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I need right now with my biz plan. Get our best price as low as $25 a line. Visit verizon.combusiness to get started today. New lines only. Price per month with five plus lines includes auto pay and paper free billing and promotional discounts. Taxes, fees, economic adjustment charge applicable. Add ons prices and terms apply. Guarantee applies to base monthly rate and stated discounts only. Add on prices. Additional offers in March 31, 2026. Hello and welcome to this episode of Kennedy Saves the World. Joining me now for happy hour is my favorite almost Oscar winner, Kevin O'. Leary. Mr. Wonderful.
A
Yeah, you're right. Almost. You know, nine nominations, we didn't win anything.
B
I don't. Okay, so I have a theory about that, but I want to know your feelings.
A
You know, I think the way that everybody has a theory about it, but what I've learned is you will never know because 80% of the people I went to the Academy Awards and I realized 80% of the people nominated lose, right?
B
I mean, mathematically, yes.
A
Yes. And they're all losers. And it's very depressing because at the end of the thing when you're going to the governor's ball, the winners are holding their Oscars and. And the rest of us are losers
B
and then you go and you're not used to that.
A
No. And so I promised my team when I walked out, I'll fund the litigation. I mean, maybe we sue to get it back. I don't know. It was just an idea.
B
Have the social media lawsuits inspired you that maybe that's a different avenue you can take for recourse?
A
I think it would really piss the academy off. So probably not a good idea. But. But I did meet. It was a really interesting experience for me because I'd never done. I've done red carpets, but I've never done the Oscar. Red carpet.
B
Yes, that is the big one. It is unequaled.
A
But I must tell you something that I didn't realize. There's different levels of, let's call it, support. Let me give you an idea. If you're going to walk a red carpet somewhere, generally people want you to wear their brand of clothing or something or jewelry for the Oscars. Every brand on earth wants to work with you, okay, you get to go all around the world and basically say, I want to wear this, I want to wear that. The only problem with it didn't really work with my model was they wanted to lend it to me. So I'm like, rent the Runway or something.
B
Yeah, yeah.
A
And I said, everything I'm going to wear, I have to own. And Dolce said, we can't do that because these are museum pieces. One of a kind. I mean, they're in our museum. I said, well, they're going to go to my museum after this. If you want me to do this deal, let's negotiate a price. Same with the watches. I worked with Rolex on the left and Cartier on the right. Look at this piece from Rolex. Grown men are weeping looking at this because it married what I was putting around my neck, which is The Tiffany card, $30 million, very famous basketball card. But I thought to myself, it's such a competitive place, the red carpet. How am I going to break out? Why am I going to have a chance to do anything? So I came in swinging, and I had a hell of a good time.
B
Good for you. What were you most proud of that you wore?
A
Well, I was most proud when my stepfather, watching it in Switzerland, texted me and said, you look like a Greek Orthodox priest.
B
Oh, as. As an Eastern Orthodox Christian who is Chrismated and confirmed in the Greek Orthodox Church. That warms my heart.
A
Yeah, he was sort of insulting it.
B
I understand that, but. But I internalize that as the highest compliment. I think that's fantastic.
A
You said, why do you have to be so.
B
And it sounds like you're blessed.
A
Well, you know, he was. The family was critical of my accoutrement, my look that night. I got lots of compliments and a lot of people on me.
B
Yeah.
A
Who.
B
Who complimented you? Which A listers complimented you in the moment?
A
Well, my favorite moment was when I got to go to the green room because the Oscars prime sponsor now is Rolex and they have a green room. And I'm a huge Rolex collector. I was very fortunate.
B
Did you know the people from Rolex in the green room?
A
I did. Yeah, I did. And I also met the executives from Geneva headquarters. But they know me. I mean, I've been collecting Rolex my whole life. It was a great experience. But a couple of the A listers came up to me and said, you know, you didn't the bed in that movie.
B
Yes.
A
Which was a huge compliment for me because these were professionals and I'm just this guy, you Know that tried this, and it gave me a lot of confidence to look at the new scripts.
B
Devin, who works on our team, who watches things with a very critical eye, watched Marty supreme over the weekend before the Oscars and said that you were the best part. And she's not just saying that. Like, she doesn't have to tell me that. She could have pulled me aside and been like, Kevin o' Leary kind of sucked and ruined the movie. Like, she could have done that. We would have been fine. I never would have told you that. But she said he was the best part.
A
Well, it's very kind, but it's given me the courage to go now and start reading scripts.
B
I was gonna say, do you want to act more?
