The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’

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0:57I'm Sean Fennessy. 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 in 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. And only at number 11. We have once again made a huge mistake. This is getting really stressful. So just to foreground this conversation, we watched this movie last night. And about 48 minutes into it, I texted you, is this the greatest movie ever made?

1:34Yeah. And it's at 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. 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.

2:02No 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.

2:40That'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 hyperkinetic 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 stars Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McConaughey, Kyle Chandler, Rob Reiner, Jon Bernthal, Jon Favreau, many others.

3:23shot by the great Rodrigo Prieto. 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 that it was - There is a real heads case for Silence.

4:09There's a real - 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.

4:51There'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, 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 70s, he's this kind of exciting new voice. In 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.

5:31Post-departed Best Picture win, 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. They're 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 abusing oneself, you know, like what, like punishing yourself, addiction.

6:13Totally. 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 it, 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 valor, you know, valorize the behavior depicted versus. 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?

6:50And 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 runtime. 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. Right? And that's what money drives him to do, and that's what money drives all people to do in this particular culture that we live in.

7:28So 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. It is also the excess is the point and is grotesque throughout the movie. 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.

8:13And 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.

8:47There's one in particular where he talks about one of the stockbrokers that works at 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 she had turned out had slept with many of the men 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 learn very quickly that Brad, Jon Bernthal's character, who's a drug dealer, died of a heart attack at the age of 35.

9:19And 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. 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.

9:58With this much like think of the first few things you see Leonardo DiCaprio's character do in this movie. It's true. 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. It's true, I can see it right now, yeah. Yeah, that big heart-shaped ass and the way that Scorsese frames it. Yeah. I mean, in a way. But it's also like, here's what kind of movie you're watching.

10:33And 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.

11:24Yes, 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-Oklan 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 lead 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.

12:27And you're like, oh, it's this speech. The first speech that you quoted at the beginning of the episode is like everything stops. and the camera, he's in a room filled with people, but it's not cutting away 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 texted me, I wrote back and I was like, I just watched the yacht scene, you know, which the first one. 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.

13:03Yes. 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. Yes. when she decides to, she tells him that she's going to divorce him and his reaction to that, which is extremely ugly.

13:37Right. Like the absolute darkest part of this film. On purpose, you know? Totally. 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. Exactly. 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. Listen, you can't, you know, we're not responsible for everyone online. I totally agree. and then I think on a grander well just to go back to the montage thing there are more than 30 needle drops in the movie yeah they are 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 one a very logical explanation for it right you hear Helen Wolfe Wolf's voice a bunch.

14:31This 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 with. 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 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 Jordan descending into hell or he's being portrayed as Satan.

15:16And the lighting in the scene changes, the sound goes out, you only hear the music, and then the camera finds Belfort. And he's looking at everything he has created. And he simultaneously is gleeful, but there's some weird regret or woundedness on DiCaprio's face. It's the paradise lost, you know, Satan. What have I done? But I mean, it's a good point because like the reference is like a Renaissance or something, painting of, you know, of all of the people crammed. And I'm sorry, my art history is failing me. No, it's a specific reference, you know. Yeah, yeah, yeah. Sometimes it's the Last Supper.

15:56Sometimes it's Francis Bacon and the disgusting nature of the human soul. But all of this stuff is very intentional. It just feels very contemporary and funny. The movie is very, very funny and fun to watch. 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.

17:03Yeah. 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 con man 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 even the infomercial moment near the end of the movie where sort of like Jordan Belfort is selling something not just to his investors, but to all of America about how to be better and more like him.

17:46this 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 Belfort represents. Also, you know, 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 Nassau County cop car. And I'm like, I grew up seeing that cop car all the time.

18:30And 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. refresh your good vibes mit Tic Tac mit den richtigen Vibes wird oh man zu

19:03jetzt probieren die verschiedenen Tic Tac Sorten von minzig frisch bis fruchtig süß Tic Tac refresh your good vibes 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 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.

19:46All of these, all 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 isn't, there's no origin story, there's no trauma. It's true. you know, whatever. There's no really humanizing this person. I would say 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.

20:32I 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.

21:10And 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 your parents. So you're like this now. Like, obviously, anybody who gets 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.

21:48He doesn't try to engender sympathy, but that doesn't mean that these people aren't attractive in a way. You know, 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 a where it stands like even in his entire career is kind of a fascinating conversation I mean, you and Adam, Naiman, and Chris did a Scorsese episode, and it was the one movie in all three top fives.

22:41Was it? I don't remember. Maybe I'm misremembering, but it was in many of them, and 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 Belfort perhaps did not like the reflection back at themselves of what they were going through. There was a lot of writing about this, a lot 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.

23:15He 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 I mean just completely misreading it which is unfortunate but I mean it's an all time favorite of mine 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.

23:54Do the producers of the movie know that they're going to be able to make this a very profitable affair because of 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 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 Quaaludes. You know, let's explain those to the people.

24:27That 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, 9, 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.

25:10You 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, 14.

25:25So, 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, it might. And that may come up as a discussion point. I think... Okay, 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. Yeah. And Gangs of New York had been a longtime 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 ground for like 30 to 40 years?

26:05I mean, PCA has 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 yep 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 Guillermo del Toro has been trying to make Frankenstein for 30 years well sir that's a very good topic of discussion for the Frankenstein episode the passion project top fives anyway Gangs of New York was never going to be on our list it was no No, and it's an interesting one because Leo desperately wanted to attach himself to Scorsese.