Best Podcast Episodes About Leonardo DiCaprio

Best Podcast Episodes About Leonardo DiCaprio

Everything podcasters are saying about Leonardo DiCaprio — curated from top podcasts

Updated: Apr 01, 2026 – 18 episodes
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Ridealong has curated the best and most interesting podcasts and clips about Leonardo DiCaprio.

Top Podcast Clips About Leonardo DiCaprio

The Flycast
“… even have done the interview. Yeah. But, like, there are people like that, like Eminem and Kendrick. But there's real people like that. Leo, Leonardo DiCaprio. There's people that you don't see them unless it's their art, so they seem mysterious. Right. But I wonder if these guys are just nerds. Kendrick is. For sure. For sure. Eminem is, I think, genuinely weird, a little off. Yeah. And he doesn't want to do that. He's not comfortable with that. Yeah. I think Kendrick's more like, if I do an interview, people are going to see how I'm not that cool. Now you're just hating. I was the nerd in Compton, …” “Kendrick would have tried to be mysterious. I don't know. Kendrick wouldn't even have done the interview. Yeah. But, like, there are people like that, like Eminem and Kendrick. But there's real people like that. Leo, Leonardo DiCaprio. There's people that you don't see them unless it's their art, so they seem mysterious. Right. But I wonder if these guys are just nerds. Kendrick is. For sure. For sure. Eminem is, I think, genuinely weird, a little off. Yeah. And he doesn't want to do that. He's not comfortable with that. Yeah. I think Kendrick's more like, if I do an interview, people are going to see how I'm not that cool. Now you're just hating. I was the nerd in Compton, and half the shit I write about ain't really facts. No, I'm just kidding. Now you're just hating. No, he's done some interviews before. Yeah, I watched the interview he did with Rick Rubin back in the day. It was like, in Compton? Yeah. That was fire. Yeah. But, like, there's, I don't know. It makes me think about it. even drake i'm like you should …” View more
Ridealong summary
Did you know Kendrick Lamar once played a homeless character in 'Power'? The discussion dives into how artists like Kendrick and Drake approach their public personas and acting aspirations. While Kendrick keeps a mysterious vibe, Drake's humor shines through, leading to a debate about their potential in acting.
The Flycast · The Only Person To Get Arrested in OpTic 😂 | The Flycast Ep. 184 · Apr 01, 2026
The Rewatchables
“… along the way. So it's really interesting in that way. He's a little bit, I don't even know if he's a little bit older, how much older than DiCaprio is he? Like maybe five, six years. Right. I, for him, it's not LA confidential. That's always the big question mark for me. It's memento because I think it would be relatively easy to project him into a number of Christopher Nolan leading roles going forward. And at which point you start to get into like, could that guy have been Batman? Like, well, there is like, there, there are a bunch of bail movies you could have thrown in and he probably …” “… cooking, like he's still doing his best work right now, says a lot. Crow is in a way different place. So the legacies are kind of perfect, right? Because one guy really went up, the other guy did fine. Yeah. And then they kind of traded places somewhere along the way. So it's really interesting in that way. He's a little bit, I don't even know if he's a little bit older, how much older than DiCaprio is he? Like maybe five, six years. Right. I, for him, it's not LA confidential. That's always the big question mark for me. It's memento because I think it would be relatively easy to project him into a number of Christopher Nolan leading roles going forward. And at which point you start to get into like, could that guy have been Batman? Like, well, there is like, there, there are a bunch of bail movies you could have thrown in and he probably would have been able to drive the car, but that's, that's it. We can save this for the casting part, but this was a question I had too, because obviously the casting makes this movie and the cast, was kind of not controversial, but more challenging because Curtis Hanson said he wanted unknowns so that the audience didn't have preconceived notions. …” View more
Ridealong summary
The casting choices in 'L.A. Confidential' led to fascinating career trajectories for its stars, particularly Guy Pearce and Russell Crowe. While Crowe achieved greater fame, Pearce's ongoing work showcases his versatility, raising the intriguing question of what could have been if casting had gone differently. The discussion touches on potential casting alternatives, including Matthew McConaughey, and how these decisions shaped the film's legacy.