A
Yes. But I've realized something. There are a lot of bad scripts.
B
That's the hardest move an actor can make, is finding the role of a lifetime. Getting accolades, getting nominated, possibly winning, and then after that, having to line up the next wave of projects, because that's when they can really blow it. Because they're so worried that they're gonna miss out on something that they say yes to everything, and oftentimes half of it is garbage.
A
Yeah, I need to have the same experience I had on Marty Supreme. When I read the script, it blew me away. And so far, what I've seen, I can't. I asked the agents who's gonna fund this. This is terrible.
B
I'm sure a lot of people want to give you script, so you fund it.
A
Yeah, but I'm not a starving artist. I mean, I'm not. This is not what I do full time. So if I'm doing another one, it's got to be as good as Marty. I don't know how I can get better than what I had. I had a lister chalamet and, you know, Gwyneth Paltrow and Josh.
B
Did you hang out with all of them?
A
I did. We got to know each other, and we kept running into each other over and over again at all these parties because we promoted that movie for four months. So New York, L.A. you know, all over the world. We were in Tokyo, and we were shooting it. It was interesting, but I'd already met Paltrow. Gwyneth was on Shark Tank five years ago, Four years ago. So I already knew her. And I remember the first day we shot, we ran into each other and, oh, you know, it was like, you know, because we'd never rehearsed.
B
Is she down to earth?
A
Yeah, she's pretty normal.
B
What did you think of her dress? You could See a lot of her ass. And she got a lot of heat for that.
A
Yeah, yeah. She has a pretty. Pretty open attitude. She doesn't need, you know, body coaches and all that crap. When she shoots her love scenes, she's actually very professional. And, you know, she's also got a family, so she wants to work, wants to get it done, get finished, you know, doesn't want to work past 2 in the morning. That's my first time, so I worked all night. When we were shooting, it was. There's a lot of, you know, there's a lot of adrenaline. Then all of a sudden you're on your 50th take and you're just, oh, my goodness. You know. And that's where the best stuff happens. On the riffing of the improv stuff. Chalamet got a bad rap on this whole thing. I like that guy. He's very normal, and his mother is very nice.
B
Do you want to hear my theory?
A
Please.
B
He embodies the American dream. He's handsome, he's having a great time. He works his ass off. His work speaks for itself. And he's dating a Kardashian Jenner, and she is a beautiful Jessica Rabbit who's a billionaire in her own right. And he's with her not because he needs anything from her, but because he's a successful kid who's having a great time, and that's exactly what you should be doing. And I think all of these people are so incredibly jealous, not just of his talents, but the fact that he's not some mopey actor, you know, who's sitting around holding himself away from the world, that. That he's out there smiling, going to Timothee Chalamet lookalike contests, and he is the very best of America, and that drives them crazy. And then when he said what he said about the ballet and opera, which it wasn't a diss, he was just reciting data points, but, you know, somehow he's punished for that because he had the audacity to tell the truth. And all of these snobs are up in arms. When is the last time they went to the ballet or the opera? And could they even name one?
A
That is a very good observation. I'm going to add to it a little bit from the insider point of view. I don't know if you watch what happened to all of these operas and ballet troupes all around the world. They got such a lift of exposure, such an incredible amount of focus for almost four days, which is a long cycle before Something goes viral and they started using his name. You know, buy tickets with a 10% discount, special code, Timothy. I mean, that kind of thing. I would add one other element to what you talked about with the Kardashian, you know, thing. Kris Kardashian, I've got to know. Over the years, in hanging out in LA, shooting Shark Tank for almost 20 years, she provides a very comforting, I'm going to call it cocoon for her family. She understands the insanity of what they've created, but also understands family. And so if I were Chalamet and I understand, you know, it must be very easy for him to shove aside. I mean, this guy's like the Beatles. When we took a break and walked outside in New York in Times Square, I mean, it was like the Beatles in 1966. The police had to tape off all the girls.
B
My daughter had a Chalamet tracker app for a while.
A
So I said, timmy, all this, this is about me. But the point is when he goes to la, cause he's got his mother in New York who's a fantastic woman, really like her. But when he's in la, he's part of that Kardashian family, which I think would be very comforting. And I can see why he would do that. And he probably, you know, they're probably very happy together. So everybody should just leave him alone.
B
Yes, exactly. And stop questioning and stop projecting. He said that he didn't want to do a second take where you beat him in the bottom with a ping pong paddle.
