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

Summary

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

Host: Sean Fennessey & Amanda Dobbins
Date: September 24, 2025

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Episode Overview

In this episode, Sean Fennessey and Amanda Dobbins take a deep dive into Martin Scorsese’s The Wolf of Wall Street, ranked No. 12 in their “25 for 25” series celebrating the 25 best films of the 21st century. The hosts reflect on the movie’s legacy, Martin Scorsese’s late-career masterpieces, and Leonardo DiCaprio’s iconic performance, while also weighing in on the film’s controversial reception, comic excess, and cultural significance following the 2008 financial crisis.

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Key Discussion Points & Insights

Placement and Scorsese’s Oeuvre

• Both hosts are self-deprecating about ranking The Wolf of Wall Street at No. 12, frequently joking about their “mistake” and questioning its placement (02:05, 02:36).
• Contextualizes the film among other late Scorsese works (Shutter Island, Hugo, Silence, The Irishman, Killers of the Flower Moon), emphasizing Scorsese’s current era as one marked by obsession, masculinity, excess, faith, and self-punishment (05:37).
• Amanda:

  “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.” (05:37)

The Film’s Hyperactive, Excessive Style

• They point out that the movie’s hyper-kinetic, montage-driven style is both the culmination of Scorsese’s career-long fascination with excess and an intentional critique (04:46).
• The runtime (180 mins) is packed with relentless depictions of debauchery:

  “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...” (07:34)

Moral Ambiguity and Audience Reception

• Address frequent debate: Does the film celebrate or critique Jordan Belfort’s behavior?
• Amanda:

  “There is a grand, like, epic scale to the excess. That is the point. But… there were certain audiences who are just like, oh, wow, look at that, more tits. You know, that seems great.” (06:58)

• Both agree Scorsese is not endorsing Belfort, instead showing the grotesque costs; many audience members missed the critique (08:19).
• Sean:

  “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.” (07:34)

• Amanda highlights the purpose behind shocking or tragic story beats:

  “The excess is the point and is grotesque throughout the movie … you are truly grossed out with them. Unless you are a person with no, you know, internal compass whatsoever...” (08:19)

Narrative Technique & Structure

• The film is “roughly 80% montage” with a series of memorable, static speeches that break through the constant motion—such as DiCaprio’s rousing trading floor monologues and the pivotal yacht confrontation with Kyle Chandler (12:44–13:22).
• The film expertly uses unreliable narration, direct address, and voiceover to craft Belfort’s myth and signal, at times, the dark consequences lurking beneath the bravado (08:56).

The Musical Dimension

• 30+ "needle drops" (soundtrack cues) are used masterfully; often, blues tracks underscore Belfort’s descent, suggesting his own awareness (or lack thereof) of his moral failings:

  “There are moments where we get these slowed-down blues songs during these incredible bacchanalia moments… you can almost feel Jordan, like, descending into hell…” (15:46–16:07)

Parallels to American Finance & 80s/Trump-Era Success

• The film’s vision of hedonistic, predatory capitalism is described as both a portrait of 1980s greed and a harbinger of Trump-era politics.
• Amanda:

  “It is a 1980s con man who conquers America by reflecting back, like, what America actually is to itself. Does it ring any bells?” (17:46)

• Use of pop culture artifacts—Lifestyles of the Rich and Famous, Trump Tower, etc.—ties the narrative to contemporary America (18:02).

Personal Reflections & Long Island Authenticity

• Sean shares how the film’s depiction of Long Island and finance culture resonates with his own upbringing (19:00).

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Notable Quotes & Memorable Moments

• On why Scorsese and DiCaprio made such an excessive film:
  Sean:

  “The idea that it was DiCaprio who went out and raised the funds to get this movie made from some uncertain financial figures... And then the movie went on to be a huge hit. This is the biggest hit in Martin Scorsese's career. It made $400 million worldwide. So what is the lesson from that?” (10:53–11:32)

• On the movie’s moral center:
  Amanda:

  “You're not supposed to celebrate him.” (14:19)

• On the nature of the film’s characters:
  Sean:

  “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.” (22:53)

• On generational legacy and misunderstandings:
  Sean:

  “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's movie.” (24:34)

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In-Depth: Leonardo DiCaprio’s Performance

