Kennedy Classic: Kevin O'Leary and Rob Schneider

Summary

Kennedy Saves the World — "Kennedy Classic: Kevin O'Leary and Rob Schneider"

Date: January 1, 2026
Host: Kennedy
Guests: Kevin O’Leary, Rob Schneider

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Episode Overview

This special "classic" episode brings together entrepreneur and “Shark Tank” star Kevin O’Leary and comedian-actor Rob Schneider for lively, wide-ranging conversations on branding, culture, Hollywood, and freedom of expression. In Kennedy’s signature witty and candid style, the episode probes the nature of personal reinvention, the pitfalls of modern celebrity, the shifting boundaries of artistic freedom, and the real and perceived consequences of “woke” culture on the creative arts. Both guests offer colorful and unfiltered takes from their respective fields, resulting in a blend of humor and sharp insight.

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Key Discussion Points and Insights

1. Branding, Authenticity, and the Meghan Markle Example

(00:40–05:29)

• Kennedy engages Kevin O’Leary with the question of Meghan Markle’s persistent branding challenges since departing royal life.
• Kevin O’Leary likens Meghan and Harry's exit from the royal family to a disastrous business move:

  “The lesson is never get off the boat...When they decided to leave the royal family...that was an incredibly stupid decision because her whole brand was associated with royalty.” — Kevin O’Leary (01:09)

• O’Leary underscores the idea that Markle underestimated the value—and complex responsibilities—of her royal platform, noting missed opportunities for reconciliation, especially before the Queen’s death:

  “She could have crawled back but didn’t. And then the Queen died...I think she’s having a very hard time engaging the world as a housewife because that’s effectively what she’s become. A famous one.” — Kevin O’Leary (02:09)

• He highlights the branding lesson: marketers and family-oriented brands hesitate to align with those whose messaging and actions aren’t perceived as authentic or values-driven:

  “If you’re not authentic and you’re not real, people smell that a mile away...They may not agree with me, but they know what I’m saying is my truth for sure.” — Kevin O’Leary (04:56)

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2. Judging Pageants and the Nuances of Regret

(06:00–07:19)

• Kennedy shares a personal story of regret from the Miss Teen USA Pageant, where her scoring decision inadvertently changed the outcome—highlighting the unpredictable ripple effects of small choices.
• Rob Schneider connects with his own pageant judging experience, noting how the behind-the-scenes politics (like Trump’s preference for Miss Texas) and personal stories can sway outcomes—often in stark contrast to public perception.

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3. Trump, Politics, and Hollywood Dynamics

(07:20–10:51)

• Schneider recounts an awkward interaction with Trump, reinforcing humor in high-level circles, and pivots to his view on why Trump remains politically significant:

  “God has his reasons for picking people, and God has reasons why he wants Donald Trump to be president. And I sincerely believe that.” — Rob Schneider (08:55)

• The conversation moves to perceptions of the political divide, with Schneider critiquing Democratic elites’ disconnect from “flyover states” and emphasizing Trump’s resonance with average Americans.
• He details how shifts in political leadership affect Hollywood perspectives, especially when economic downturns impact the stock market:

  “I haven't had agents from Hollywood and managers call me until the stock market took a dump...they called me a few days ago, say, ‘What's your boy doing?’” — Rob Schneider (09:31)

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4. China, Trade, and Economic Power

(10:51–12:00)

• Schneider analyzes U.S.-China economic relations, arguing that China is more dependent on the American market than vice versa:

  “No one is going to push back against China like the United States did...it is a false economy. It is falsely inflated.” — Rob Schneider (10:27)

• He predicts significant pain for China if trade conflicts intensify, drawing distinctions between free vs. government-controlled markets.

