why their chemistry and timing keep listeners returning for more.