A
Yeah, we had a stunt ass. It was 3:45 in the morning, and we had a fake paddle that had a silicon hinge. So when you whacked it, it didn't really hurt you. It broke on the first whack. But Timmy didn't want the stunt ass. He said, I'll do it myself because I'm going to immortalize my ass if this is going to happen.
B
It's absolutely right.
A
Plus, he didn't know what's he going to do, Inspect the stunt ass, make sure it's his ass comparable. Yeah, very risky, right? So he took the hits and Josh kept saying, it sounds fake, it looks fake. Because it did wind up and hit him, you know. So towards the end, I was alternating cheeks so that we could reduce the redness for the next take. Cause, you know, his ass was starting to radiate heat.
B
Is it underlined like, what is his ass like? Is it, Is it?
A
He's got a good ass. It's a good ass on me. And it's on the movie and you know, it's. But that last hit where his face explodes, I swear I hit him with a baseball bat like crazy.
B
But it was life changing for you, which I think is interesting because it had to have played to something more than your ego. Like there's something, it feels like there's something satisfying about that experience that you didn't expect. What was that?
A
Well, number one, my own agent, Josh Surrez or Jay Suras, who's one of the partners at uta. Yeah, you, you know, he's a major dude.
B
He's also UCLA Bruin.
A
Yeah, I, I like him just to note every watch he has I got for him. So just let's put that on the record. But the, he's, I've been working with him a long time. He's a great guy. He told me, you shouldn't do this, you're going to the bed. I said, what are you talking about? He said, hey, we have a great business with you. Look at what we've built together. Why would you want to take a risk like this? You're not an actor, you're going to suck. I said, how the do you, what, like what kind of support is this? He said, look, I'm just telling you what some of the guys here at the shop are thinking and maybe you should reconsider this. I said, well, that I'm doing it, you've motivated me to do it, I gotta try it. And I think the outcome has been good because it's now his agency that's showing me the new scripts.
B
That's absolutely right.
A
Yes. And I think, and I'm just telling the truth, he would agree. He, but he came to the movie on the premiere in LA and he said, not bad.
B
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B
So if you were playing someone less like yourself, are you prepared for that level of commitment in acting?
A
Well, you probably playing a homeless woman. Can you. Yeah, no, I, I can, I, I, I just, what I realized is it's not about typecasting. It doesn't Work if the script isn't great, Yeah, I don't care. I could be a divorced man. I could be anybody. But if the story sucks, you're going to fail. And I. I've just figured this out after all these years because I've only done it once and I've been looking at other stuff and wow, there's a lot of there. Yeah, I mean, it's a poopatorium.
B
Have you, have you produced movies in the past?
A
I have. I've been an investor with one of the founding shareholders of a company called mrc, Modi Zawicki. And Steve Satch, who started it, was one of the early investors. And Seven Years in Tibet was one of the projects I invested in. Remember all these things, but those guys changed the model.
B
Paul Pitt was a Nazi.
A
Well, it was like being like watching a movie for seven years. But my point is, they figured out how to change the risk model where you sold all the rights to every country except the U.S. they were one of the first to do that. And we did quite well financially on it. But I realized the risk is, you
B
know, Vinda Bona created that model for American television because he. He created America's Funniest Home Videos, which became America's Funniest Videos and sold it to every country. And that became the model for other people. I didn't even think that we could go over to Holland and do the same thing.
A
It was beautiful. That was a great show because it was so simple and pure and authentic and transparent and real, you know, I mean, it was great. I mean, you know, television format. I learned so much from Mark Burnett, the first guy to sit me down 20 years ago and say, hey, look, I'm looking for a real ass. This new show I'm doing, and you're it. It's called Shark Tank.
B
I love that everyone is so honest with you.
A
I know.
B
And I said, hey, listen, no one is deferential. Everyone wants to start a fight with you.
A
It's amazing. And then 20 years later, I hear the same words out of Josh Safdie on the dock of my cottage. I said, I've heard this movie before. He said, yeah, yeah, yeah, yeah. Listen, this is what we need, okay? This guy, you know, we think he's you because we're not doing the regular casting on this deal. You're going to read these lines. If we like it, you're it. I said, okay, let's do it. And then I changed the lines a bit because I said, if I was really in 1952, richest man in America, I wouldn't say that. I'd say this. So they rescripted it, which showed me a lot of support. And of course, by the time I started shooting it, I knew the story and I'd written some of the lines myself, so it wasn't that hard to get into it. But he's a great director. I mean, he really, really is a great director because he pulled stuff out of people. I was there, I was watching him do it. I mean, you know, he was good. Yeah, he's a. He's. He will win an Oscar one day because his stuff is good.