The Rewatchables · ‘L.A. Confidential’ With Bill Simmons, Chris Ryan, Sean Fennessey, and Andy Greenwald · Mar 31, 2026
Adam Carolla Show
“… they're just selling out on the street that never existed. There is no enforcement at all because that is their constituency. see. I think I saw Leonardo DiCaprio selling a pinata the other day. Was that him? That was him.” “… afoul of them. So thus they don't enforce anything without. It's the same with all the street vendors. It looks like a bazaar in India. When you go to Los Angeles now, people are selling tacos and blankets and pinatas. I mean, all over every sidewalk, they're just selling out on the street that never existed. There is no enforcement at all because that is their constituency. see. I think I saw Leonardo DiCaprio selling a pinata the other day. Was that him? That was him.” View more
Ridealong summary
In this hilarious segment, Bill O'Reilly compares the absurdity of illegal leaf blowers to the bizarre sight of Leonardo DiCaprio selling pinatas on the streets of Los Angeles. The commentary on political correctness and enforcement—or lack thereof—of laws adds a comedic twist, making it both entertaining and thought-provoking.
Adam Carolla Show · Bill O’Reilly on Trump’s Next Move & Why America Is at a Turning Point · Mar 25, 2026
SmartLess
“… I was feeding. Yeah, and go deep like that. Yeah, that's really cool. I remember watching What's Eating Gilbert Grape and I'd never even heard of Leonardo DiCaprio. It's my sister's favorite movie. So good. And when Leonardo DiCaprio came on as that character, I was like, oh my gosh, how did they cast that kid?” “… kind of, it's a very specific experience that I don't know that I have to learn about. And I talked to kids that had it. And so that was very unique. And just to be, for the first time, like the person who was like number one on the call sheet, like I was feeding. Yeah, and go deep like that. Yeah, that's really cool. I remember watching What's Eating Gilbert Grape and I'd never even heard of Leonardo DiCaprio. It's my sister's favorite movie. So good. And when Leonardo DiCaprio came on as that character, I was like, oh my gosh, how did they cast that kid?” View more
Ridealong summary
In this hilarious segment, the guest shares their bizarre acting experiences, including being a demon child who burns down houses and getting kidnapped twice in the same role. The comedic banter about how quickly one would be let go after being kidnapped adds a layer of absurdity that makes this segment entertaining and relatable.
SmartLess · "Elle Fanning" · Mar 30, 2026
Andrew Schulz's Flagrant with Akaash Singh
“… why do you correct to 25 he's fucking like 45 first of all he's 50 if he was fucking 50 year old women I would shoot him in the head myself this is Leonardo DiCaprio wouldn't you shake the shit out of him if he was banging age appropriate who's 50 years old he can do like 30 what's this right here That's an infographic of Leo's age versus the girl's. So the limit is 25. But he goes in peaks and valleys. Oh, wow. This is a good use of an infographic. That is fucking hilarious. Okay, so are we really going to blame a guy who's 50 for wanting to bang 25-year-olds? When you jerk off to porn, you look for …” “… in entertainment you don't talk on podcasts so do you think it's worse for leo if he goes on a podcast than keeps fucking 22 year olds 25 25 that's his yeah come on dude nobody's really upset at him for that right like wouldn't you be more upset why do you correct to 25 he's fucking like 45 first of all he's 50 if he was fucking 50 year old women I would shoot him in the head myself this is Leonardo DiCaprio wouldn't you shake the shit out of him if he was banging age appropriate who's 50 years old he can do like 30 what's this right here That's an infographic of Leo's age versus the girl's. So the limit is 25. But he goes in peaks and valleys. Oh, wow. This is a good use of an infographic. That is fucking hilarious. Okay, so are we really going to blame a guy who's 50 for wanting to bang 25-year-olds? When you jerk off to porn, you look for age-appropriate women? Why do we got to do that? It's ridiculous, right? There's no category for it. Close my eyes and think about my wife. While she sitting next to you I just thinking about his weekends though think about her at 25 i don understand this like i mean that the thing we only know and nicky glazer had this fucking great joke i think it was …” View more
Ridealong summary
In this hilarious segment, the hosts debate Leonardo DiCaprio's penchant for dating 25-year-olds, humorously questioning if anyone would actually be upset if he dated women his age. The discussion is punctuated by witty observations and jokes, including the absurdity of a 50-year-old man being criticized for his dating choices while offering a comedic infographic to drive the point home.
