The Big Picture - The 25 Best Movies of the Century: No. 12 - 'The Wolf of Wall Street’

Episode Date: September 24, 2025

Sean and Amanda return to continue their yearlong project of listing the 25 best movies of the 21st century so far. Today, they discuss Martin Scorsese’s ‘The Wolf of Wall Street,’ starring Leonardo DiCaprio, a manic, exhilarating, wretched celebration of the worst people on earth set loose on an unwitting society. They explain why this was the official selection from Scorsese’s filmography, crown this as the greatest performance of DiCaprio’s entire career, and explore the infamous discourse revolving around whether or not the movie glorified its nefarious behavior. Hosts: Sean Fennessey and Amanda Dobbins Producer: Jack Sanders This episode is sponsored by State Farm®️. A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.®️ Learn more about your ad choices. Visit podcastchoices.com/adchoices

This episode is presented by State Farm, life's full of decisions, big and small, and sometimes you make movie ones you can really stand behind. For example, I was wise enough to stick around through the mid-credits during Ryan Coogler's sinners. And unlike my co-host, Amanda, I got to see a very special sequence with the great buddy guy, among other things. State Farm gets it. Making confident choices can make all the difference. That's why with the State Farm personal price plan, you can choose the right amount of coverage to help create an affordable price for you. a State Farm agent today to learn how you can choose to bundle and save with the personal price plan. Like a good neighbor, State Farm is there. Prices are based on rating plans

that vary by state. Coverage options are selected by the customer, availability, amount of discounts and savings, and eligibility vary by state. I'm Sean Fennessey. I'm Amanda Dobbins. And this is 25 for 25, a big picture special conversation show about the Wolf of Wall Street. Let me tell you something. There's no nobility and poverty. I've been a rich man and I have been a poor man and I choose rich every fucking time. Okay.

Yeah. The Martin Scorsese episode of 25 for 25 is upon us. Here we are. Only at number 11. We have once again made a huge mistake. This is just getting really stressful. So just a foreground this conversation. And we watched this movie last night and about it.

About 48 minutes into it, I texted you, is this the greatest movie ever made? Yeah. And it's a number 11 on our list. So we continue to make mistakes throughout this experience. This is the 23rd feature film for Martin. I did try to flip it at some point. Did you? I just want to say that I did try to flip it.

And you were like, no, I want to keep, you said I want to keep number 10 where it is. Okay. I don't even remember what number 10 is right now. Well, it's, you know, and I'm really looking forward to that one. Oh, yeah, yeah. And also, like, I was watching this movie and thinking about number 10. And I was like, these actually have a lot in common in their own way. Interesting.

No spoilers. So I feel good about it. Okay. But yeah, like we have Martin Scorsese's late career masterpiece at number 11 on this list. Like, we're stupid. We are stupid. I would like to foreground this conversation by saying that I have recently completed the five-hour Mr. Scorsese documentary that's coming to Apple in October. Directed by Rebecca Miller that is an extraordinary all-access look at his entire career and his life.

and features tons of collaborators, family members. There are so many things in this documentary that I have never heard about or seen revealed or seen shown with such intimacy. That's going to color this conversation and maybe some of my regret around its placement at number 11. Okay. Because this movie is simultaneously like the apotheosis of a style

and also a big outlier, I would say, in terms of his movies, because of its hyper-kinetic nature. Like, it's like the final boss of a thing he developed in the 21st century as a director. So, obviously, it is written by Terrence Winter, is based on Jordan Belfort, the famed, infamous trader, stockbroker, his memoir. It stars Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McCona, Kyle Chandler, Rob Reiner, John Bernthall, John Favreau, many others. Shot by the great Rodrigo Preeto. Give me some first reflections upon revisiting the movie.

I think this was our unanimous, not even a minute of conversation, Scorsese pick for this century. You know, obviously, so everything, and I can read what was eligible, which was... Some great films. Yeah, sure. Well, gangs of New York was not eligible. Well, I mean, it was eligible, but it was never in consideration.

Not considered, yeah. The aviator, not in consideration. The Departed, okay, Shutter Island, okay, Hugo, which you love, the Wolf of Wall Street, silence, which you made like a very half-hearted push for knowing... There is a real head's case for silence as another culmination of what he is interested in. Sure, and I understand that, and I respect it, and that is a real heads that are all male heads just sitting in a room. No, there are men and women who have had faith and have struggled with feelings about it. Right. I still see that as the movie that broke up Andrew Garfield and Emma Stone, which I do feel everyone's happy now.