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5. Freedom of Expression and Hollywood Creativity

(12:17–16:47)

• Kennedy jokes with Schneider about his film “Deuce Bigalow,” exploring the origins of the “unlikely hero” trope and how comedic freedom shaped his career.
• Schneider laments modern Hollywood’s hesitance to produce edgy comedies:

  “Disney made Deuce Bigalow...They’ll never do that again, which is sad because you gotta have funny movies. The idea that if a few people are offended, that that has to stop us from watching or listening to what we want...” — Rob Schneider (13:16)

• He invokes John Cleese’s wisdom:

  “The most sensitive people should not be the ones deciding what everybody else gets to listen to and enjoy. It’s true. Let us decide.” — Rob Schneider (13:36)

• Both critique the “woke” direction in media, arguing that audience choice, not activist pressure, should dictate content. Schneider references the strategic timing of movie releases as telltale signs of studio lack of confidence:

  “If you release your movie in March, it’s because you know it’s a turd and you’re trying to sneak it out there when there’s not much else.” — Rob Schneider (14:14)

• Kennedy and Schneider discuss the limitations (and ethics) of studios restricting actor speech on social media, weighing commercial interests against free expression.

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6. The Cost of Speaking Out

(16:47–18:07+)

• Schneider and Kennedy reflect on the personal and professional risks of public political expression—citing Oprah Winfrey’s arc as a cautionary tale:

  “Once you put your neck out there...you’re not going to get a Coca-Cola commercial.” — Rob Schneider (17:52)

• They close on the unresolved tension between commercial realities and the need for honest, open discourse in public life.

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Notable Quotes & Memorable Moments

• Kevin O’Leary on branding:

  “If you’re not authentic and you’re not real, people smell that a mile away.” (04:56)

• Rob Schneider on Hollywood politics:

  “God has his reasons for picking people, and God has reasons why he wants Donald Trump to be president. And I sincerely believe that.” (08:55)

• Schneider on freedom of choice in art:

  “The most sensitive people should not be the ones deciding what everybody else gets to listen to and enjoy.” (13:36)

• On the state of modern Disney:

  “They’ll never do that again, which is sad because you gotta have funny movies.” (13:16) “If you release your movie in March, it’s because you know it’s a turd.” (14:14)

• On the personal cost of opinions in public:

  “Once you put your neck out there...you’re not going to get a Coca-Cola commercial.” (17:52)

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Timestamps for Important Segments

• 00:40 — Kevin O’Leary on Meghan Markle & branding
• 05:50 — Transition to Rob Schneider’s segment
• 06:00 — Kennedy’s Miss Teen USA regret story
• 07:20 — Schneider on judging pageants and Trump
• 08:09 — Schneider recounts Trump interaction
• 09:17 — Effects of the stock market on Hollywood attitudes
• 10:51 — Schneider’s analysis of US-China trade
• 12:00 — Shift to comedy, movies, and “Deuce Bigalow”
• 13:36 — Quoting John Cleese on censorship and free speech
• 14:14 — Disney movie release strategies & commentary on “woke”
• 16:47 — Discussion on the limits of activism and speech in Hollywood
• 17:52 — The cost of political speech in show business

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Tone and Style

The episode balances sharp business logic, caustic humor, and political candor—true to Kennedy’s "spit-out-your-coffee" approach. O’Leary brings a cool, analytical perspective, while Schneider’s tone oscillates between irreverent wit and impassioned critique. Both guests are unafraid to speak bluntly and challenge prevailing orthodoxy.

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For listeners seeking insightful, fast-paced takes on celebrity, branding, politics, and cultural shifts—with signature Kennedy irreverence—this episode delivers a lively summary of America’s ongoing debates on freedom of choice and expression.

Transcript

[A]

Foreign. Hello and welcome to this episode of.

[B]

Kennedy Saves the World.

[A]

Happy holidays. We're taking a look back at some of our favorite interviews from 2025. Follow this feed to get the full interviews and all episodes of Kennedy Saves the World. And make sure to subscribe to the Kennedy saves the world YouTube channel episodes available every weeknight at 6:30pm with bonus content posted throughout the week. Mr.

[B]

Wonderful is back as promised because Kevin, welcome back to Kennedy Saves the World.