Andrew Schulz's Flagrant with Akaash Singh · Shapiro’s Eyebrows, Chalamet Should Learn from Leo, & Are Jamaicans Irish? | #695 · Mar 11, 2026
The Big Picture
“… well might we just don't know but the other thing there is okay if they're not going for michael b jordan is the vote splitting between wagner mora leonardo dicaprio chalamet like that there's some harebrained thinking out there that chalamet who still has a lot of supporters yeah and and mbj would split and that that would be the pathway for a Wagner or for a Leo to climb up. I think that's, I almost did it, man. I almost, almost, I almost, I almost picked Leo. And I know I've been kind of wish casting that throughout the year. I would be elated if Leo won. I would feel for Michael B. Jordan as well, …” “… thinks of sinners and i i think this is to your point about having two acting wins and maybe more plus a screenplay win this is a movie that's going to have to play for the new academy in a way that i'm not sure if it will it might yeah it very well might we just don't know but the other thing there is okay if they're not going for michael b jordan is the vote splitting between wagner mora leonardo dicaprio chalamet like that there's some harebrained thinking out there that chalamet who still has a lot of supporters yeah and and mbj would split and that that would be the pathway for a Wagner or for a Leo to climb up. I think that's, I almost did it, man. I almost, almost, I almost, I almost picked Leo. And I know I've been kind of wish casting that throughout the year. I would be elated if Leo won. I would feel for Michael B. Jordan as well, because that, the thing you were talking about at the beginning of this, like this is about emotions. And Michael B. on stage at SAG felt so good. Yeah, I agree, I agree. And for all of the reason you just said, and I do think that that has weight. And so I do also think that if if Leo wins, I would feel sad because the Michael B. Jordan thing would …” View more
Ridealong summary
In the discussion about Oscar predictions, Michael B. Jordan's potential for a Best Actor win is put under the spotlight. Despite his popularity and heartfelt performances, questions arise about vote-splitting with other nominees like Leonardo DiCaprio and Timothée Chalamet, complicating his chances. The conversation also touches on the impact of recent comments made by Chalamet that stirred some controversy among Oscar voters.
The Big Picture · Our Final 2026 Oscar Predictions: Who Will Win, and Who Should Win · Mar 12, 2026
Handsome
“… of you, Tig, in the Oscar class photo of like all the nominees. And it just blew my mind. I saw it today on Entertainment Tonight. And it's like Leonardo DiCaprio, all these nominees. And there's our little handsome Tig right in the middle. Yep, yep, yep. Right in the middle. That was really fun. I mean, obviously, the whole process is exciting and fun. But it's such a nice thing. like today was the luncheon. What's the difference between lunch and a luncheon? Don't know. Maybe there's an Oscar somewhere. But so yeah, it was like press in the morning, then the lunch slash luncheon. And after you eat, …” “How's everyone doing? I'm doing well. I just re-shared a picture of you, Tig, in the Oscar class photo of like all the nominees. And it just blew my mind. I saw it today on Entertainment Tonight. And it's like Leonardo DiCaprio, all these nominees. And there's our little handsome Tig right in the middle. Yep, yep, yep. Right in the middle. That was really fun. I mean, obviously, the whole process is exciting and fun. But it's such a nice thing. like today was the luncheon. What's the difference between lunch and a luncheon? Don't know. Maybe there's an Oscar somewhere. But so yeah, it was like press in the morning, then the lunch slash luncheon. And after you eat, then they call each person up individually. And everyone cheers, but it was actually really nice and fun. And like, I just was standing up there going, God, I don't know. I know maybe five people up here personally, but I felt so proud of everybody. I was so overwhelmed with like, God, good job, everyone. You know, she's riled. Yes, yes. But yeah, it …” View more
Ridealong summary
In a hilarious moment, Tig shares his overwhelming pride at the Oscar luncheon, only to pivot to a comical discussion about Leonardo DiCaprio's vaping habits. The banter escalates as they joke about wanting to be Leo in various iconic roles, revealing their playful obsession with the star's charm and looks.