Everyone's doing what they need to do. But in that moment, it was just Andrew Garfield was like, yeah, I just went method as a monk for three years or whatever. And that had repercussions. So that's where that is. There's no great art without great sacrifice. That's, I mean, that is what that movie is about over and over again. The Irishman, which I think is the most underrated film on this list. Okay.

And Killers of the Flower Moon, which is also a masterpiece. I think his last four films in particular are all incredible. Now, they are, he is in a very unique era of his career where a lot of his rise and fall and rise and fall is defined by that parabolic shape, you know, in the same. 70s, he's this kind of exciting new voice and the 80s things really dip and then he bounces back and then he goes back down again. He never totally gets told he's the best. Post-departed Best Picture win. Yeah.

It's become easier for him to get big movies made and he made this decision to make big movies on a grand scale like a lot of filmmakers from the 40s and 50s that he loves. So, you know, I would say Shutter Island Hugo, the Wolf of Wall Street, Silence the Irishman

and Killers of the Flower Moon, all of which are these kind of durational films. Yeah. They're all all about obsessions of his, whether it be filmmaking or faith, or the rot at the heart of the American soul. Yeah. You know, masculinity, anger, sex, all this stuff that he's always interested in. They're all... Drugs.

Abusing oneself, you know? Like punishing yourself, addiction, totally. They're all... Each one is about an individual thing, but they're also all about all of those things in interesting ways. So the Wolf of Wall Street, choosing it is funny. because I think it is the most by far conventionally entertaining of the movies from this period.

Yes, though, and we're already getting to the Desert Valorize, the behavior depicted versus desert. We should talk about it. But there is a lot. There are just a tremendous amount of naked women in this film I had forgotten, you know? And it really, it's like, it's at volume, you know? There is just like, what else can we put in here? And there is, you know, a grand, like, epic scale.

to the excess. That is the point. But is, you know, there were certain audiences who are just like, oh, wow, look at that. More tits. You know, that seems great. Yeah. I mean, it's 180-minute run time. It never takes its foot off the gas in terms of the Bacchanal that it's portraying that Belfort's life was this nonstop 24-7 exploration of how hard he could push himself into exploiting his body and his desires. Yeah. And that's what money drives him to do. do, and that's what money drives all people to do in this particular culture that we live in. So you could make the case that it is too much or that it was very popular because people didn't read the center of the message. I mean, that's, I would not, I would say that's not the filmmaker's

fault. If people only like this movie because it has a lot of tits in it, like we live in 2025. If you want to see tits online, you don't have to go watch a three-hour Martin Scorsese movie. It's pretty easy to get that done. It is also, the excess is the point. and is grotesque throughout the movie. And also there is, I mean, these people are just like true assholes, just real, real assholes. And so you watch their depravity and it shifts over the course of the three hours.

And at first you're like, I can't believe they're saying these things and it's sort of funny. And by the end, you are truly grossed out with them unless you are a person with no, you know, internal compass whatsoever and just enjoying it, which is your own problem. There are a few moments in this movie, though, that are very purposeful and very targeted where Belfort, who toggles between this sort of into camera delivery, where he's explaining how he feels about things and a voiceover that feels very much like a guy guiding his own, like shaping his own mythology. Yeah.

But he kind of breaks character a couple of times. There's one in particular where he talks about one of the stockbrokers that works at his his firm who marries one of the secretaries who blew him in an elevator. Right. And then they very quickly hop through their lives where they end up getting married. Yeah. And then she had turned out had slept with many of the men that she worked for that they all worked with. And then that guy committed suicide two years later.

Yeah. And we see this one shot of like his arm hanging over a bathtub and he's killed himself. There's one much later in the movie where we learned very quickly that Brad John Bernthal's character who's a drug dealer died of a heart attack at the age of 35. And then he compares him to Mozart. And he says, I don't know why that popped into my head. And there's just like these very quick revelations of like there's huge toll on doing this kind of thing. And it's not as simple as at the end you go to white collar penitentiaries. And then two years later, you're free and it's fine.

Like it's just that all of those things, we brush them under the rug the same way that we do in society. When something really bad happens, you know, we make a big deal of it. And then we go on to the next controversy or the next thing to distract us. The script is really, really smart about that stuff. But I think it's really unusual for the biggest movie star in the world to make a movie with this much access, with this much. I think of the first few things you see Leonardo DiCaprio's character do in this movie. That's a choice that he and Scorsese made,

and the movie was financed independently without a studio. Because I don't think a studio would have allowed for Leo to blow cocaine out of a prostitute's ass in the first five minutes of the movie. It's true. That's a bracing image from... The heartthrob of his generation. That's true. I can see it right now. Yeah.

