Fly on the Wall with Dana Carvey and David Spade

Episode: Charlie Sheen Bets On Himself And Keeps WINNING!

Date: October 2, 2025
Guest: Charlie Sheen
Hosts: Dana Carvey & David Spade

Overview

In this vibrant episode, comic legends Dana Carvey and David Spade catch up with the always-controversial, endlessly entertaining Charlie Sheen. Taking listeners on a whirlwind journey through Sheen’s storied Hollywood career, the trio covers early stardom, wild years, iconic catchphrases, sitcom syndication, memorable near-misses, and what it means to “bet on yourself.” Along the way: plenty of laughs, never-told-before stories, career reflections, and heartfelt moments about family and fame.

Key Discussion Points & Insights

1. Charlie & Emilio: Growing Up Estevez/Sheen

• Sheen’s Early Hollywood: Dana and David marvel at the unprecedented run Charlie and his brother Emilio Estevez had as young stars ("that has never happened in history. You both were like children...becoming movie stars like that." – David, 06:56).
• Home Movies & Childhood: Sheen reminisces about their “funky and cool” middle-class upbringing (33:03) and filming Super 8s with friends like Sean Penn and Rob Lowe.
• Emilio Cameo: Emilio makes a brief, unexpected appearance via Charlie's phone, prompting effusive praise for both siblings’ early careers (06:01).
• Friend Group: "We were all middle class... nobody was rolling, nobody was driving a fancy car." (Charlie, 33:28).

2. Charlie’s Iconic Roles and the Hollywood Machine

• Breakout Projects: The trio covers Sheen’s legendary filmography—Ferris Bueller, Platoon, Wall Street, Hot Shots, Major League, and the monster sitcom Two and a Half Men ("It's kind of unparalleled how many movies he's made... and then he got into all the funny movies," – Dana, 04:17).
• Sitcom Days & Syndication: Dana explains syndication’s high-stakes history; Charlie elaborates on the unique "10/90 deal" with Anger Management, how he bet on himself, and why that production model was so intense (“It was a 1090...You gamble. And Charlie gambled and won again. And he got 100 out of it, right?” – Dana, 24:32).
• Walking Away from Huge Success: Charlie admits to actively trying to price himself out of Two and a Half Men as his passion waned and personal complications grew ("I was waiting for them to say, 'All right, we're done.' ...I completely lost a passion" – Charlie, 28:09).

3. “Winning” and The Tiger Blood Era—Comedy or Breakdown?

• Comedy in Crisis: Dana and David suggest that Charlie’s infamous “Tiger Blood” rants were more stand-up act than meltdown.
  • “It's not the rantings of a madman, it's a comedian unleashed, you know?” – David (09:13)
  • Charlie confesses many now-famous lines (“winning,” “pick a fight with a warlock”) were inspired by athlete Brian Wilson:
    “All that shit was borrowed. That T-shirt you’re wearing, not my stuff. I just had to roll with it.” – Charlie (13:49)
• Media Concern & Authenticity: The hosts critique the faux-concern of talk show hosts and journalists (“You’re like, I have $100 million. Is it horrible right now? … Do we envy you or do we feel sorry?” – Dana, 11:26).
• Lessons: Charlie wonders aloud what would happen if he’d told the media he wasn’t okay: “How do you plan on helping me?...Do you have a guest room?” (Charlie, 12:19)
• Notable Exchange:
  • David: “Are you on drugs?”
  • Charlie: “Yes, I'm on a drug. It’s called Charlie Sheen.” (09:22)

4. Hollywood “Almosts”—Roles That Got Away

• Regret List:
  • White Men Can’t Jump (originally for Woody Harrelson’s role)
  • Indecent Proposal
  • Karate Kid ("That bear ate me twice!"—Charlie on missing Karate Kid due to prior commitment to Grizzly, 39:47)
• Crucial Fatherly Advice: Martin Sheen guided Charlie to honor commitments instead of chasing superstardom (“Being a man of your word is going to sell you further than one big movie” – Charlie, 39:52).
• Reflection: “I kept waiting for Woody to send me some flowers and thank me for advancing his career like I did.” (Charlie, 37:21)

5. Art of the Straight Man & Comedic Influences

• Sitcom DNA: Charlie discusses borrowing from Leslie Nielsen (Hot Shots) and Ted Danson (Cheers) to master the “straight man” style on Two and a Half Men.
  • “And some of that...I was borrowing, you know, a lot of stuff from Leslie Nielsen.” (Charlie, 43:38)
  • “It's hard to be a funny straight man like Andy Griffith was to Barnes.” – Dana, 44:27
• Praise from Peers: “To get comedic compliments from you guys is really badass.” – Charlie, 44:32

6. Collectibles, Fame, and Childhood Dreams

• Baseball Memorabilia: At one time, Charlie was a top collector of rare baseball artifacts—Babe Ruth’s coat, Ted Williams jersey.
  • “If I don’t have room on a wall for this...I need to recirculate a lot of these artifacts.” (49:16)
• Letting Go: Eventually, Sheen sold it all, realizing the joy from sharing these treasures (“...just let others enjoy them.” 50:16)
• Nostalgia & Competition: Spade and Charlie riff on how childlike passions—like collecting or friendly banter—persist despite adult fame and fortune.