[C]

Thank you so much.

[A]

Let me ask you this because every.

[B]

Time I talk to you, you tell me about something else that has been added to your brand catalog. So Meghan Markle is trying to do the same thing, but she's had a lot of missteps. Is that because she's mishandling her her brand? Or is it because the press is just so dead set against her?

[C]

She has an overhang that's extremely difficult to escape? You know, there's a really good line in Apocalypse now, the movie, which I've never forgotten. In terms of business, there's a scene where the guy gets out of the boat to get go get some fresh mangoes or something and gets attacked by a tiger. Chases him back to the boat. And the lesson is never get off the boat. And so when they decided to leave the royal family collectively, the two of them, that was an incredibly stupid decision because her whole brand was associated with royalty and what she had risen to from nothing to becoming effectively a Royal. Which.0001% of the population ever gets to do. And yet there's a cost. Obviously. You're part of a very complicated family with a complicated history and a responsibility to a nation. All of these things are put on your shoulders. But you rise to that occasion for the benefits they provide for you and your children in perpetuity. Somehow she didn't figure that out. And she had probably three different times. She could have crawled back but didn't. And then the Queen died, which took away another path because I've always felt she was the matriarch. She could have gone there quietly and got on her knees and begged for forgiveness while the queen was alive and maybe, maybe would have been allowed back in. I'm not sure that path exists today. And I think she's having a very hard time engaging the world as a housewife because that's effectively what she's become. A famous one.

[B]

Sure.

[C]

But 50% of the market, particularly the British themselves, disdain for the disrespect that she and her husband gave to the royal platform. See, that's My, that's why marketers or brands are saying, well, you know, does she really rep my brand properly? From a family values point of view, you want, you want a very encompassing message. And I think that's eluding her right now.

[A]

Yes.

[C]

Would that be a good analysis, do you think?

[B]

I think that's a great analysis. I mean, especially coming from someone who is probably the world's foremost expert on branding and capitalization and figuring out pathways, because she obviously was ambitious and attractive and, you know, there's something about her that Harry fell deeply in love with and picked her to be the one. And, you know, she, she could have been the Disney movie, but she should.

[C]

Have been the princess. She could have been the princess, but you have to take a lot of, when you're the princess and you have to realize you are not number one.

[B]

I think that was the difficulty not being number one. And also I think the work she was doing was probably kind of boring. And I think that's what happens when you, you know, there's probably a hazing process you go through when you enter the royal family, where you're doing events that are not entirely sexy and.

[C]

No. Cause if you're not number one, you're doing the discount event.

[A]

Yes.

[C]

And so, I mean, I think the problem is you're still part of the platform and it provides you with a lot of things. And your children, it provides you with security, which they're struggling with now. It's very, very expensive to monitor a home 24 7. I mean, you know, they've got lots of nut bars running around going after them. So I, I, I really think at the end of the day, they made a mistake and now they're starting to pay for it. And, and for brand. The thing about branding is, as you've pointed out multiple times, if, if you're not authentic and you're not real, people smell a mile away.

[B]

Yes.

[C]

And so even if I, I've always thought this, a lot of people don't like me because I'm very blunt, but I think they respect me for being that way. And so they may not agree with me, but they know what I'm saying is my truth for sure. And I'm not lying to anybody, anything. And if I, you know, I say, look, I only represent things like this tequila. I drink this tequila. This is mine. I made it for me. And everybody knows that, certainly with my wines as well. But you'll never see a beer from me because I don't drink beer. I'm not going to bull and Say, look, this is a great beer. I don't drink it.

[B]

I'm going to slap my name on it and hope for the best.

[C]

No, because I wouldn't drink it because my glucose would spike.

[B]

Yeah.

[A]

This is Ainsley Earhart. Thank you for joining me for the 52 episode podcast series, the Life of.

[C]

Jesus A listening experience that will provide hope, comfort and understanding of the greatest story ever told. Listen and follow [e-mail] or wherever you listen to podcasts.