Yeah. That big heart-shaped ass and the way Scorsese frames it. Yeah. I mean, in a way. But it's also like, here's what kind of movie you're watching. And so the idea that it was DiCaprio who went out and raised the funds to get this movie made from some uncertain financial figures. And a lot of that stuff came to light in the aftermath of this movie. But he raised $100 million.

Got Scorsese attached. attached this incredible cast and then the movie went on to be a huge hit. This is the biggest hit in Martin Scorsese's career made $400 million worldwide. So what is the lesson from that? Leo has good taste for one thing. And let great filmmakers do what they want

and the lesson from this movie and also that experience is that money usually, not usually, always does corrupt, but I guess sometimes you need it to do great things. Yes. Yes. I like that echo in the financing of the movie, which is, I don't know if it's nefariously financed, but there is some misdeed. Yes, exactly, around how the money was raised. And then that being a material part of the Stratton-Ovon story is so wonderful. It says everything I think you need to know about doing anything at scale in America, right? There's no way to do it cleanly. So the movie itself It very much is a Martin Scorsese movie

In that it is like Hard charging, very masculine A lot of desperation At the center of the Leave character Who's constantly trying to cloak it With this bravado Right The style of it

jumped out to me even more so Because it is like Roughly 80% montage Yeah I mean if you think about You do recognize the moments where it stops And it is just like Leo speaking into Whether literally speaking into camera

But also Leo as Jordan Belfort like having a moment And you're like oh it's this speech The first speech that you quoted At the beginning of that episode It's like everything stops And the camera He's in a room filled with people But it's not cunning way to everyone else

And you're on him for a long time That is true of He has a few speeches to the trading floor like that there is, when you text in me, I wrote back and I was like, I just watched the yacht scene, you know, which the first one, yep. But that is two people, that's Kyle Chandler and Leonardo DiCaprio, but they are memorable because there are moments when the movie and really the camera, like, actually stay in one place on two people as opposed to, you know, just literally every single thing that you can think of

that is a vice being crammed into one frame. Yeah, there's a couple of critical. scenes with Naomi. Margot Robbie's character, we can talk about her a little bit as well, since this is really her major breakthrough as a movie actress. One in particular where they're fighting when he's shirtless in bed and she keeps throwing the water on him. Oh, yeah, an all-time one. And then one near the end of the film, which is really, really upsetting when she decides to, she tells him that she's going to divorce him and his reaction to that, which is extremely ugly, like the absolute darkest part of this film. On purpose, you know? And the movie is building to that,

like this is really this is unsustainable and this is a person with real demons and this creates ugliness you're not supposed to celebrate him yes even still some people

didn't get that message but the movie knows exactly what it's doing you know we're not responsible for everyone online I totally agree and then I think on a grander well just let's go back

to the montage thing there are more than 30 needle drops in the movie yeah they are uh I would argue the pinnacle of him doing that and that the movie has this very weird

go-go-1950s and 60s blues soundtrack. In part, I think there's like a one, a very logical explanation for it, right? You hear Helen Wolfe's voice a bunch, this is the Wolf of Wall Street. There is a kind of like hungry, lascivious quality to some of those blues records that Scorsese and Robbie Robertson were obsessed.

And Robbie Robertson's career is like kind of sort of aping some of those records. But then there's also something very haunted about American Blues. And in particular, a series of scenes in this movie that I did, I talked about this at length on the rewatchables, but it is something that I know, I always think about when I watch this movie. There are moments where we get these slowed down blues songs during these incredible Bacchanalia moments where you can almost feel George. and like descending into hell or like or he's being portrayed as Satan right

and the the lighting in the scene changes the sound goes out you only hear the music and then the camera finds Belfort and he's like

looking at everything he has created and he simultaneously is gleeful but there's some weird regret or woundedness on DiCaprio's face

that's the paradise loss you know Satan yeah what have I done and but I mean it's a good point because like the reference is like a renaissance or something painting of yes you know of all of the the people cramden and i'm sorry my art history is failing me uh no it's a specific reference you know yeah yeah sometimes it's the last supper sometimes it's francis bacon and like the disgusting

nature of the human soul but all of this stuff is very intentional it's just it just feels very contemporary and funny the movie is very very funny and fun to watch it's but it's funny in a really fucked up way. Totally. And we've been talking a lot about what perfect timing this is going into one battle after another. And obviously

a lot of that is to do with the Leo of it all. But, you know, like Scorsese is a huge influence on all filmmakers, including PTA. And there is a like a really screwed up level

