The Big Picture - The 25 Best Movies of the Century: No. 3 - '25th Hour’

Episode Date: November 26, 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 Spike Lee’s ‘25th Hour,’ one of the most present tense films ever made. They discuss its fascinating legacy as a somewhat under-discussed masterpiece, explain why Lee’s stylistic choices are deeply moving, and identify the impressive fricative tension in all of the movie’s ideas. Hosts: Sean Fennessey and Amanda Dobbins Producer: Jack Sanders Shopping. Streaming. Celebrating. It’s on Prime. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I'm Sean Fennacy. This is 25 for 25. A Big Picture special conversation show about 25th hour. And this life came so close to never happening. Amanda. Yes. I believe that this is the mystery movie on our list. It is.

This is the movie that I have seen vanishingly few people, figure out what would be on our list, which I find interesting for a variety of reasons. Now, this movie is of course directed by Spike Lee. It is written by David Benioff, based on his novel. It stars Edward Norton, Philips Seymour Hoffman, Barry Pepper, Rosario Dawson,

and a Pac-win, Brian Cox, a number of Spike Lee All-Star character actors, shot by Rodrigo Preeto, music by Terrence Blanchard. And if you've been listening to this show, you know that it's coming. Or you should. But this is a big movie.

It's a big movie for me and a movie that I know you've always loved, too. So it has been interesting that people have struggled to identify, one, that we would do a Spike movie. Because we both love Spike. Right. And two, that this would be one of the movies. But for whatever reason, on social media. It's true. Even among friends, people have just not known what would have been in our top three.

Our good friend, Dan Riley, has been trying to guess for two weeks now because we had been talking about there's one surprise left. There's one thing that you won't see coming. And that we were very excited about. And Dan has been trying to guess for weeks, and he's just, like, not even close. And I told him. I was like, you can keep texting me. And I will keep saying no. But he didn't get there.

But we've talked about it many times before on the podcast. And even this year, there have been clues when Spike Lee came on this podcast. He identified 25th hour. And I was like, oh, no, is everyone going to guess now? And I reacted so excitedly when he said 25th hour. And then I drafted it in the New York City movie draft. and, like, you know, with a shot straight to the heart at Chris Ryan, because this is also one of his favorite movies. So it was a no-brainer to both of us when we were making the list.

And I put together a long list. You did a ranking. And let's talk about it now. This film was originally number two on our list. It was. And yesterday, you had a crisis of confidence. I did. And you presented to me the case for switching number two and number three.

And I said, okay, I said I understand it. I think that in my own world, this would still be at number two instead of number three. But we can even, we'll talk a bit about that when we get to number two, which is also just out and out masterpieces. It's only masterpieces from this point out. I would argue it's probably 25 masterpieces on the list. Yeah, that was kind of the idea. But it was never a question that it would be top five. And we didn't even talk about it.

You just slotted it at number two, and I was like, yes, perfect. We never strategized around this. Yeah. So why are you, like, some of it is just that that's how we work and it's unspoken and we're like, great, okay, we don't need to talk about this. But have you thought about that? Like, what's your theory about why it is that high, like in this list of films that we have? Well, there's a variety of reasons. I mean, I think that that probably goes toward explaining why we chose it in the first place, too.

This is probably revealing some the direction of where we're headed on the list. but I think most fans of the show and for regular listeners will know where we're headed here. And I see this very much as like a story of America in three parts and that this movie is kind of when we were coming of age

and right around the time when we were moving to New York, this was the story of the present. This is one of the most present tense films ever made. And the reason for that is obvious. This is a story about a guy named Monty Brogan who's a New York City drug dealer, a guy who's from Brooklyn,

who gets... arrested and is sentenced to seven years in prison, and the 25 hours that we see in the film is the final day before he goes to prison. And this film was made, was in development and then in production during and in the aftermath of the attacks on 9-11. And so this is like, there's not really a lot of kind of big scale, corporately distributed works of art that are about this moment in history. And, like, for me, I was in college at this time. I shortly moved to New York thereafter. Same for you. It's a senior in high school, yeah. It's a 9-11, of course, a world-changing event for anyone in America, but as someone who was born and raised in New York, whose entire

family lived in New York, was, you know, earth-shaking in so many ways. And also, Spike Lee, just an insanely influential and inspiring person to me, like an artist who I just really have always been interested in since I first saw whatever that link in. the chain of movies was from Do the Right Thing, Jungle Fever, Malcolm X, Mo Better Blues, Crooklyn. Like, I saw all those movies kind of in quick succession as a teenager and have just been locked into his world. So this movie, to me, is like a major, major convergence.