[A]

You have to get Rob Schneider's book. It is his first book, which is an absolute shock because it is so entertaining, it is historical, it is political.

[D]

Thank you.

[A]

But above all else, it is very, very funny. Rob Schneider, obviously comic, SNL alum, movie star, and now political firebrand, taking the heat to the streets of California and beyond. Rob, welcome to Kennedy Saves the World.

[D]

Thank you. Nice to see you again.

[A]

I was a judge on the Miss Teen US Pageant.

[D]

Wow.

[A]

And I hesitated when I was giving one of the contestants a score on her final speech. And I was going to give her an 8.5. And I, I hesitated and I put in 8 and I. And it, it registered as 8.0. And she gave this, like, eloquent, beautiful speech. And if I hadn't done that, she would have won.

[D]

And.

[A]

And I was like screaming during the commercial break, they're about to crown the winner. I'm like, I gave her another half a point, like, please, someone help me. And they're like, it's too late. That's your fault. That's not on us.

[B]

That's.

[D]

And you still thinking about it all this time later, right?

[A]

Yes, because the girl's mother saw me at the airport the next day and came up to me and was like, how dare you?

[B]

Like, she has been the most outspoken.

[A]

Eloquent, and she was absolutely right. But, you know, a girl named Charlotte, who was an orphan, who had been through the foster care system her entire life, she ended up winning, which is a pretty great.

[D]

That is a great.

[A]

Later, she might have, she might have done some adult films or something of that ilk. So it's like the road wasn't always.

[D]

It is easy for her after.

[A]

I know, but I, I felt for you because you had a contestant come in and she was like, you. She was a brunette. She's like, I don't even want to be here. My friend's saying, pretty, I need to pay for my last year medical school. And all the judges are like, oh, my God, like, she's really going to help people She's a doctor. And then what happened?

[D]

We all voted. Well, Donald Trump had wanted Miss Texas to win, and she was beautiful. Miss Texas, you know, and this other girl's also beautiful. She just wasn't, you know, as blonde and blah, blah, blah. She was as far away from blonde, if you know what I'm saying, you can imagine. And we voted for her because she said she was close. She just needed a hundred thousand dollars to become a doctor. And it was like, well, you know, we should vote for her and we'll just, you know, I'm sorry. I'm sure he'll understand. He didn't understand. He wanted to win Miss Universe. That's how much he loves America. But we did that and, and I don't, I don't regret it. And I'm sure he understands.

[B]

No, but he, you, you said you.

[A]

Went up to him and you were like, oh, remember we were on the Tonight show together? He's like, no, I don't remember. And he was like, yeah, I told him, you joke.

[D]

That was my mistake. He didn't remember.

[A]

Tell me the joke. Tell me the joke. I love jokes. Jokes are funny.

[B]

Tell me the joke.

[D]

Tell me the joke. I love jokes. Know the joke.

[A]

And then you tell him the joke. And what did he say?

[D]

Well, Donald Trump looked at him, he said, I hate you. No. And he said to me that I love this. They said, no, seriously, I hate you now. I hate you. And I was like, ah, why don't I have to bring it up? You know, but, but, you know, he, he was, he's been very nice and he was very nice to me and he knows that I'm a supporter and I know he loves this country. And I feel like the Democrats screwed up because they could have gotten rid of, they could have gotten rid of, of him by now and they would have had, blah, blah, blah, but they didn't. And like, God works in mysterious ways, and God works with people that you would never, you know, you would. God has his reasons for picking people, and God has reasons why he wants Donald Trump to be president. And I sincerely believe that.

[A]

James Carville doesn't believe that. James Carville's like, he hates this country.

[B]

James Carville, he just, he wants to.

[A]

Take down the stock market and take the country down.