Handsome · Jane Fonda asks about hope · Mar 10, 2026
Adam Carolla Show
“… basically. Like I got a gun to me. I'm getting a boner. I want to have sex with a black chick. I will say this. They don't do this enough. But Leonardo DiCaprio's character, if that guy was an actual human being, he'd be the worst human being you've ever met in your life. Absolutely. Yes. Fucking shrunk out on weed, makes bombs, neglects his family, doesn't fucking work, hates the government. That's the worst human being on the planet. It didn't – the whole thing is run by some white supremacist cabal from someone's basement while they'll wear Hawaiian shirts and drive Mustangs. It was a shitty movie. …” “… and shit. Same shit we want. That's what they want. So the beginning of the movie is like, we're just going to go free some Mexicans. Which is super racist, by the way. Then they do that. Then everyone is like, Sean Penn's character is out of a cartoon, basically. Like I got a gun to me. I'm getting a boner. I want to have sex with a black chick. I will say this. They don't do this enough. But Leonardo DiCaprio's character, if that guy was an actual human being, he'd be the worst human being you've ever met in your life. Absolutely. Yes. Fucking shrunk out on weed, makes bombs, neglects his family, doesn't fucking work, hates the government. That's the worst human being on the planet. It didn't – the whole thing is run by some white supremacist cabal from someone's basement while they'll wear Hawaiian shirts and drive Mustangs. It was a shitty movie. It's not even a good movie. Shot well. Yeah. Interesting to watch. Bad story. Not even close. And by the way, these movies that are best picture, like, you know, the other in the past, when those types of movies come around, like Casino came on the other day. I just see Casino. I'm like, oh, I'm watching this. Like, you know, Casino or a Tarantino …” View more
Ridealong summary
In this segment, the host humorously critiques a movie where characters attempt to 'free' Mexicans but end up revealing their own absurdity. The comparison of Leonardo DiCaprio's character to the 'worst human being' and the outrageous depiction of a white supremacist cabal adds layers of comedy to the critique, making it both entertaining and thought-provoking.
Adam Carolla Show · Dan Abrams: Why People Hate Cops & What the Media Gets Wrong · Mar 17, 2026
The Big Picture
“… movies. And when a big star comes becomes involved in a movie, they have a lot of opinions. They have a lot of strong point of view about what is a Leonardo DiCaprio movie. And then they collaborate with the filmmaker and they make sure that the character that they're playing in the film at large kind of works with that persona. that it fits who they are. You know, if you look in the 90s, you see Will Smith doing this. You see Nicolas Cage doing this. Of course, Hanks and Cruz do this. They have a really, because of all of the power that they've accumulated, they get to collaborate more than your, you know, …” “… Nicholson would have. Exactly. Yeah, I mean, I love Leo. We've been saying for 10 years, Leo is he's the guy of the generation without question. I do think that he has a very similar thing to which you learn about the more you talk to people who make movies. And when a big star comes becomes involved in a movie, they have a lot of opinions. They have a lot of strong point of view about what is a Leonardo DiCaprio movie. And then they collaborate with the filmmaker and they make sure that the character that they're playing in the film at large kind of works with that persona. that it fits who they are. You know, if you look in the 90s, you see Will Smith doing this. You see Nicolas Cage doing this. Of course, Hanks and Cruz do this. They have a really, because of all of the power that they've accumulated, they get to collaborate more than your, you know, run of the mill movie star.” View more
Ridealong summary
Leonardo DiCaprio's star power is compared to legends like Marlon Brando and Jack Nicholson, highlighting his unique approach to Hollywood. The discussion reflects on how DiCaprio, much like past stars, shapes his roles and public persona, influencing the film industry. This segment dives into the evolution of movie stardom, examining DiCaprio's deliberate choices and impact on cinema today.
