Fly on the Wall with Dana Carvey and David Spade

Episode: Mr. Wonderful aka Kevin O’Leary: Shark Tank Meets Marty Supreme
Date: January 15, 2026

Episode Overview

In this lively episode, comedians Dana Carvey and David Spade welcome Kevin O'Leary—known to millions as "Mr. Wonderful" from Shark Tank—for an offbeat, insightful, and very funny conversation. The trio discusses O’Leary’s unexpected leap into acting with the Safdie brothers’ much-hyped movie Marty Supreme (co-starring Timothy Chalamet), the inner workings and evolution of Shark Tank, the realities of entrepreneurship, and O’Leary’s signature take-no-prisoners views on business, politics, and global economics. The episode is a wild ride blending showbiz banter, behind-the-scenes movie stories (highlighted by Chalamet's now infamous “ass double” anecdote), and hard-nosed financial wisdom—with plenty of irreverent humor throughout.

Key Discussion Points & Insights

1. Kevin O’Leary’s Leap into Acting

• Casting for a “Real Asshole” (01:34, 14:11)

  • O’Leary was approached by the Safdie brothers to play a villain in Marty Supreme:

    "They came to see me and said, look, we're looking for a real asshole in this and you're it." – Kevin O’Leary [01:34, 14:11]

  • He jokes about his character's evilness and disputes over the film’s ending:

    "I was very unhappy with the ending... if he really did this to me in real life, I would fuck him over so badly... I suggested to them, perhaps I'm a vampire and I bite him and he lives in hell in perpetuity." – Kevin O’Leary [14:33, 15:02]

• Working with the Safdies and Timothy Chalamet (13:22–18:41, 32:22)

  • Describes first-time acting and chemistry with Chalamet, including filming an intense paddle scene typically reserved for a double:

    "Timmy said, no, I want to immortalize my own ass in perpetuity. So I said, I have to hit your ass, it's going to hurt. So he rotated cheeks so they were equally red through 20 takes... I admire him for saying, look, I'm not letting a stunt ass immortalize my ass in perpetuity in a film." – Kevin O’Leary [17:31, 18:40, 32:22]

• Red Carpet & Industry Surrealism (31:05–33:47)

  • O’Leary, unused to Hollywood accolades, prepares for the NY premiere:

    "I've never done this kind of gig before, but boy, it's crazy... I love it when people suck up to me. I really do." – Kevin O’Leary [31:12, 31:47]

2. Shark Tank: Origin, Evolution & Impact

• From Audition to Family-Sized Hit (04:10, 07:04–09:20)

  • The show was canceled multiple times but survived due to becoming family-friendly TV:

    "It got canceled three years in a row... In the fourth year, it just went geometric." – Kevin O’Leary [07:10, 07:45] "It's the essence of the American dream... you can come up with a product... become a multimillionaire, which we've done countless times in 17 years." – Kevin O’Leary [08:31]

• Key to Entrepreneurial Success (09:33–13:05)

  • O'Leary explains business growth stages and why many founders stumble at scale:

    "The first million is easy... But getting, like, when you hit 5 million, you gotta start hiring people... A lot of people shit the bed when that happens." – Kevin O’Leary [09:33] "Big is 50 million... Most people that founded the company don't have [executional] skills and they go to zero because of it." – Kevin O’Leary [12:36]

• Notable Deals: Cat DNA Test Example (10:23, 11:56)

  • O’Leary highlights unlikely Shark Tank success stories:

    "Cat DNA tests... I can buy a new cat for five bucks, why spend $29 on a test? But... we made a lot of money, a ton. It was bought by a giant pharmaceutical company later for the data." – Kevin O’Leary [10:23, 11:56]

3. Business, Wealth, & Social Persona

• Philosophy on Wealth and Self-Confidence (04:10, 05:00)

  • O'Leary shrugs off billionaire comparisons:

    "I don't need any more money. I just need more time. That's my real issue." – Kevin O’Leary [04:10] "I look fabulous all the time. I can't believe how good I look." – Kevin O’Leary [04:45, 33:34]

• Truth-Telling and Dealing With Hate (05:21–06:22)

  • On embracing his controversial reputation:

    "My mother told me when I was 16: just tell the truth, you never have to remember what you said... I care about my family and maybe 15 friends and everybody else. I don't give a shit." – Kevin O’Leary [05:21]

• Shark Tank Dynamics & Relationship with Mark Cuban (22:29–24:51)

  • O’Leary and Cuban collaborate on deals—differing only on investment styles:

    "He likes equity, I like royalties... He's a little bit country, I'm a little bit rock and roll." – Kevin O’Leary [24:34]

4. Economics, Policy, and the American Dream

• Political Neutrality & The Policy Lens (26:34–27:21)

  • On navigating divisive times:

    "I'm a policy guy... I do as many hours on CNN as I do on Fox... I care: is this good policy? And that seems to have kept me out of trouble." – Kevin O’Leary [26:34]