to the humor in this movie that is, that is very PTA as well of like, I'm asking you to laugh at some very uncomfortable things. And you will, but we all kind of know how hopefully we know how messed up this is. Yeah, I think the one thing that the two of them have in common, and that it seems like Leonardo DiCaprio is interested in, too, is the absurd lengths that powerful people will go to to make themselves feel better. And that often means mocking people or taking power from them. But then, you know, you put this here in the document, and I think

that it's true that this portrait of 80s excess and the rise of a certain kind of like... It is a 1980s conman who conquers America by reflecting back like what America actually is to itself. Does it ring any bells? And the use of lifestyles of the rich and famous and Robin Leach in this movie... There is a scene that takes place quite literally outside Trump Tower.

Yeah, and also the even the infomercial moment near the end of the movie where sort of like Jordan Belford is selling something not just to his investors, but to all of America about how to be better and more like him. This movie presages the locker room talk Donald Trump scandal by just a couple of years, you know? And it's undeniable that this era, especially of New York power, this is like the real gilded age where everything looks gold,

but it's copper underneath. And that is really what Belfour represents. Also, you know, this. This is such a very familiar tone of Long Island and Queens to me. And it is all of the personalities in the film. Like there's a moment where you see the cops come up to arrest Bernthal and Jonah Hill. And it's a, it's a Nassau County cop car. Yeah.

And I'm like, I grew up seeing that cop car all the time. Like, and they're in like this strip mall nearby. Yes, it all looks so familiar to me. So it is a weird reflection of my childhood in an odd way. Not that I was exposed to anything as crazy as this movie. but it does have a little bit of a personal connection for me as well. When you wrote down that note about the 80s con man, the quote from the movie that popped to me the most is,

I want you to deal with your problems by becoming rich. Yeah. Which is, I think, how a lot of people still feel. Yes. That this is a way to solve this unsolvable pain, and all the Scorsese movies are all about these unresolved pains. You know, the desire to be more famous, the desire to be more successful,

the desire to be a successful boxer, or the desire to be a successful gangster to be a comedian who gets to go on late-night television to just get through one night sleeping with the girl you want to sleep with. All of these fucked up guys in all these movies who are all trying to get something

that they think will help them feel better, but won't. Right. But do you know what I... A thing I really like about this movie is that that is absolutely what's going on, but it does not spend any time on the pain. Mm-hmm. Like, it doesn't...

There's no origin story. There's no trauma. You know, whatever. There's no, there's no really humanizing this person. I would see the only moments where you are necessarily drawn to Belfort because that is the type of character that he is. And the movie is exploring like what someone like this and what money and wealth and this display does to all of us.

I mean, it's literally the last shot of the film. But there are also moments where just like Leo... and the character like unlock a little something, there is a little bit of humanity. And you don't even know if you can really trust it, but, you know, it's the movie star thing. You're leaning in. But that is as far as it goes characterization-wise

of like of showing that there is someone or something going on in there. There's no attempt to like explain away the misdeeds and just like the grossness of the person. Totally. I would argue that that is something. that Scorsese does better than anybody. And then he very rarely falls into that trap. Like, if you think about Jake LaMotta or Rupert Pupkin

or the underground man and taxi driver, like... They just are as they are. They are the same as Jordan in that they are a product of their environment. Yeah. You know, like the world hits them and then they feed into it

and that that's it. That it is not like, oh, you know, you got beat up by our parents. And so you're like this now. Like, obviously, anybody, it's beat up by their parents is in tremendous pain, but that doesn't explain the decisions that they make in their life and in the world.

And I think he's very sophisticated about that. He doesn't try to engender sympathy, but that doesn't mean that these people aren't attractive in a way. Henry Hill is very attractive and exciting to watch in Goodfellas. Jordan Belfort is at times very exciting and funny in this movie.

It doesn't make him any less repugnant as a human because he's a disgusting person. But that dancing on that line and him still being able to channel this in, you know, I guess he's in his late 60s when he makes this movie is amazing. I mean, it's a movie that feels like it's made by a 30-year-old because of the amount of energy and pizzazz that it has, but also just a tremendous amount of human insight.

So it's where it stands, like even in his entire career is kind of a fascinating conversation. I mean, you and Adam Neiman and Chris did a Scorsese episode. And it was the one movie in all three top five. Was it? I don't remember. Maybe I'm misremembering, but it was in many of them and it was high. It would be in my top five as well.