The Big Picture · The Oscar Hangover Mailbag. Plus: ‘Dune: Part Three’ Is Coming! · Mar 17, 2026
Blank Check with Griffin & David
“… I think it's partly because directors come to him being like, I want to make Inception. Exactly. And even I, Christopher Nolan, might need you, Leonardo DiCaprio, to actually get $200 million for my Dream Thief movie. You know what I mean? I can't explain this movie in an elevator pitch. Are you kidding? It takes me at least 10 minutes to explain the premise. The movie is an instruction manual. So Paris folds on itself. It sure does. um well i i mean i think the thing that is interesting to me about leo's recent choices are the like the ways in which those parts uh i mean like ernest burkhart and …” “… a movie actor. I mean, he also just, I mean, as someone who has liked a big paycheck. He usually will get your, he'll get a big paycheck. And that has affected the particular types of movies that he has made. Yeah, if it's like a $20 million or bust. I think it's partly because directors come to him being like, I want to make Inception. Exactly. And even I, Christopher Nolan, might need you, Leonardo DiCaprio, to actually get $200 million for my Dream Thief movie. You know what I mean? I can't explain this movie in an elevator pitch. Are you kidding? It takes me at least 10 minutes to explain the premise. The movie is an instruction manual. So Paris folds on itself. It sure does. um well i i mean i think the thing that is interesting to me about leo's recent choices are the like the ways in which those parts uh i mean like ernest burkhart and killers of the flower moon and particularly the narrative of killers you know where they were like he is not going to be the proto fbi agent right and that's like the movie is gonna be based around that like the initial envisioning you know we're going to reshape this movie to be driven by the indigenous characters. It's rude that they stumped him for …” View more
Ridealong summary
Leonardo DiCaprio's Oscar history reveals a complicated relationship with the Academy, marked by both recognition and resentment. Despite his early nominations for films like 'What's Eating Gilbert Grape,' DiCaprio's journey has been fraught with snubs, as the industry often viewed him as a pretty boy rather than a serious actor. This segment dives into his evolution from a teen idol to an acclaimed star, exploring how his past and the Academy's perception have shaped his Oscar journey.
Blank Check with Griffin & David · Critical Darlings: One Battle After Another And Oscar Predictions with David Sims · Mar 12, 2026
The Bobby Bones Show
“There's an article in Teen Beat 1991 where DiCaprio lists all his favorite stuff. So he's just a kid. So I'll tell you what he said and you tell me what yours is. First ambition, DiCaprio said acting. We'll do ours. What was yours? Veterinarian. I'm going to do, yeah, radio. Yeah, you always knew. You did it. All right. First album bought. His was Michael Jackson's Thriller. I mean, probably with my own money, Alanis Morissette, Jagged Pill. Yeah, Jagged Little Pill? Mm-hmm. I think mine was, I …” “There's an article in Teen Beat 1991 where DiCaprio lists all his favorite stuff. So he's just a kid. So I'll tell you what he said and you tell me what yours is. First ambition, DiCaprio said acting. We'll do ours. What was yours? Veterinarian. I'm going to do, yeah, radio. Yeah, you always knew. You did it. All right. First album bought. His was Michael Jackson's Thriller. I mean, probably with my own money, Alanis Morissette, Jagged Pill. Yeah, Jagged Little Pill? Mm-hmm. I think mine was, I bought two at the same time, ACDC Ball Breaker, and I bought Mariah Carey Butterflies. Quite the difference. Interesting. At the same time, yeah. Favorite book? As a kid? No, do it as an adult. You can't pick the Bible, because that's the one. Oh, that's a good one, though. I mean, I haven't had an obsession quite like the one I had when I was …” View more
Ridealong summary
The hosts hilariously compare their childhood favorites to a young DiCaprio's picks from a 1991 Teen Beat article. The absurdity of their contrasting choices, like DiCaprio's love for Harry Connick Jr. versus a host's pick of John Mayer, makes for a laugh-out-loud segment filled with nostalgic charm and playful banter.