Why It's Leo’s Best Performance

• Amanda calls it “the single greatest performance in Leonardo DiCaprio’s career.” (26:11)
• They review DiCaprio’s 21st-century roles, ultimately agreeing that his hyper-physical, comic, and tragic embodiment of Belfort is unmatched (26:04–32:29).
• Amanda:

  “He has to be everything. He has to be the villain and the hero of the movie. So I… it’s pretty complete as a performance.” (33:26)

• Praised for physical comedy (the famous “quaalude crawl”) and unguarded looseness:
  Sean:

  “He's just so loose in the movie, the whole movie. He’s not tight. … He’s very, very loose in one battle after another [and] in Once Upon a Time in Hollywood and he's very loose in this movie.” (31:03)

Memorable Scenes Highlighted

• Quaalude overdose sequence:
  Amanda:

  “I would say that Quaaludes will and should also be at the top. It’s at the top of my reel.” (30:34)

• Dancing at the wedding (31:03).
• The “sell me this pen” penultimate scene as a metaphor for American success myths (33:18–33:26).

Comparison to Other Leo Roles

• Django Unchained, The Revenant, Once Upon a Time in Hollywood, Catch Me if You Can are all considered, but none match the range or bravado of Wolf of Wall Street (29:33–37:07).

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Film’s Context & Cultural Resonance

Connected Films & Genre Tradition

• Places The Wolf of Wall Street alongside Boiler Room, Margin Call, Industry, Wall Street, and The Big Short as essential entries in the canon of American finance corruption and hubris (43:08).
• Amanda:

  “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.” (43:18)

• Direct connection to the 2008 financial crisis and a resurgence of financial thriller/black comedy movies (44:07).

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Additional Noteworthy Aspects

• Breaks cinematic rules: fourth-wall breaking, unreliable narrator, one-dimensional side characters, and gleeful, outrageous tone (38:04).
• Jonah Hill as Donnie Azoff: Highlighted as an “incredible horse” with particular praise for physical comedy and his role as Belfort’s wild counterpart (38:34–38:49).
• Margot Robbie’s breakout: Her performance, especially in the emotionally-charged final confrontations, is discussed as a major breakthrough (13:43–14:09).
• The Steve Madden subplot: Both comic and authentic, drawing on 90s nostalgia and Long Island culture (38:49–39:28).

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Timestamps for Key Segments

• [04:46] Scorsese’s late style, context among his 21st-century films
• [07:34] The film’s structure and moral ambiguity
• [13:20] Standout scenes: trading floor monologue, yacht with Chandler
• [15:46] Use of blues music and “descent into hell” moments
• [17:46] 80s conman roots and parallels to Trump-era America
• [26:04] Why DiCaprio’s performance is his best
• [33:18] The “sell me this pen” and the American myth
• [43:08] “Recommended if you like...” other financial corruption movies

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Closing Thoughts

• The hosts reaffirm The Wolf of Wall Street as the definitive 21st-century Scorsese, the best and most complete Leonardo DiCaprio performance, and a vital reflection of modern American greed and absurdity.
• Discussion ends with anticipation for the next entry in the countdown and a light tease that an “Amanda movie” is up next (46:36).

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"This movie essentially breaks every rule. ... 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."
— Sean Fennessey (37:50)

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For fans of:

• High-octane black comedy
• Scorsese's maximalism
• Deep-dive character studies of antiheroes
• Films interrogating the American Dream and financial malfeasance

Essential context:
The Wolf of Wall Street remains a cultural touchstone—a film both exhilarating and damning, both endlessly rewatchable and deeply discomforting, and a defining work for two major American film artists in the 21st century.

Transcript

[A]

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 a 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. Talk to 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. A message from McAfee.

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[A]

I'm Sean Fennessy.

[B]

I'm Amanda DOBB.

[A]

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 have been a rich man and I have been a poor man and I choose rich every fucking time. Okay.

[B]

Yeah.

[A]

The Martin SCORSESE episode of 25 for 25 is upon us.

[B]

Here we are only at number 11.

[A]

We have once again made a huge mistake.

[B]

This is getting really stressful.

[A]

Just to foreground this conversation, I rewatched this movie last night and about 48 minutes into it, I texted you, is this the greatest movie ever made?