I think, you know, everyone our age and younger gets it. I do think some of the older generation were a little, some of the people who were there in the 80s with Jordan Belford perhaps to not like the reflection back at themselves of what they were going through. There was a lot of writing about this. of criticism about this when the movie was released, this sort of idea. And he's obviously had to deal with this many, many times. He dealt with this in his portrayal of Christ. He dealt with this in his portrayal of young gangsters in New York

in the 1970s. Jack, I feel like this is a big Gen Z, young millennial movie. And I feel like for many people who are under 25, maybe their first Scorsese movie? 100%. Very big movie of people my age.

And if you want to talk about people not understanding the core themes and message, I mean, This is a prime frat dude dorm poster movie. Yeah. I mean, just completely misreading it, which is unfortunate, but I mean,

it's an all-time favorite of mine. It's amazing. It's not the movie's fault, you know? Well, I do think... We live and we learn. Hopefully we grow. There's no way to know this, but let me just speculate.

Do the producers of the movie know that they're going to be able to make this a very profitable affair because of what the stuff that they're putting in the movie? Even knowing in their heart of hearts that this is an artistic journey to show that there's something rotten at the center.

Do all the producers know that now that we know the list of the producers? Are they all like, yeah, this is about like, you know, how money is evil? I don't know whether they do. Maybe they're thinking a lot. They're like, sure, more drugs. Yeah, let's really get into the specifics of the pharmaceutical grade of Kualudes. You know, let's explain those to the people. That stuff is unbelievable in the movie. That whole sequence is a wild Buster Keaton-esque misremembered genius moment. Let's talk about the Leo performance. Let's do it. So you have written here that this is the single greatest performance in Leonardo DiCaprio's career. It is. I'd like to unpack that with you. Okay. Now, as much as this is a Martin Scorsese pick, this is a Leo pick for us.

Leo in the 21st century has made 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 16, 17, 18. This is like watching my son count right now. One battle after another will be either his 19th or 20th feature film this century. You can count to 20. Congratulations. In fact, I counted to 20 in Spanish with my daughter last night. Yeah. At her request. Knox gets thrown off at 14.

You know, then things get dicey. Yeah, Catoose. So we're not talking about one battle after another yet. Yeah. And I'm not suggesting it's his best performance of the century, but it may come up. Yeah. And that may come up as a discussion point. I think

I'll I'll reflect on this career right now because this is a really worthwhile conversation and in that Scorsese documentary that I cited Leo kind of arrives into the movie

at Gangs of New York and Gangs of New York had been a long time passion project for Scorsese he'd been trying to get it off the ground since the late 70s and it took a really long time

to do it does that ever go well by the way when someone's been trying to get a project off the year off the ground for like 30 to 40 years? I mean, PCA's been trying to get one battle off the ground for 10 years. Sure. Once we get into 30?

Yeah, sure. Yeah. Well, the world changes. The world changes. Sure, but I just like, let's look back, even like our greatest filmmakers. Has anyone been like, yeah, that was it. I nailed that. Megalopolis. Right. That's what, exactly. I think you're right that once you get past a certain timeline. Sure. Gamel Dator has been trying to make Frankenstein for 30 years. Well, sir. That's a very good topic of discussion for the Frankenstein. and sign episode.

The Passion Project top five. Anyway, Gangs of New York was never going to be on our list. It was no. And it's an interesting one because Leo desperately wanted to attach himself to Scorsese. He idolized Scorsese.

He tells this great story. He met De Niro working on this boy's life and he watched every De Niro movie. And he really connected with the De Niro Scorsese movies. And that was how he really got hit

to Scorsese. And he made it his mission after Titanic to get Scorsese movies. And he has been good to his word including his next movie apparently is going to be another Martin Scorsese movie

so they've been on this journey together for 25 years Gangs of New York you could argue is one of his worst performances Yes He's a little miscast But I would never take anything away from that movie Because if he doesn't make it Then you don't get the departed

You know and you don't get Shutter Island And you don't get all these much more interesting Leo performances Anyhow Let's set aside Titanic And Romeo Juliet for a second Because I don't you know He's still he's a young pup

He's wonderfully effective in those movies. Other movies in contention for the best Leo performance of the century. Okay. I will suggest Django Unchained. Okay. As Calvin Candy, one of the great villains

of the last 20 years, and he is, he just pulls no punches in that movie. Right. He is as vicious and unsparing as, I would argue, any major movie star has ever been in a Hollywood production.

Okay. The things that he says and the things that he does, that was a really fucking brave move on his part, and it led to, I think, and, you know, he had previously also just played Jake or Hoover. Like, he clearly is not afraid of complicated,

not nice people in American history. The movie that he won the Academy Award for is the Revenant. Yeah. Which is a great physical performance. Who cares? So is this! I agree.