And it isn't on the New York Times list, you know, it isn't. And so it exists in this kind of space where, like, if you bring it up to people who've seen it, they're like, oh, I love that movie. Yeah. But maybe not ever, maybe it has not been distributed in quite the same way. when you mentioned the Spike thing when he was on the show, and he pointed that out as like a movie that he thinks is still a little undiscovered

out of his filmography. But then I talked to Noah Baumbach on the show last week, and I asked him the same question that I asked Spike, and he was like, well, what did Spike say? And I said, 25th hour. And he was like, 25th hour. That's like, everybody loves that movie, you know? Like, he didn't think that that was,

that didn't even make sense. Yeah, it's, I guess it's an unspoken masterpiece story, not even forgotten, but kind of ignored, I guess. or just you have to jog people's memory about it. And I don't know if that's because of the 9-11 of it all. Meaning people don't want to spend time thinking about that? Yeah.

And also because it's, as you said, it's very present moment. So when we think about 9-11 now, we contextualize it, we politicize it, or we put it in the arc of American history as we understand it, or we make a joke out of it at this point, which is not respectful at all, but is how we deal with... Blank was my 9-11 or whatever. Exactly. And, you know, it was like memeified, this tragic event.

The death of irony of 9-11, and then the... And then it resurged and became even more messed up. So this film isolates the feelings of uncertainty and anger and fear and total discombobulation that we had in that moment. And it's just not what you say. summon when you bring back that time period, or at least not what I do because I repress all things. But I think we as Americans definitely repress, and this is a movie about a lot of Irish guys

who can't talk about their feelings. So they're repressing, too. And then I do think also this came out in 2002, and after 9-11, Hollywood and movies and culture and what we valued as like good or important or how we were processing things or even the types of films we wanted to see like really changed. And so I think it just got lost a bit in the shuffle of a reinvention of our understanding of like Hollywood American output in the early 2000s. I think that's right on the money. This is also the time of Sam Ramee's Spider-Man movies, which were also in New York set movies about heroism. And that there was something, I think,

think part of that movie's success, obviously, it's a Spider-Man film. People love Spider-Man, but there was something uplifting about watching Toby McGuire who produced this movie and who was the one who located the David Benioff book and eventually got the ball rolling on the whole film. Those films popped in part because we were looking for something a little bit more hopeful in the aftermath of this event. This is a movie that very much leans into the specifics of the event. It's not a movie about 9-11, and it is a movie surrounded by 9-11, and because it is so present tense, and because it is a tough movie with no simple answers that is basically defined by as deeply flawed characters, you could make

the case that every character in this movie is kind of a creep or a loser or somebody with maybe the exception of Naturalel, that there's the kind of note, it's like a loss of innocence movie in a lot of ways, and 9-11, for a generation of people, is a real loss of innocence moment. And so it's just a hard movie. And there are funny things about it. It is amusing. You know, anyone ever tell you you look like an optical illusion? You know, like there's stuff in the movie that it's, it has a great energy and vitality to it. And it does have a sense of humor. But it's, it's quite sad. No, I mean, it's brutal. It has two of the great scenes of the 21st century, in my opinion, as well. And, and I mean that both emotionally,

but just like actual filmmaking, the writing, and then the way that Lee adapts it, and his, like, his particular style put to the subject of New York in the, like, the fucky rant, and then the ending, which is, like, some of the reason that this movie is on the list for me is just technically speaking, it is an out-and-out masterpiece. It is the best ending of a movie in the 21st century. I put that question in the doc. Straight up. I think that there are some contenders.

I think it is over, it is, I consistently cry at the end of the movie. Yeah. And there's not a lot of movies that, like, I can see it on eighth time and still feel very moved by. I cry at something different every single time. Yeah, yeah, yeah, yeah. It's funny, there's definitely, this is going to be one of the lesser scene movies, I think, in the top 10. And there are probably people listening to the episode who have not seen this movie. I highly encourage you to see it.

We're going to talk about all the details of it throughout this conversation. I do want to go back to Lee because. he, I wrote down that this is his last out-and-out masterpiece. I think he's made very good films. I think if we were talking about what is this standing in for, the next best contender for the 21st century for him would probably be Inside Man, a movie we both love, which is just an absolute corker, like a really entertaining thriller, a good New York movie, you know, world-class Denzel performance, totally.

And I think that, I think this is where we reveal that we don't have a Denzel film on our list. I hadn't even thought about that. Yeah. We talked about it a bit in terms of. at the disselection committee, but yeah. Right, okay. Yeah, so there's no Denzel. And that's a movie I really like.