[B]

Yeah.

[A]

And it's at number 11 on our list. So we continue to make mistakes throughout this experience. This is the 23rd feature film.

[B]

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.

[A]

Okay. I don't even remember what number 10 is right now.

[B]

It's, you know, and I'm really looking forward to that one.

[A]

Oh, yeah, yeah.

[B]

And also, like, I was watching this movie and thinking about number 10, I was like, these actually have a lot in common in their own way.

[A]

Interesting. No spoilers.

[B]

So I, I feel good about it.

[A]

Okay.

[B]

But yeah, like, we have Martin Scorsese's late career Masterpiece at number 11 on this list. Like, we're stupid.

[A]

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. Because this movie is. 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 Terence 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 shot by the great Rodrigo Prieto. Give me some first reflections upon revisiting the movie.

[B]

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.

[A]

Which was some great films.

[B]

Yeah, sure. Well, Gangs of New York was not eligible. Well, I mean, it was eligible, but was never inconsideration.

[A]

Not considered. Yeah.

[B]

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 heads.

[A]

Case for silence.

[B]

There's a real.

[A]

As another culmination of what he is interested in.

[B]

Sure. And I understand that and I respect it. And that is real heads that are all male heads just sitting in a room.

[A]

No, they're men and women who have had faith and have struggled with feelings about it.

[B]

Right. I still see that as the movie that broke up Andrew Garfield and Emma Stone, which, like, I do feel, you know, 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.

[A]

There's no great art without great sacrifice.

[B]

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, and Killers of the Flower Moon, which is also a masterpiece.

[A]

So 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 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. They're all about obsessions of his, whether it be filmmaking or faith or the rot at the heart of the American soul. Masculinity, anger, sex, all this stuff that he's always interested in. Drugs, drugs, abusing oneself, you know, like. 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 it. I think it is the most by far conventionally entertaining of the movies from this period.

[B]

Yes, though. And we're already getting to the. Does it valor, you know, valorize the behavior depicted versus we should talk about it. But there is. 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.

[A]

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 non stop 247 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. 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 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.

[B]

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. 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.

[A]

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. 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 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. 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. And we see this one shot of 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. And then he compares him to Mozart and he says, I don't know why that popped into my head. And there's just these very quick revelations of 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, 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 excess, with this much like, 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.

[B]

It's true.

[A]

That's a bracing image from the heartthrob.

[B]

Of his generation right now.

[A]

Yeah, yeah. That big heart shaped ass. And the way Scorsese frames it, 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 yeah, 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. I made $400 million worldwide. So what is the lesson from that?

[B]

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.

[A]

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 are some money. Yes, exactly. Around how the money was raised. And then that being a material part of the Stratton Okmon 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.

[B]

Right.

[A]

The style of it jumped out to me even more so because it is like roughly 80% montage.

[B]

Yeah.

[A]

I mean, if you think about.

[B]

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 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.

[A]

The first one. Yep.

[B]

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.

[A]

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.

[B]

Oh, yeah. An old time one.

[A]

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.

[B]

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.

[A]

Exactly.

[B]

You're not supposed to celebrate him.

[A]

Yes. Even still, some people didn't get that message. But the movie knows exactly what it's doing.

[B]

You know, we're not responsible for everyone online.

[A]

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.

[B]

Yeah.

[A]

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 a one. A very logical explanation for it. Right. You hear Helen Wolf'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 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, like, descending into hell or like. Or he's being portrayed as Satan.

[B]

Right.

[A]

And 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.

[B]

That's the Paradise Lost, you know, Satan. Yeah.

[A]

What have I done?

[B]

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 in. I'm sorry, my art history is failing me. No, it's a specific reference, you know.

[A]

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 just feels very contemporary and funny. The movie is very, very funny and fun to watch, but it's funny in.

[B]

A really fucked up way.

[A]

Totally.

[B]

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.

[A]

Yeah. I think that 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.

[B]

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?

[A]

And the use of Lifestyles of the Rich and Famous and Robin Leach. In this movie, there is a scene.

[B]

That takes place quite literally outside Trump Tower.

[A]

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. 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 kind of. This is like the real Gilded age, where there's a. 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, and.

[B]

They'Re in this strip mall nearby.