He wore a bear, you know, whatever. He did a lot of other things. I think that was a very hard movie to make. It obviously is not the movie I would have. given him the... Now, I could argue that once upon a time in Hollywood is his best performance.

Yeah. I mean, it has a couple virtuos, so scenes, obviously the, what is the name of the TV show? Bounty Law. Like the bounty law scene where he starts crying. Yeah, you know, I get it. He's on the set of a different show, actually, when he does that.

Yeah, that's when he's playing as like a day player opposite Tim Oloffin. Yeah. But him in the trailer breaking down, that's going to be near the top of his reel at the end of his career. Sure. But I would see that Quailudes will and should also be at the top of my reel. Okay. You know? Yeah. I had forgotten the dancing at the wedding.

I love that. I almost like to you about that too. You know, it's like. Again, dancing to a 60-year-old blues song. It's so incongruous. It's not, like, it's not, you know, some people will pop out the moves. the time and that's not something Leo does over and over again. I was like, I didn't know you

could do this. Like, where did you learn to do this? He's just so loose in the movie. The whole movie, he's not tight. I find a little sometimes with him, he can be a little tight as a performer, a little mannered. He's very, very loose in one battle after another. He's very loose in once upon a time in Hollywood, and he's very loose in this movie. And he's good

that way. Yeah. You know, he's in the middle of a really interesting run of films where he's constantly playing this kind of comic drama yeah you know and I didn't include this movie when I was thinking about this

because the Revenant came right after it but this movie is in the same league with Once Upon a Time in Hollywood Don't Look Up Killers of the Flower Moon and one bad after another where he's getting a lot of laughs in the movie you would not have said that about him

around the time of like no he was too sole serious and a body of lies and revolutionary roads like these are heavy movies and he has really pivoted in this interesting way 40s and 50s now. He's just turned 50 last year into doing this different kind of thing.

But I think you're right that this is, because the movie is so big, so long, he's at the center of every single moment. He's asked to do extraordinary physical stuff. Right. Laugh lines. He's got to have strong emotionality. He's in full con man mode.

And also just have enough vulnerability so that we all know. Right. This guy's fucked up. Everything he's doing is wrong. But we don't want just turn it off. Well, like Henry Hill, he is also, the movie is about him, but he is our way into the movie. Like, he is the narrator, but you're also watching him be at lunch with Matthew McConaughey.

You're watching his transformation and watching him see this world and then lose himself to the world. So he's got to communicate like the longing and almost the connection to the audience as well as like the total grossness and you know and he also has to be able to sell that last scene and which you know this scene is really about the shots of all the people watching him but there is like a sell me this pen you're referring to yeah some of this pen but there's like a queasiness and uh am i rooting for him like am i like is this a store is this do we want him to Is this punishment?

Like, what is this failure? What is this? That is, I mean, he has to be everything. He has to be the villain and the hero of the movie. So I don't know. It's pretty complete as a performance.

I agree. And you put your finger on something else that I wanted to talk about that I think is so interesting. So you mentioned that yacht scene when Kyle Chandler boards the yacht and they're sort of having this very friendly but tense

walk through of what their relationship is going to be and whether or not he's going to be pursued by the FBI. And he's trying to make some moves feel out whether or not he's going to be able to bribe these guys. And by the end of the scene, I was rooting for Leo. Yeah.

Because the government is impinging upon a self-made person and trying to tell them that they can't run their business the way that they want to. Now, that person who is doing that is breaking the law and also taking advantage of helpless people and a very broken system. And also the story that he tells. to effectively attempt to bribe Kyle Chandler's FBI agent results in the mom not living through the surgery that, you know, it's like we helped this guy get a, you know, an overnight deal

so that he could pay for his mom's like heart surgery. And it was very sad she didn't survive. But anyway, what a fuck it's so funny. It's incredible, amazing messed up scene. But by the end of that scene, when Chandler and his colleague are leaving the boat and Belfort starts yelling at him about how you're going to be riding the subway home we do have that payoff moment

near the end of the movie where we do cut to Kyle Chandler and he sees the headline about Belfort after he's been arrested and sentenced to prison time and he has a quiet moment of reflection about what his life is and what he does and what the FBI represents and what government work is

and it's very modest but most movies would not show that and they would not show that there is like a nuance and a complexity to this issue and that what Jordan Belford is doing is the work of someone who's trying to get a leg up on other people so that he can have what he wants

and that the government thinks that there is a kind of nobility in the work that they do. But it's not all roses. They're corrupt too or they also have this kind of like bottomless existential dread of am I wasting my life