The Bobby Bones Show · WEDS: When Amy Cried Before The Show + Medications We Take + Never Gonna Get It: We ALL Have 10,000 Of These! · Mar 18, 2026
The Bill Simmons Podcast
“… back and forth between chalamet and vagnar mora in the in the secret agent but those would have been my top two options and i you know i know that dicaprio you know i woke up like this i feel like he kind of can do these things in his sleep you know but he did a version of the same thing in killers of the flower moon and it was terrible right he was not good in that movie and he got such control over the material here in one battle after i also think he's better directed in one battle after another which is a wild thing to say about martin scorsese directing dicaprio because you know that …” “… know like i i would not have voted for him for best actor i just wouldn't have because i'm really not i'm so much less about my feelings when it would you vote for uh i would have gone wagner mora timothy chalamet although i would have probably gone back and forth between chalamet and vagnar mora in the in the secret agent but those would have been my top two options and i you know i know that dicaprio you know i woke up like this i feel like he kind of can do these things in his sleep you know but he did a version of the same thing in killers of the flower moon and it was terrible right he was not good in that movie and he got such control over the material here in one battle after i also think he's better directed in one battle after another which is a wild thing to say about martin scorsese directing dicaprio because you know that relationship right but i i just think that the comedy of this movie is what he could lean into and there's so that the comedy in one battle after another is so elastic that it just gives all the things that dicaprio is good at someplace to go like i think that that stretch from when he gets to um uh sergio san carlos's benicio del toro's um um karate …” View more
Ridealong summary
Leonardo DiCaprio's performance in 'One Battle After Another' showcases his talent for physical comedy, rivaling his iconic moments in 'Wolf of Wall Street.' While many might expect him to dominate awards, the speaker argues that other actors like Wagner Mora and Timothy Chalamet deserved more recognition. This perspective highlights the nuances of DiCaprio's acting and the importance of direction in his performances.
The Bill Simmons Podcast · LakerMania, NBA Expansion, WBC Lessons, and MBJ’s Moment With Billy Gil and Wesley Morris · Mar 20, 2026
The Viall Files
“… you think um do you think Tim upset Or do you feel like he like you think so Yeah I would imagine he is I do want him to have the same career that Leonardo DiCaprio has, where every time he's in a movie, he gets nominated, never wins. Then he's in a movie that everyone's like, this one's fine. And then he wins. Yeah. Yeah. That's kind of my, that's what I see for him. Little Timmy Tim Tim. I just love how winning the Oscar, we've really peeled back the curtains to how commercialized and performative this whole campaign is. And it seems to have almost nothing to do with the actual performances. Oh, yeah. It …” “… was going to be about vampires and i was or the blues i or the blues exactly it's like two awesome things vampires and the blues this is taking a turn okay so they fighting the net yeah okay and playing guitar and having sex like it a great movie do you think um do you think Tim upset Or do you feel like he like you think so Yeah I would imagine he is I do want him to have the same career that Leonardo DiCaprio has, where every time he's in a movie, he gets nominated, never wins. Then he's in a movie that everyone's like, this one's fine. And then he wins. Yeah. Yeah. That's kind of my, that's what I see for him. Little Timmy Tim Tim. I just love how winning the Oscar, we've really peeled back the curtains to how commercialized and performative this whole campaign is. And it seems to have almost nothing to do with the actual performances. Oh, yeah. It has so much to do with the... The fundraising on the side. The fundraising, the... Campaign. Kissing in the house. All the different events and networking. yeah it was interesting this year i noticed a lot in the speeches that amy matt like well amy madigan won for her role in weapons it's amazing she's amazing it was a win for the divas was amy …” View more
Ridealong summary
The recent Oscars highlighted how commercialized and performative the nomination campaigns can be, overshadowing actual performances. Notably, Amy Madigan's win for her role in a horror film sparked discussions about the community built among nominees during the campaign process. This year, speeches focused on relationships formed rather than just the honor of being nominated, revealing a deeper side to the awards.