B
Yes.
A
You know, that movie's good. Well, Timothy, he should have won that. I'll tell you what I really feel, because I was at the awards, we should have won two out of the nine. The casting, the woman who did the casting, she should have won because nobody had a better cast than Marty Supreme. Such an eclectic cast. And Chalamet should have won best actor. That was a phenomenal performance. And you know, I'm biased because I was across from him when we were shooting it, but I mean, that sucked. You know, I'm not gonna say it's great. Everybody should. I'm pissed.
B
Yeah.
A
You know, good.
B
I mean, it seems like when you internalize anger, great things happen eventually.
A
No, I'm just telling the truth. For those two awards, I'm pissed. And you know, I'm being. I'm talking my own book. I would have liked to have said my first acting performance was in a Oscar winning movie. I'm proud to say it had nine nominations. But listen, I'm pissed. Those two should be.
B
Well, yeah, you can look at the other films and you, you know, I
A
did look at the other films. Not to. Not to shit on them, but I know what Marty supreme was better at.
B
Yes.
A
Because I'm pragmatic in that respect. Definitely casting. It was fantastic. All those characters.
B
Do you text with Kylie?
A
No. No, I don't. I met her. We met. You know, she.
B
I mean, can she hold a conversation?
A
Yes. Yes. You know, the funny thing is, I think she gets it must be hard to live in a bubble like that. You know, she's normal. I mean, it's not. They're all people. I mean, they're just not. When you're sitting around in the green room before you're going out to whatever the premiere is. We're all just normal people.
B
Yes.
A
We're talking about other stuff. I mean, Timmy's hot on watches, so we're comparing stuff. And the creator, he's a Watch guy. So we'd be. Anyways, it was just like. They're all just normal people and after 10 minutes, that's what they are.
B
Are they boring after 10 minutes?
A
No, no. It's just there you are, you're sitting in a room and you're just talking about stuff because what else are you going to do? Don't want to talk about the movie anymore. You've been doing it for nine months.
B
Does Leonardo DiCaprio just want to talk about the environment? I interviewed him when he was 16.
A
Yeah. I think, you know, I just saw him in the. They're, they're, they're all there in the green room. They come in and out during the. Remember, it's a four hour performance. Yeah. You can't sit for more than an hour and a half before you got to go up and take a pee. Pee. Let's. Let's think. And then some.
B
Not Gwyneth. Gwyneth was sewn into her dress.
A
Yeah.
B
I worry she was dehydrated.
A
Yeah. I mean, they have these runners that come sit in your seat.
B
Yeah. Seat fillers. Hard to get that job.
A
Well, mine was pretty good because he clapped good. I got to know him. I said, hey, you know, he was a nice guy. I said, what did they pay you for this? He said, oh, it's okay, you know, I just want to watch the Oscars.
B
Yes, of course.
A
Well, you are going to because we're going to be here for 4 hours and 10 minutes and then it's the parties start and you have to go. The thing, here's the thing, you gotta realize. And I'm not trying to. I mean, when I rate the experience of what that evening was like as the first newcomer kind of guy.
B
Yeah.
A
The most fun is the red carpet.
B
Yes.
A
Everything goes down.
B
I love red carpets because people. I don't realize that everyone is watching and paying attention and they say wild things and they're adjusting themselves and they have other people come up and fluff their gowns and hair and makeup people and teams of people just to make sure. Because those pictures live forever, whether you're in something hideous or something monumental. And I just, I love watching the flurry.
A
It was fun to be part of it. And then after that, it's rinse and repeat because you're there for four hours. And I'll make another observation as sort of an investor guy.
B
Yes.
A
You know, I met a lot of executives in the academy while I was there. Very interesting perspective because as you know, they have now sold the rights to YouTube yes. And this makes a lot of sense. There's no brand bigger on earth than the Oscars and it's under monetized in a huge way. Okay. Because if I were a corporation, I'm just now speculating, but I bet I'm going to be right. And you called me up and said, I have a box with 20 seats just like the F1. Because I do that at the F1 all the time. Would you like to bring your top clients for an evening at the Oscars? The price is 1.5 million. My answer would be yes, of course. As long as my people get treated properly, they get a great meal, maybe they get a tour backstage or something. I mean, that's what I would do with that brand. And when I see a brand like Rolex step up and become the prime, you know, sponsor, I'm thinking These guys have 200 year visions, but they know YouTube's gonna go global in multiple countries and that's where the Oscars are going, in my opinion. I don't know what the Academy's thinking, but I don't know how much money they make or lose. I don't look at the income statement, but when I see an opportunity like that, I would love to be part of that deal because that thing is going to be. I don't know anybody on earth and I travel the globe that doesn't know what the Oscars are.