if I'm not succeeding. You know what I had forgotten is when they do finally raid Stratton-Okmont. The needle drop is the, the Lemonheads, Mrs. Robinson, which I would also like to, like... How did that happen? How do Marty and Robbie Robinson

become, like, aware of the limit, you know? There's some funky ones in this movie. What's this process? But it's, I mean, it's just an absolutely like pitch perfect, very funny, jarring needle drop. But even there, it's like, you know, and everyone in their windbreakers and it's just like, well,

this is all fucked. No one is... Yeah, and I think if you want... It's plastics for everyone. It's exactly right. I was going to say, I think if you want to draw it all the way out, you can be like, well, this is the copy of a moment of cultural revolution. And it's like, it sounds close to it, but it's not really it. And this is, you know, Jordan Belford is not Andrew Carnegie.

You know what I mean? He is not, like, he didn't invent anything. He just kind of took advantage of this moment in history. So there's so many clever little moments like that throughout the movie, and especially with the music, which I still think is so phenomenal. Can I just suggest one? possible contender for the best Leo performance. Sure. Catch me if you

can. I was surprised that you skipped over it when you were reading all the things. It is really good. I wanted to come back to it as like, to me, this is maybe the runner up to Wolf of Wall Street. Yeah, well, it's very similar, but just like a lot more daddy issue, Christopher Walk, and stuff, which, you know, pays off in the scenes with Tom Hanks, America's

dad. But yeah, it's good, but this is that's young Leo. I think that's like, well, that's of the generation of Titanic. It is. I feel like it's the springboard movie. I feel like it's the movie where he learns how to give a more mature performance.

So it's at least important. Yeah. I really love that movie. It does have some of the trappings of explaining why someone is the way that they are that we're talking about that you don't necessarily have to do. And sometimes you need to. But I just, I think it's like a very novel feat of this film that it doesn't. And, you know, Spielberg is obviously prone to. Daddy Issues movies, so it happens.

One other thing I wrote down here, this movie essentially breaks every rule. So I mentioned the into-camera explanations and the voiceover. It breaks the fourth wall and it explains everything to you. It's an unreliable narrator, which is not that's a good thing often in films like this, but still, these characters are pretty one-dimensional.

Yeah. Most of the people in his cohort, even Donnie Azov, Jonah Hill, who's phenomenal in this movie. super funny and pitch perfect in a lot of ways not a lot of nuance to these guys

like they want something they have a they're hungry wolves I'm sorry I'm just thinking about all the funny things Jonah Hill does in this movie it's an incredible performance the teeth

the way that he's styled his hair the glasses all of the costume they're running away from Bernthal and the strip mall the I mean all the cousin scene you know at the bar

it's it's really good Steve Steve Madden The casting across the board is really good. Also, just for the 90s women in my life, of which there are no one listening to this podcast, like Steve Madden being a crucial figure of this movie is just very important. Yeah, obviously it is true to the story of Jordan Belfort,

but it is a perfect stand-in. I will say, as a 12-year-old or whatever, living on Long Island, going to the mall and trying to understand why every girl I knew needed to have Steve Madden's shoes while looking at the shoes. Yeah. It didn't make sense. Yeah, but we did.

And now it does make sense. We did. You know? Does that make you feel any worse about the industry of fashion and style trends that the people at the levers are these monsters? I don't know. Just David Ellison owning all of Hollywood make you feel any worse about your DVD collection?

Yeah. Okay. All right. Well, it makes me feel worse about the future. I don't know about the past. I mean, he didn't do anything with the past. Yeah. No.

I mean, I have larger concerns with the fashion industry. Okay. What are they? Well, you know, how we're treating workers and obviously sustainability and all of that stuff. Like, where are all the Steve Madden shoes that I wore in the 90s? They are not decomposing somewhere. Yeah, they're not made of natural materials. How many pairs of Steve Madden shoes did you own? Well, so I had the loafers and I had them in like the four inch height and the,

the two-inch height. Okay. Did you tower over all these poor young boys when you were like 13? Yeah, of course. Like, what's the alternative? And it's not my fault that...