7. Reflections On Talent, Collaboration, And Hollywood Friends

• On Working with Legends: Charlie remembers being “distracted” watching his dad, Michael Douglas, and James Spader act in Wall Street:
  • “You become an audience member and then wait—but you’re in the scene and shit, it’s my line.” (Charlie, 41:01)
  • Michael J. Fox: “Other level talent...tons flying off him and took it over to that thing [Two and a Half Men]” (Charlie, 42:23)
• Comedic Heavyweights: Charlie’s admiration for Nic Cage's zaniness and courage as an actor (“...rooted somewhere outside of what us mortals can grasp. It’s an insane and beautiful mashup.” – Charlie, 53:54)

8. Hollywood Circles: Tom Cruise, Sean Penn, Rob Lowe

• Early Encounters with Icons:
  • Cruise: “In my mind, I added a Z...I thought he was a Mexican or a Spaniard, right?...There’s something going on here for sure.” (Charlie, 55:19)
  • Emilio & Tom: “Auditioning for The Outsiders at the same time...they’ve been great friends ever since.” (Charlie, 56:00)
• Styles & Legacies: Hosts and Sheen marvel at Cruise’s willingness to do his own stunts, his emotional acting, and musings on whether he’ll return to dramatic fare (“Do you think at some point he's going to want to get back to like a Magnolia?” – Charlie, 56:43)

9. Notable & Hilarious Quotes

• Charlie on Winning: “Are you bipolar? I’m by-winning. I win here, I win there. Now what? This is funny. They picked a fight with a warlock.” – David recounts, 09:42
• Charlie on Comedy: “I've never heard it described as...a comedian unleashed.” – 09:17
• Charlie on collectables: “If I don’t have room...for this...I need to recirculate a lot of these artifacts and antiques and just let others enjoy them.” (49:16)
• Dana on Michael J. Fox (impression, 65:47): “Hey, Sarge. Hey, you gotta give me a minute on this here, Sarge. Oh, Christ. She’s just a farm girl, Sarge, what are we doing here exactly?”

Memorable Moments & Banter

• Chair Bonding at the Fight: Charlie and David recount nervously wondering if precariously rigged overhead lights might fall on them at a boxing match.
  • “If that breaks loose, we’re clearly in the crush zone. Right? Are you cool if I’m the last guy...you interact with? ...I’m okay with it being you, too.” – Charlie, 64:02
• On Faux Media Concern: “You’re like, do you wanna babysit my kid? At a certain point, you start to go, are you really, really [concerned]?” – Dana, 11:26
• Hollywood’s Unspoken Rules: The tension between rooting for a friend and feeling overshadowed as careers diverge.

Important Timestamps

• 06:01: Emilio Estevez cameo
• 09:13: Reframing Tiger Blood era as comedy
• 13:49: “Winning” and “warlock” catchphrases origins (Brian Wilson story)
• 24:32: The “10/90 deal” and betting on yourself
• 28:09: Trying to exit Two and a Half Men
• 33:03: Sheen’s childhood & home movies
• 39:47: Not getting Karate Kid because of Grizzly
• 41:01: On being starstruck by acting with legends
• 43:38: Borrowing from Leslie Nielsen & Ted Danson
• 49:16: Letting go of collectibles
• 55:19: First impressions of Tom Cruise
• 64:02: Fight night bonding over “crush zone”

Overall Tone & Style

The tone is classic Spade/Carvey: breezy, self-deprecating, smart, and loaded with in-jokes. Charlie matches the hosts with candor, humility, and surprise vulnerability alongside his signature wit. The episode walks the line between nostalgia, legend-making, and a surprisingly nuanced look at fame, success, and the comedy in having—and sometimes losing—it all.

For the Listener:

This is a quintessential “Fly on the Wall” episode: hilarious, insider, revealing, and unexpectedly poignant—a treat for fans of comedy, Hollywood, or Charlie Sheen’s wild ride.

“I’d like to believe that I get invited back, that’d be amazing.”
– Charlie Sheen, 63:09