The Viall Files · E1095 - Age of Attraction w/ Libby, Vanelle & Justin, Mormon Wives, The Oscars, RHOBH & Southern Hospitality · Mar 17, 2026
Connections Podcast
“… them both. The actor in a leading role nominees are Michael B. Jordan for Sinners, Wagner Mora for The Secret Agent, Ethan Hawke for Blue Moon, Leonardo DiCaprio, One Battle After Another, Timothy Chalamet for Marty Supreme here And Patrick wrote in to ask, is Leonardo DiCaprio great? I think he's asking, is he great in this movie? Generally. Is he in the greatness pantheon now, Scott? He's awesome in this movie. And I think he's been in enough good roles where he's up. When he's in a movie, you pay attention generally. You'll give him that. Okay, Cielo? Yeah. He's the best. Yeah? Is he good in this? …” “Director will be interesting between Paul Thomas Anderson and Ryan Coogler who directed Sinners. I think that is really where the interest of this ceremony is between those two movies, which are both great. I liked them both. The actor in a leading role nominees are Michael B. Jordan for Sinners, Wagner Mora for The Secret Agent, Ethan Hawke for Blue Moon, Leonardo DiCaprio, One Battle After Another, Timothy Chalamet for Marty Supreme here And Patrick wrote in to ask, is Leonardo DiCaprio great? I think he's asking, is he great in this movie? Generally. Is he in the greatness pantheon now, Scott? He's awesome in this movie. And I think he's been in enough good roles where he's up. When he's in a movie, you pay attention generally. You'll give him that. Okay, Cielo? Yeah. He's the best. Yeah? Is he good in this? What is he in here? One Battle After the End. Oh, One Battle After the End. Yeah, we all established that it's going to win and Scott's going to be wrong. probably so here probably is he great jared case is he a great actor i think at this point time yeah i mean when we talk about timothy chalamet is he a great actor now i don't see that i look at …” View more
Ridealong summary
Michael B. Jordan's performance in 'Sinners' is strong enough to overshadow Leonardo DiCaprio's role in a Best Picture contender.
Connections Podcast · Who will win — and who should win — at this year's Oscars? · Mar 04, 2026
The Bill Simmons Podcast
Ridealong summary
Despite being a long shot, Leonardo DiCaprio's chances of winning Best Actor are gaining traction due to his strong industry presence and the affection for his latest film. With a more international Academy and rising competition from actors like Michael B. Jordan, the race is more unpredictable than ever, making the stakes high for veterans and newcomers alike.
The Bill Simmons Podcast · NFL Over/Unders, an Oscars Preview, and a Brady-Pats Feud | With Cousin Sal, Sean Fennessey, and Seth Wickersham · Mar 11, 2026
The Big Picture
“… i mentioned um speaking of streamers martin scorsese's new film what happens at night we saw a first look at the movie today a still photograph of leonardo dicaprio and jennifer lawrence the stars walking down a driveway in a snowy background that's probably the image of the movie we'll be looking at for the next 18 months yes because it's currently filming in prague um do we normally get first looks for martin scorsese movies 18 months famously we did for killers of the flower moon there was that image of leo and lily gladstone at the table right and that was the only thing that we saw from the movie for …” “… her first streamer movie and Tarantino being the writer and producer of a of a big movie like this and he's like he really prizes theatrical right feels like an interesting rubber meeting the road moment for the studio we will continue to cover it i mentioned um speaking of streamers martin scorsese's new film what happens at night we saw a first look at the movie today a still photograph of leonardo dicaprio and jennifer lawrence the stars walking down a driveway in a snowy background that's probably the image of the movie we'll be looking at for the next 18 months yes because it's currently filming in prague um do we normally get first looks for martin scorsese movies 18 months famously we did for killers of the flower moon there was that image of leo and lily gladstone at the table right and that was the only thing that we saw from the movie for almost two years and then the movie came out okay i don't know when this movie is supposed to come out i presume in 2027 um i'm very excited for it obviously mustache and full effect for leo big fan looks looks good um i haven't read who's helping distribute this one what studio i think paramount did killers of the flower moon and warner's at f1 so …” View more
Ridealong summary
Martin Scorsese's new film, 'What Happens at Night,' is generating excitement even before its release, with a first look featuring Leonardo DiCaprio and Jennifer Lawrence. Set to film in Prague, the movie is expected to be a contender for the Oscars, potentially vying for Scorsese's second Academy Award. Fans are eagerly anticipating the film's release and the discussions it will ignite over the next two years.