That movie feels a little bit more thematically thin. It's just, like, to me, it's a really good genre movie. Yeah. And it has some ideas in it, but this movie is, like, overloaded with ideas. And as I watched it again last night, it was just making notes. It was becoming more revealed to me, all the things that it makes me feel and try to understand. But for Spike, like you said, that style that he brings to every film where he's got

these six or seven moves that he makes in movies. And sometimes when they're in his world, it can feel a bit like a closed loop. I find it in his 21st century movies sometimes, it feels a little iterative where I'm like, especially with movies he's written, I'm like, I kind of know why you're putting this character in this position, and when you're doing the double dolly and what the character's mind state is,

this movie, because it's based on this Benioff book, because it's in a similar world to what you would see in his films, but the register is a little bit more somber. I think his stylistic moves are more surprising and even more emotionally moving. It reminds me a little bit of like seeing Malcolm X for the first time where you're like, oh, he's using all of the stuff he's figured out

to tell this big story. Right. But in this case, he's kind of shrunk it down to this really tight character piece. Yeah, and it is, I always think of the John David Washington anecdote from making Black Klansman. Wait, he just kept asking Spike Lee,

like, when's the double? Dolly shot, one's the double dolly shot. And you do. There is that moment you, you know, grow up, you get used to watching his films and you are expecting them. But as you mentioned, when he's, when he's meeting some other material. And this is like a true work of adaptation because this novel was written before 9-11. And so the way, and it's set in New York, but what Spike Lee is doing in the moment to make this a film about New York and America in that. specific time is additive, right? And he's finding different. And so it's a, it, it is truly like when two great minds and two great skill sets, like meet and elevate the other. And so it doesn't, you are excited to see who gets the double dolly shot. And it also, you know, conveys like a significance about, oh, okay, now I'm like supposed to pay attention. I know this is a, you're saying something to me. But because it's not just a combination. of all of those moves

that he's working through some other stuff and from some other sources it's really, really exciting. It's really powerful. I think you can also feel a lot of actors in this movie who really want to be working with Spike

Edward Norton, who is the star of the movie. Let's spend some time talking about him. So he is in 2002 at the absolute center of Hollywood. Yeah. He's 32 years old. He's already had two acting Academy Award nominations. He has gone from wonder kin, where did this guy come from in primal fear in 1996,

to headlining four films that year. In 2002, he was the star of Death to Smoochie, Frida, Red Dragon, and 25th Hour. He was also dating Salmaheach at the time. Right. He'd been trying to get, he basically had been saying to Spike for seven years, let's do something. I really, really want to do something. So, you know, I think originally Toby McGuire thought he might play this part.

he had a conflict with Spider-Man and it eventually became an editor-in-norton movie and I've said this before I probably said it on the primal fear rewatchables podcast but I was like this was my guy this was my favorite actor

like this was the person who when I was 15 and really getting into movies it was like this guy showed up in a Milo Schormann film he was like showing up in Spike Lee movies he was doing American History X he seemed really brave and audacious and really interested in transforming

in every part. I was really into him. His career has been a little funny in the last 20 years. He really has more... He's had leading roles but really hasn't been a leading man

since this period of time. Sure. So I see this very much as like a time capsule but it's also an amazing representation of what kind of actor he is and not in the ways that he was exercising before this.

So in the past, he would be very big. He would do accents, he would have big speeches, He would raise his voice and get angry or he would be twitchy or something. Monty Brogan is more like a, he's like a Brando or like a Pacino character. Yeah. You know, he's a 70s tragic loser.

He is, but he has even, like, tamped down the charisma. You know, there's something, and the anger. Like, this is a really angry movie. But in the most famously angry scene, there it's, it's, it's. done through a mirror. And it's not even the actual, it's, I mean, it is Edward Norton as Monty performing it, but it's his reflection in a mirror that takes over and starts yelling all of these things because the actual character can't access any of it. That's what it is. Yeah. It's an internal monologue that is made external. He's, Monty goes to the bathroom while

he's having one last drink with his dad before he goes to prison. Yeah. And in that moment, he gives this, fuck you monologue, which is in the novel. Right. Even though. The novel predates 9-11. It is still very much about the way that a lot of New Yorkers are, which is that they are constantly aware of who is around them and making their life more difficult. And sometimes that comes out in aggression, but ultimately it speaks to, like, self-loathing or self-fustration

or self-pitying. But also, this is, that segment is a love letter to New York also. In, like, it is filled with, like, hate speech. And it's very ugly and relies on stereotypes and is also written in a way that observes and understands how New York works. Yes, it's very true. Because it is, and listen, you have to be angry to live in New York and you have to kind of. Yeah, you have to put your hood up and just like get through because it's crowded and

everybody's going to be like throwing their elbow, trying to make their own thing. But it's written from such like a knowingness and observable. that only comes from like truly understanding the place. But even that, it's like, it is separated from the character. And so the rest, Monty is like, he's not seething, like, Pacino. He's not, there's no last, like, fight left in him. Like, there is in Brand, like, there usually is in Brando. Yeah.