• On America's “Secret Sauce” (27:21–29:09)

  • O’Leary as ambassador for the American Dream:

    "The number one export of America is not energy or technology. It's the American dream." – Kevin O’Leary [27:21] "Entrepreneurship's not money or greed. It's about pursuit of personal freedom to do whatever you want with your time." – Kevin O’Leary [28:45]

• Views on High-Tax States and Mobility (29:09–30:58, 35:02–36:34)

  • Wry comments on NY/CA taxes; the flight to Florida:

    "California... you guys are paying 99% tax." – Kevin O’Leary [29:09] "Everybody lives in Florida now. All my Boston neighbors... they live in Florida and they visit New York. I don't know who's going to pay the taxes here, but this isn't going to work." – Kevin O’Leary [30:37]

5. Global Economics, China, and North America’s Future

• Canada-US Economic Alliance & China Skepticism (35:02–36:34, 43:43–45:48)

  • O’Leary advocates for closer economic ties to counter China:

    "Canada has all the raw resources and the US is the largest market... and then tell the Chinese to fuck off." – Kevin O’Leary [35:03] "China is subsidizing EVs, selling it to every country at half what it really costs... We’re in economic war with those guys." – Kevin O’Leary [42:14, 44:04]

• IP Theft and Trade Realpolitik (44:04–45:11)

  • Frustration with Chinese business practices:

    "They steal everything. They have no IP laws, you can't sue them... I'm just telling the truth." – Kevin O’Leary [44:04]

6. Rapid-Fire: Crypto, CEOs, and Music

• Crypto for Beginners (37:02–39:46)

  • O'Leary's practical advice:

    "All you need to own in crypto... is Bitcoin and Ethereum. There are 10,000 shit coins. You don't need to own any of those." – Kevin O’Leary [37:13] "Don't own more than 5% of your portfolio in it. You can make about 3% yield on it, which is not a lot. Don't speculate too much." – Kevin O’Leary [38:00]

• On Elon Musk (40:13–41:58)

  • Why Musk stands apart as a CEO:

    "This guy is 100% signal, no noise. A little awkward socially... but he's only a third of the way through his career and look what he's achieved." – Kevin O’Leary [40:13]

• Music and Guitars (46:30–47:47)

  • O’Leary’s passion for guitars and his custom models:

    "I made a guitar with [Gibson]... a 355 George Harrison Red with a 335 neck. If you're into guitars that's a pretty cool guitar." – Kevin O’Leary [46:38]

Notable Quotes & Memorable Moments

• On Celebrity & Self-Image:

  "I can't believe how good I look... It's ridiculous how good I look. I'm almost embarrassed how spectacular I look."
  — Kevin O’Leary [33:34]

• On Shark Tank’s Appeal:

  "The reason it works is that we don't know. You don't know what's going to walk through those doors. It's the essence of the American dream."
  — Kevin O’Leary [08:31]

• On the “Ass Double” Scene:

  "Timmy said, no, I want to immortalize my own ass in perpetuity... An ass is an ass and there's only one ass. Make it your ass, celebrate your ass and put it in this film for generations to come."
  — Kevin O’Leary [32:22]

• On Entrepreneurship:

  "It's not money or greed. It's about personal freedom to do whatever you want with your time."
  — Kevin O’Leary [28:45]

• On Political Divides:

  "The number one export of America is not energy or technology. It's the American dream."
  — Kevin O’Leary [27:21]

• On Dealing with Hate:

  "Most of us hate mail. And then there's about two and a half percent, which I call the lunatic fringe, which is just... completely fucking crazy. And what am I supposed to do about that? Nothing."
  — Kevin O’Leary [06:22]

Timestamps for Key Segments

| Segment | Timestamp | |-----------------------------------------------|-------------| | Shark Tank origins and family appeal | 07:04–09:20 | | O’Leary joins the Safdies' film | 13:22–16:38 | | Timothy Chalamet paddling scene | 17:31–18:41 | | Crypto advice & stablecoins | 37:13–39:21 | | Praise for Elon Musk and story | 40:13–41:58 | | Perspective on America, taxes, and rivalry | 27:21–30:58 | | US-Canada economic strategy and China | 35:03–36:34, 43:43–45:48 | | Red carpet preparation, tuxedo fashion | 31:05–33:47 |

Final Thoughts

This episode delivers a fast-paced, funny, and unexpectedly deep conversation that spotlights Kevin O’Leary’s larger-than-life persona, his quick wit, and blunt business wisdom. Are the Safdie brothers "disturbed individuals"? Is America still the best economic game in town? What should we really do about China? And, most importantly—should every actor immortalize their own ass on film?

Whether you're a Shark Tank fan, curious about the modern business landscape, or just in it for the showbiz gossip and laughs, this episode provides an entertaining and insightful look behind the scenes with "Mr. Wonderful" himself.