We're flats. Yeah. Well, I had the two-inch as well. Okay. But the chunky four-inch, low for heel. If Jack, Google this so that you can understand the reference,

all right, we got a thumbs up from Jack. Don't Google it. This was really, listen, this was like 17, like magazine, Delia's era. It was very important. I remember. But I probably did,

go through like a couple of them because you wear them out wear and tear yeah sure and it's not exactly like they're made

for a lifetime except for when it comes to landfills well Steve Madden thanks you for your service even though his pump and dump scheme led to him

being deleted from the fashion industry for a stretch of time yeah I think gosh is this the right choice

for Scorsese I think it is what Would you want silence? You know I was never going to do silence. I know. I haven't gone back to silence. I would like to see silence again on a big screen. I saw silence before this show started in a movie theater, you know, regular paying crowd by myself on Christmas Eve. And like in the morning. Yeah. It was like the movie event of the year for me. No, I think I saw it at the arc light by myself. I would have said it was like the week before Christmas, but now that I'm thinking, about it. Maybe it was the week. It might have been the week before. Because you had seen it and then our friend Gilbert Cruz had seen it and I texted

and were like rapturous and I texted each of you being like okay boys. It was December 23rd, 2016 is when it opened. Oh, okay. So it must have been like that after Christmas vibe. I saw I'm sure I saw it the day came out and you know I really flipped over it

and I've watched it one time since then. Okay. But it is similarly a very big long movie with a lot of big ideas in it. But silence gets some time in this Apple documentary. I think because it's a very important movie to Scorsese. So, yeah, I never thought you would go for it. I do think this is a perfect meeting ground for us in a lot of ways. It's wonderful to celebrate Leo in this way. I think the Irishman is also would have been worthy of exploration. It definitely would have been worthy of exploration. I think that movie is much more divisive. There are a lot of people who do not like

it. People are wrong. Some people can be wrong. Yeah. That's not their list. It's our list. Are you saying you're never wrong? When I am wrong, I say I was wrong. But it is pretty rare. You've made yourself so lovable. Recommend it if you like.

Did you write these down? I did, yeah. This is funny, right? Because I like what you've written down here. Boiler room, margin, call, and industry. That was just all on one. list. I don't know. If you like, if you like these movies about how all the finance bros are living the good life, but also maybe not, you know, then this is the ultimate. This is, you know, the

mothership. Yeah. Well, I think also Wall Street, Oliver Stern's film is also probably a part of this lineage of these kinds of movies and TV shows. And gets a name check in Wall Street. He does. He does. That movie feels very small compared to Wolf of Wall Street. You know, it is a big movie. But also the second half of it is kind of like what's going on. There's stuff in it that. It's not my favorite. When we did our Stone episode, it's not really high for me personally. But yeah, I mean, boiler room, I guess the next one, too, the big short is also, these are all part of a story of American finance.

I think we also didn't really talk about this movie came out in 2013, which was pretty soon after the 2008 crash. And definitely at the time felt like, if not a response too, then like in conversation, like yet another piece of like, oh, this is what they're up to on Wall Street. Yeah, Leo got Warner Brothers to acquire the rights to Belfort's memoir in 2007. And they started developing the movie in 2010 as a direct response to everything that was happening at that time. And so you can very clearly see the movie as this rejoinder to this terrible moment in American history. And also, Margot Robbie in a bathtub and direct-to-camera speaking about financial things and, like, simplifying them. You know, it is all right there.

They're really twinned in a lot of ways. You could argue that I like the big short. I do as well. The one turned out of McKay, you know, for a variety of reasons. But I still think that those couple of first few, like, sociopolitical comedies that he made are really good. but there is a lot that the Wolf of Wall Street accomplishes that obviates some of the big short as well

that kind of like accomplishes a lot of what it's trying to say there is some more specificity in the big short but I agree with you it's a great shout and then you've listed one battle after another and you know we're we're 24 hours out from the movie event of the year

I know I'm very excited I am too you're a little nervous you're feeling the pressure I want to do a good job on our episode I do as well I, I, this very rarely happens. The last time this happened was once upon a time in Hollywood.

Okay. Where I was like, I've been waiting for this all my life. Yeah. I've been waiting for somebody whose work I care about this much, who I know has made, done something special. I remember the, I remember being at the first screening. It was at the arc light of once upon a time in Hollywood. I was so psyched to be invited to that screening. And as soon as it was over, I was like, forever movie.

That's a forever movie. Yeah. That's like the best feeling in the world. plenty of great films since then. Plenty of films I've given five stars to. But when you've seen something that you know is special, if you have a platform like this, I want to do a good job.

So we will do that job very soon. Thanks to Jack Sanders for his work on this episode. Number 10 is also a wonderful movie that I am very excited to revisit, and I have not seen in a long time. I'm psyched. I can't wait. It's an Amanda movie. It's an Amanda movie.

And that'll be, is it next week? It's next week, right? I don't know, Jack? October 1st. Okay. It's next week. We'll see you then.