[D]

Well, I'll tell you what, the stock market is 70% owned by Democrats. So I feel pain at all for the Democrats. I don't. You guys have had it. You don't care about the flyover states. You really don't. Donald Trump Does. This is his one chance to gain parity with other nations. And no other president would, would push people into the pain category. And the people who have power in this country, I got to tell you, I haven't had agents from Hollywood and managers call me until the stock market took a dump. And then yesterday had a big, one of its biggest days in history and they didn't call me yesterday, but they called me a few days ago, say what's your boy doing? You know, and as if I have any access to the, you know.

[A]

Yeah. Oh, let me call right now. Oh my God. Like I'll text him, I'll take care of this whole thing. I'm going to tell him to put a 90 day pause on non China tariffs and we'll so be fine. Like your 401k is now amazing. Thank me later.

[D]

Exactly. Well, I will say though, it's going to be bumpy and if for everybody, wait till June, give it two months, give it a couple of months mid June because it's going to continue to be bumpy. But the difference is no one, no president and no one in Europe, no one in South America, of course, because they don't really have, you know, the economic power. Brazil is, you know, could be and will be and it's a great country. India is a great country. But no one is going to push back against China like the United States did. And China, I'm sorry, but China does not have the economic, doesn't come anywhere near the economic that we have in the United States. It is a false economy. It is falsely inflated. They are not part of the, of the marketplace and currency. They don't, they're not, you know, they, they don't abide by the same rules.

[A]

The United, they don't like freedom of speech.

[D]

Not only that, but let's, they don't like weakness. Let's go to their economy. They have 2% of our trade is from China, 500 billion. That's significant. And it could affect prices and it could affect, you know, detrimentally some part of the, of our economy. But the United states is a 50% of products in the United States. I'm sorry, products made in China go to the United States. So if, you know, if they want to, the Chinese can be very stubborn and they can be very proud and if they stick to this, they will cause a real pain and a real depression. Not recession, a depression. People in China will die if they don't settle this, if they don't come to the negotiating table. And that's the difference between the United States and a free, a free economy, a free market, as opposed to a, a government supported undemocratic market, and that's China. So that they're going to have to, you know, do some real, they're gonna have to do some, some real thinking, some real soul searching.

[A]

I, I, I, I don't know if they're going to do soul searching because it is a godlessness.

[D]

It is a godless nation.

[A]

Let me ask you this. Like they, obviously we are in the middle of a transformation. You have undergone a personal transformation. You are a good Catholic, a loving husband and father. But at one time were you a man? And was that the inspiration for Deuce Bigelow? Because not. There was not a lot of manhole representation.

[D]

First of all, I, I played a guy who wasn't a, a gigolo. I played a guy who cleaned fish tanks. That was my image of myself. I've never, I knew that I was never going to get like the beautiful, gorgeous girls that I had crushes on in high school. I said, I just, I need something more than just being, you know, me, I need to be like a comedian or some girl. At least girls will find me funny and maybe that would be my end.

[A]

And better a comic than a magician.

[D]

So I saw the movie. Yes, absolutely. I saw the movie American Gigolo with Richard Gere, a very handsome man. And I thought like, well, and these beautiful women, I said, these beautiful women, they don't need to hire a jiggle. They can go anywhere they want to have any guy they want. And I said, who are the women that really need maybe perhaps gigolos? And I thought, well, maybe it's somebody who has narcolepsy or somebody who's one leg. So it was just a simple joke.

[A]

Tourette's.

[D]

Tourette's syndrome. Amy Poehler was hilarious. So to me it was just a silly movie that Disney made. Disney made Deuce Bigelow, they made the hot chick. They'll never do that again, which is sad because you gotta have funny movies. And the idea that, you know, if a few people are offended or say they're offended, that that has to stop us from watching or listening to what we want. And, and my, my good, dear friend John Cleese from Monty Python and, you know, the Life of, the Life of Brian and also the brilliant movie Fish Called Wanda. He said the most sensitive people should not be the ones deciding what everybody else gets to listen to and enjoy. And it's true. Let us decide. So we have to go back to being Adults and watching what we want and then, and listening and not letting these small group of miscreants and, and.

[A]

You know, and Disney executives, because they're the ones who are forcing a very sanitized, very narrow agenda.