[A]

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. This episode is presented by State Farm. You know what's even more impressive than being an expert at movie trivia? Being smart about saving money. And a great way to do that is by choosing to bundle home and auto insurance with State Farm. Talk to 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.

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[B]

Yeah.

[A]

Which is, I think, how a lot of people still feel 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. All 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.

[B]

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. Like, it doesn't. There isn'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 say the only moments where you, 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, 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 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 is, there's no attempt to like explain away the, the misdeeds and just like the grossness of the person.

[A]

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, they are the same as Jordan in that they are a product of their environment.

[B]

Yeah.

[A]

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, in their life and in the world. And he's, 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. 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, it's a. Where it stands like even in his entire career is kind of a fascinating conversation.

[B]

I mean, you and Adam Naaman and Chris did a Scorsese episode and it was, it was the one movie in all three top five.

[A]

Was it? I don't remember.

[B]

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 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.

[A]

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, 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. I mean, just completely misreading it, which is unfortunate, but I mean, it's an all time favorite of mine's movie.

[B]

It's not the movie's fault, you know. Well, I do think we live and we learn. Hopefully we grow.

[A]

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 the 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.

[B]

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. How money is evil. I don't. 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.

[A]

That stuff is unbelievable. I mean, that whole sequence is a wild, Buster Keaton esque, misremembered genius moment.

[B]

Let's talk about the Leo performance.

[A]

Let's do it. So you have written here that this is the single greatest performance in Leonardo DiCaprio's career.

[B]

It is.

[A]

I'd like to unpack that with you.

[B]

Okay.

[A]

Now, as much as this is our 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, 16, 17, 18.

[B]

This is like watching my son count right now.

[A]

One battle after another will be either his 19th or 20th feature film this century.

[B]

You can count to 20. Congratulations.

[A]

In fact, I counted to 20 in Spanish with my daughter last night.

[B]

And at her request, Nast gets thrown off at 14. You know, then things get dicey.

[A]

Yeah, Catorce. So we're not talking about one battle after another yet.

[B]

Yeah.

[A]

And I'm not. 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. 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.

[B]

Yeah.

[A]

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.

[B]

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?

[A]

I mean, PCA has been trying to get one battle off the ground for 10 years.

[B]

Sure. Once we. Once we get into 30.

[A]

Yeah, sure. Yeah. Well, the world changes. The world changes.

[B]

Sure. But I just, like. Let's look back. Even, like, our greatest filmmakers. Has anyone been like, yep, that was it.

[A]

I nailed that megalopolis.

[B]

Right. That's what.

[A]

Exactly. I think you're right that once you get past a certain timeline.

[B]

Sure. Guillermo del Toro has been trying to make Frankenstein for 30 years.

[A]

Well, sir, it's a very good topic of discussion for the Frankenstein episode, the Passion Project.

[B]

Top five. Anyway, Gangs of New York was never gonna be on our list.

[A]

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 got really got hip to Scorsese. And he made it his mission after Titanic to get Scorsese movies made. 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 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 and Juliet for a second, because I don't. 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. I will suggest Django Unchained as Calvin Candy, one of the great villains of the last 20 years, and he pulls no punches in that movie. He is as vicious and unsparing as I would argue any major movie star has ever been in a Hollywood Production. The things that he says and the things that he does. That was a really fucking brave move on his part.

[B]

And.

[A]

And it led to. I think. And you know, he had previously also just played J. Edgar 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.

[B]

Yeah.

[A]

Which is a great physical performance.

[B]

Who cares? So is this.

[A]

I agree.

[B]

He wore Bear, you know, whatever.

[A]

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 that Rick is his best performance.

[B]

Yeah. I mean, it has a couple virtuoso scenes. Obviously. The. What is the name of the TV show?

[A]

Bounty Law.

[B]

Like the Bounty Law scene where he starts crying. Yeah. You know, I get it.

[A]

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 Oliphant. Yeah. But him in the trailer breaking down, that's gonna be near the top of his reel at the end of his career.

[B]

But I would say that Quaaludes will and should also be at the top. It's at the top of my reel. Okay. You know, I had forgotten the dancing at the wedding.

[A]

I love that. I almost texted you about that too. You know, it's like again, dancing to a 60 year old blues song. It's so incongruous.