B
Yes. And the brand needs some rehabilitation.
A
You don't say.
B
Yeah. So hopefully now with Mr. Wonderful's involvement, it will, it will be once again in a new prime. Which did you like better, the Governor's Ball or the Vanity Fair party?
A
I never made it to Vanity Fair because that was going to be the fourth party and I had to leave for Boston at 5am, wheels up at 6. So I thought I need four hours at least. But I was gonna get to the party thing. The party. Red carpets are cool, but inside they're all the same.
B
Okay.
A
Like you already saw that person at the last party. Like you're cruising around everywhere to all the parties and, oh, I just saw you 15 minutes ago at that party. And now we're at this party and we're at that party.
B
Now we have to have another awkward goodbye.
A
Yeah, I mean, it's sort of. You're gonna see slightly different people everywhere, but at some point you burn out.
B
Yes.
A
Like, it's just, you're, you've been. Remember this year, the security was unbelievable. There were dog sniffing things and bomb detectors and you had, you had a five minute slot for your number to be on the red carpet. And you were placed according to whatever. I mean, whoever organized that thing is a genius. I mean. I mean, I can't believe it worked out because the whole city was shut down down there. They had choppers in the sky.
B
Yeah. And then you also heard the FBI report that there was a plot for an Iranian missile or drone attack somewhere in California from sea. And it's like, okay, great. Is it here? Because there are so many notable people concentrated in one place. Does that make us a target? That has to be really scary for
A
anyone who's in town. No, no, but I would. I felt pretty comfortable going through the gauntlet.
B
Were you packing heat?
A
Well, in my case, yes, because I was walking in with that. Not me personally, but we hired guards, and we disclosed to the. There was a handoff of security on that necklace I was wearing. So we had security in the car. And then when I stepped on the red carpet, it shifted to the security that they had a lot of undercover guys.
B
It's like when you have a baby. You go from an obstetrician. All of a sudden, there's a pediatrician there.
A
Yeah, it felt like that. And then the red carpet, I felt very secure. Boy, they really managed that thing. And then we walked into the. That building's eclectic because it's full vertical. You're going up five levels of escalators, and the governor's ball is insane. I mean, wolfgang Puck feeds 1700 people in basically 45 minutes.
B
Wow.
A
It was. Anyways, it was a great experience. I'm glad I did it. And I think now I got to find a good script.
B
Well, here's to your future scripts.
A
Thank you so much.
B
All of your endeavors.
A
Yeah.
B
To Cheers.
A
Isn't it great to talk about something different than just oil prices?
B
Yes.
A
Cheers.
B
Now that we're hitting 120, how are you going to capitalize on the moment? This has been Kennedy Saves the World Happy hour along with Mr. Wonderful, Kevin O'. Leary. I'm Kennedy. Listen Ad free with a Fox News podcast plus subscription on Apple Podcast and Amazon Prime. Members can listen to this show at AD free on the Amazon music app. Oh, go ahead and leave me a review while you're there. I'd love to hear what you have to say. You've been listening to Kennedy Saves the World on the Fox News podcast network.
In this lively and candid "Happy Hour" episode, Kennedy chats with Kevin O’Leary, also known as “Mr. Wonderful,” about his whirlwind journey to the Oscars as a newly minted (almost) actor, his thoughts on Hollywood, rubbing elbows with A-listers, and the now-famous scene involving Timothée Chalamet. They banter about the surreal world of red carpets, the business of showbiz, and O’Leary’s surprise at finding himself in the thick of Oscar night traditions and drama—all delivered with Kennedy’s trademark wit and O’Leary’s hard-nosed pragmatism.
The episode is witty, irreverent, and packed with the sort of insider anecdotes and candid talk that Kennedy and Kevin O’Leary are known for. Kennedy’s tone is both playful and analytical, while Kevin’s responses alternate between tongue-in-cheek braggadocio and sincere awe at his whirlwind Hollywood experience—punctuated with frank business insight and a clear sense of fun.
For film buffs, Shark Tank fans, and anyone curious about a first-timer’s red carpet journey, this episode provides unforgettable moments, practical business wisdom, and a behind-the-scenes peek at the glamour and chaos of Oscar season.