[D]

But it's not just narrow. It's not just sanitized. It's also woke. And they're also shoving it down our throat and thankfully.

[A]

But no one's, no one's taking.

[D]

Well, yes. Right. So, I mean, I think the capitalism in that way is going to reinforce the fact that you're not going to shove woke up garbage down our throats. And I think Disney, I mean, obviously Disney learned a very valuable lesson. First of all, they released a Snow White in March, which is the, you know, the biggest. That, that March is like, for movies that are turds. It is not a movie. You want to release a movie, you know, in the, in May when kids are starting. You want to get ahead of the summer or you want to release it July 4th or at Christmas time. When you release your movie in March, it's because, you know it's a turd and you're trying to sneak it out there when there's not much else. And you're also trying to bury it, just get it out of the way. So Disney was stuck in that position. So that's what they did. I mean, I worked at Disney. I know for a fact that you never release a blockbuster in March. You just don't. Nobody does it. It is a turd. And they knew it was a turd. And they knew that girl had ruined the movie. And unfortunately, you know, now, I mean, there has to be an awareness for movie stars to, like, say, hey, listen, you know, I'm sure in the contracts you can't say anything. I mean, I'm not gonna say the guy's name, but he's a very famous actor. He does comedies, he does dramas, but mostly comedies. One of the biggest comedy actors of the early, you know, 2000s, Jim Carrey. I'm not gonna say. No, I'm not gonna say, but it's not Jim Carrey. He was one of the biggest guys and some of the biggest comedies.

[A]

Steve Carell.

[D]

No, no, no, it wasn't Steve Carell, but I will tell you.

[A]

Ben Affleck, Ben Stiller.

[D]

No, no, no, none of those guys. But you're getting closer. But what happened was they told him on Apple, and this is last year, a year ago, he had a new series coming out. And they said, listen, you can't say anything on social media. You have to stay out of it. And he agreed to it. And while I think that's an invasion of free speech, but it also, you kind of understand it because you have Apple Studios that's spending a lot of money to do a TV series and they're saying, you know what, you know, so there's that fine line free speech. But also, this is a commercial art form and we don't feel like you, we don't want to risk that. So, I mean, I don't know the answer to that.

[A]

I can't blame, I can't blame Disney for that. I mean, that's a private.

[D]

This is Apple. But Disney, Disney's a private company.

[A]

Yeah, but unfortunately, the words that blowhard actors, you know, put out there as though their farts are rose scented and you. Every social media post is a thing of intellectual perfection. They're the ones like the press loves to go back and find those things.

[D]

You're going to be like, I mean, when you, I mean, Oprah said this years ago to a friend of mine, Chaz Edelstein, and he told me, said like, I don't like past the five alarm chili. I don't like the, you know, I don't like Oprah. I think she's a crazy liar now. And I think she used to be, you know, a very interesting, passionate, considerate person. And I think she's an abject liar. And I have zero respect for Oprah now because she knew it was a lie. To just lie to people and say, if you vote for Donald Trump, you'll never get a chance to vote again. That was humiliating and embarrassing and what a lie. And where's the apology for that outrageous lie for that outrageous, you know, he's gonna turn this into a dictatorship. And it really is stunning that she would say that lie. But she also realized this when she supported Obama years ago. Once you could put your neck out there. And like, once I put my neck out there, you know, you're not going to get a Coca Cola commercial. You're not going to get. And I would never do it anyway because that sugar is completely terrible for you. And we have a child.

[A]

I do love Coke Zero, though.

[D]

It tastes well, I mean, Diet Coke. I mean, the president loves it. And I, I don't, you know, I don't want to take away people's rights. You have your right to drink it. But I'm saying, though it will cost you to say your political opinions. And I do think you have to, we have to still figure it out.

[A]

Listen, ad free with a Fox News Podcast plus subscription on Apple Podcasts and Amazon Prime. Members can listen to this show ad free on the Amazon Music app.

[D]

It.