[B]

It's not like. It's not. You know, some people will pop out the moves all of 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 this?

[A]

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. And, you know, he's in the middle of a really interesting run of films where he's constantly playing this kind of comic drama, 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 Battle 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. So serious and a body of lies and revolutionary stationary road. Like, these are heavy movies. And he has really pivoted in this interesting way in his 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, 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 this guy's fucked up. Everything he's doing is wrong, but we don't want to just turn it off. Like.

[B]

Well, like. Like Henry Hill. He is also. The movie is about him, but he is our way into the movie. Like, he is the. 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. 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.

[A]

Sell me this pen you're referring to.

[B]

Yeah, sell me this pen. But there's like a queasiness and am I rooting for him? Like, am I like, is this a story? Is this.

[A]

Do we want him to be redeemed?

[B]

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

[A]

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 he. They're sort of having this very friendly but tense walkthrough 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 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.

[B]

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 such an incredible, amazing, messed up scene.

[A]

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 gonna 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 Belfort 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. Yeah, but it's not all roses. They're corrupt too. Or they. They also have this kind of like bottomless existential dread of, am I wasting my life if I'm not succeeding?

[B]

You know, what I had forgotten is when they. They do finally raid Stratton Oakmont, the needle drop is the Lemonheads. Mrs. Robinson, which I would also like to like.

[A]

How did that happen?

[B]

How. Yeah, how do Marty and Robbie Robinson become, like, aware of the lemon?

[A]

You know, there's like funky ones in this movie.

[B]

What's this process? But it's. I mean, it's just an absolutely, like, pitch perfect. A very funny, jarring needle drop. But even there, it's like, you know, everyone in their windbreakers and where it's just like, well, every. This is. This is all fucked. No one is.

[A]

Yeah. And I think if you wanted 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 Belfort 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?

[B]

Sure.

[A]

Catch me if you can.

[B]

I was surprised that you skipped over it when you were reading all the things. Cause it is really good.

[A]

And now I wanted to come back to it as like, to me, this is maybe the runner up to Wolf of Wall street because, well, it's very.

[B]

Similar, but just a lot more daddy issue. Christopher Walken stuff which pays off in the scenes with Tom Han, America's dad. But yeah, it's good. But this is. That's young Leo. I think that's like. That's of the generation of Titanic. And it is.

[A]

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. 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.

[B]

And sometimes you need to. But I just. I think it's like a very novel feat of this film that it doesn't.

[A]

And you know, Spielberg is obviously prone to daddy issues movies. So it happens. One other thing I. I wrote down here. This movie essentially breaks every rule. So I mentioned the into camera explanations and the voiceover.

[B]

Yeah.

[A]

Breaks the fourth wall and explains everything to you. It's an unreliable narrator, which is not that 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 Azoff. Jonah Hill was phenomenal in this movie. Super funny and pitch perfect in a lot of ways. Not a lot of nuance to these guys. They want something. They're hungry wolves.

[B]

I'm sorry, I'm just thinking about all the funny things Jonah Hill does in this movie. He's an incredible horse.

[A]

He's got the teeth, the way he styled his hair, the glasses, all of.

[B]

The running away from Bernthal and the strip mall. The cousin scene, you know, at the bar. It's. It's really good.

[A]

Steve, Steve Madden. They the, the casting across the board is really good also just for the.

[B]

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, is just very important.

[A]

Obviously it is true to the story of Jordan Belfor, but it is a perfect stand in perfect. And I will say as a 12 year old or whatever in living on Long island, going to the mall.

[B]

Yeah.

[A]

And trying to understand why every girl I knew needed to have Steve Madden shoes while looking at the shoes.

[B]

Yeah.

[A]

It didn't make sense.

[B]

Yeah.

[A]

But we did now. And now it does make sense.

[B]

We did.

[A]

You know. Does that make you feel any worse about the industry of, of fashion and style trends? That the people at the, at the Levers are, I don't know, monsters.

[B]

Just David Ellison owning all of Hollywood. Make you feel any worse about your DVD collection?

[A]

Yeah, it does.

[B]

Okay. All right.

[A]

Well it makes me feel worse about the future. I don't know about the past. He didn't do anything with the past.