The Big Picture · ‘Project Hail Mary’ Will Amaze! Amaze! Amaze! With Phil Lord and Chris Miller · Mar 20, 2026
Empty Netters Podcast
“… character names of an actor yep but i was initially thinking uh redford but it's not redford okay it's bob is it it's leo yes it's leo okay so it's leonardo dicaprio character names which is great bob is obviously one battle after another uh jordan belfort uh jay gatsby yep i would imagine um uh i i trying to figure out what oh jack dawson yeah okay i was like when is he gonna give you jack but i was gonna be so hard so i'll give you jack dawson yeah this is great okay calvin candy thanks for bearing with me everybody uh but this is great uh rick obviously calvin candy teddy daniels danny archer frank …” “… line so is this fuck me hold on i sorry everything fucking up right now what's fucking up me okay but you gotta think out loud okay i'm i'm thinking i don't i i don't have it okay i don't have it i was thinking it was potentially i mean these are character names of an actor yep but i was initially thinking uh redford but it's not redford okay it's bob is it it's leo yes it's leo okay so it's leonardo dicaprio character names which is great bob is obviously one battle after another uh jordan belfort uh jay gatsby yep i would imagine um uh i i trying to figure out what oh jack dawson yeah okay i was like when is he gonna give you jack but i was gonna be so hard so i'll give you jack dawson yeah this is great okay calvin candy thanks for bearing with me everybody uh but this is great uh rick obviously calvin candy teddy daniels danny archer frank abagnale jr and rick dalton phenomenal Leonardo DiCaprio” View more
Ridealong summary
Leonardo DiCaprio's characters are unforgettable, from Jack Dawson in 'Titanic' to Jordan Belfort in 'The Wolf of Wall Street.' In a lively discussion, the hosts rattle off a list of his most notable roles, highlighting the impact these characters have had on cinema. This playful exchange showcases the depth and variety of DiCaprio's performances throughout his career.
Empty Netters Podcast · Is Draisaitl's Injury Good For The Oilers And Blue Jackets On A Heater · Mar 19, 2026
The MeatEater Podcast
Ridealong summary
'Killers of the Flower Moon' is a cinematic masterpiece that captivated audiences, with striking imagery and a compelling narrative. Despite criticisms about its length, viewers found it engaging and memorable, making it a top contender for this year's Oscars. The film, starring Leonardo DiCaprio, has sparked discussions about its themes and artistic choices, leaving many eager to see it for themselves.
The MeatEater Podcast · Ep. 825: Snowflake Man and the Cadaver Otter | MeatEater Radio Live! · Jan 23, 2026

Top Podcasts About Leonardo DiCaprio

The Big Picture
The Big Picture
3 episodes
Adam Carolla Show
Adam Carolla Show
2 episodes
The Bill Simmons Podcast
The Bill Simmons Podcast
2 episodes
The Flycast
The Flycast
1 episode
The Rewatchables
The Rewatchables
1 episode
SmartLess
SmartLess
1 episode
Andrew Schulz's Flagrant with Akaash Singh
Andrew Schulz's Flagrant with Akaash Singh
1 episode
Handsome
Handsome
1 episode

Stories Mentioning Leonardo DiCaprio

Best Podcasts on Michael B. Jordan's Oscar Win
The 98th Academy Awards saw "One Battle After Another" take home multiple major awards, including Best Picture. Michael B. Jordan delivered a memorable speech after winning Best Actor for "Sinners." The telecast itself garnered mixed reactions, with discussions ranging from Hollywood's declining relevance to specific snubs, political commentary, and the perceived "Timothée Chalamet fatigue."
98th Academy Awards
Mar 17, 2026 · 13 clips · 8 podcasts