[B]

Yeah, no, I mean I have larger concerns with the fashion industry.

[A]

Okay, what are they?

[B]

Well, you know how we're treating workers and obviously sustainability.

[A]

Okay.

[B]

And all of that stuff. Like where are all the Steve Madden shoes that I Wore in the 90s? They are not decomposing somewhere. They are definitely not made of natural materials.

[A]

Pairs of Steve Madden shoes did you own?

[B]

Well, so I had the loafers and I had them in like the 4 inch height and the 2 inch height and I.

[A]

Did you tower over all these poor young boys when you were like 13?

[B]

Of course. Like what, what's the alternative? And it's not my fault that wear flats. Yeah, you know, well, I had the 2 inch as well. But the, the chunky 4 inch loafer heel. If you, if Jack, Google this so that you can understand the reference. All right, we got a thumbs up.

[A]

Jack, don't Google it.

[B]

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, you wear them out.

[A]

Wear and tear. Yeah, sure.

[B]

And it's not exactly like they're made for a lifetime, except for when it comes to landfills.

[A]

Well, Steve Madden, thanks 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.

[B]

What would you, you want Silence. You know, I was never Going to do silence.

[A]

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. Regular paying crowd by myself on Christmas Eve. And in the morning, it was the movie event of the year for me.

[B]

No, I think I saw it at the arclight by myself. I would have said it was the week before Christmas, but now that I'm thinking about it, maybe it's Christmas.

[A]

Maybe it was the week before. It might have been the week before.

[B]

Cause 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, like, okay, boys, it was December.

[A]

23, 2016 is when it opened.

[B]

Okay. So it must have been like that after Christmas vibe I saw.

[A]

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.

[B]

Okay.

[A]

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 also would have been worthy of exploration.

[B]

I would have looked into it.

[A]

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.

[B]

That's not their list. It's our list.

[A]

Are you saying you're never wrong?

[B]

When I am wrong, I say I was wr. But it is pretty rare, you know.

[A]

You'Ve made yourself so lovable.

[B]

Yeah.

[A]

Recommended if you like.

[B]

Yeah.

[A]

Did you make. Did you write these down?

[B]

I did, yeah.

[A]

This is funny, right? Because you. I like what you written down here. Boiler Room, Margin Call.

[B]

In 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.

[A]

Yeah.

[B]

Then this is the ultimate. This is, you know, the mothership.

[A]

Yeah. Well, I think also Wall Street, Oliver Stone's film is also probably a part of this lineage of these kinds of movies and stuff.

[B]

Gordon Gekko gets a name check in.

[A]

Wolf of Wall Street. He does. That movie feels very small compared to Wolf of Wall street, you know, it is a big movie, but also the.

[B]

Second half of it is kind of like, what's going on.

[A]

There's stuff in it that it's not my favorite, as we've. 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.

[B]

We also didn't really talk about this movie came out in 2013, which is pretty soon after the 2008 crash. And definitely at the time felt like an. If not a response to then like in conversation, like yet another piece of like, oh, this is what they're up to on Wall Street. Yeah.

[A]

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.

[B]

But then 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.

[A]

They're really twinned in a lot of ways. You could argue that. I like the Big Short. The worm turned on Adam McKay for a variety of reasons, but I still think that those couple of first few socio political 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 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 out. And then you've listened one battle after another and you know, we're 24 hours out from the movie event of the year.

[B]

I know. I'm very excited.

[A]

I am too.

[B]

You're a little nervous. You're feeling the pressure.

[A]

I want to do a good job on our episode.

[B]

Yeah, I do. I do as well.

[A]

This very rarely happens. The last time this happened was Once Upon a Time in Hollywood.

[B]

Okay.

[A]

Where I was like, I've been waiting for this all my life.

[B]

Yeah.

[A]

I've been waiting for somebody whose work I care about this much, who I know has made, done something special. 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 that's like the best feeling in the world. There have been 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.

[B]

I'm psyched. I can't wait. It's an Amanda movie. We'll just move on to it. It's an Amanda movie.

[A]

And that'll be. Is it next week? It's next week, right?

[B]

I don't know, Jack.

[A]

October 1st.

[B]

Okay.

[A]

It's next week. Okay, we'll see then.