It's just, he's, it's, it's resignation. It's a movie of regret in so many ways, because this is a guy who was obviously very smart. He gets into this private school on a scholarship, even though he's, He comes from seemingly a lower middle class background, and he fucks up because he starts stealing drugs in school. He gets kicked out of school, and then he becomes a career drug dealer. And he gets a little greedy, and he gets pinched, and that's when his life starts to unravel

a bit. Using a single person's moment of inexplicable sadness and frustration and the sense of the feeling of my life is over. It's done. Which is exactly how everybody felt in New York for a period of time. Yeah. And you can say it's happenstance or great artistry making that connection, or you can say it's an act of critical fusion that some of us who think hard about movies

brought all of these things together. Yeah, it's textual. It totally makes you go back to the very specific place. Like I remember my feelings at the time as a fucking 19-year-old who didn't know anything, who didn't understand the global context, didn't know what Al-Qaeda was, we didn't, but just there was a very specific combination of rage, sadness, what I would describe as like a weird bloodlust that found its way into the culture. Yeah, absolutely.

I mean, I just vividly remember sitting, you know, I still lived in Atlanta, but we just like sat there watching the news and just like watching live footage of, of bombs that the United States was dropping on places that were not the United States and some sort of, like, I don't even remember where, which is one of many parts of the problem. Totally. And those actions felt like manifestations of the same feelings that people were having on September 12th, you know, which were obviously completely wrong and misguided and awful and obviously continued a terrible cycle. But this movie, like really within these characters, I think, completely manifest all of those feelings that people were having.

And at no greater moment, I think, than in the fuck you rant that he gets. Right. Well, but there's also, it literalizes that there is a scene filmed above Ground Zero. And it's where Barry Pepper's character, Francis, Xavier, I can't remember his last name. Slattery. Slattery, Frank, lives. And the Phillips Seymour Hoffman character comes to meet him and they like sit in the window quite literally looking over Ground Zero and the cleanup site. And they have a conversation about how the air is bad down there and, you know, fuck the time.

I read the New York Post, just like iconic Barry Pepper stuff. What happened to Barry Pepper? He's so, I don't know. I googled that last night. He's so good in this movie. Yeah. And then the conversation turns to Monty. And it goes from 9-11 to Monty's like impending prison sentence and how they as friends

are going to deal with it. And I had forgotten this, but the very last line after Frank is like, we'll never see him again. It's over. He says, it's over after tonight, Jake. Wake the fuck up. And then the camera pans up from them to the ground zero cleaning site and you watch the trucks moving through sweeping up with like the Terrence Blanchard score is unreal. But at that moment is like really going for it. Totally appropriate for the big swells that he has known for.

But and I was just like, oh, so it's literally it's over afternoon. This is quite literally about America in this moment. And I'm watching what the camera wants me to watch and thinking about it. Yeah, there's so many things that are, it's like a mixed media quality to a lot of this, too. Because like one of the things that Monty mentions in his Fuck You monologue is Enron executives. Yeah. And the idea of like the way that corporate power kind of led us to this place, there's obviously no greater representation of corporate power in New York City than the Twin Towers and the idea of trying to smash that and that being under attack. But then also this kind of divergent feeling, this oppositional feeling of corporate power also attacking regular people, like regular middle class people living in New York City and the encroachment that they all feel in their lives.

This movie has like a really affrictive tension in all of its ideas. Like it's just not a clean and simple movie. You mentioned that Frank in that scene says like, it's over. Monty's never coming back. You're never going to see him. And Jacob, Philip Seymour Hoffman's character, will not accept that. But then later in the film, we see a long conversation between Frank and Monty. And Frank is insisting, like, you're going to survive, you're going to make it.

I'm going to be there for you when you get out. We'll start something together, yes. Which is just, like, heartbreaking, you know? And he's like, is he lying to himself? Has he convinced himself over that night? Is this just something that friends do for each other? Right. The truth is kind of all in the middle there somewhere.

But I've been saying to you the last day or so, like, this is really a movie about how men are with each other. Sure. And how they, like, kind of don't know how to tell the truth to each other sometimes. and they feel that they need to support each other but also break each other's balls at the same time and there's got to be one guy who's like I'm the truth teller in the group and there's going to be one guy who's like I'm the empathetic guy

but then like people's personalities merge and they split apart and as I was watching the movie very closely I was like ah that I think the Benioff idea of the movie is that these three friends that Jacob and Frank and Monty are kind of like they're kind of the male

psyche. They're the ego and the super ego and the id You know, Monty is the ego, Frank is the super ego, or, no, Jacob is the super ego and Frank is the id. Like, when you put them all together, they seem like a person. Right. But individually, they have all of these trademarks where, like, they're kind of bouncing off of each other throughout this movie, which is also a clever idea about what happens to friends you have in high school, right? Where you're like, you could never be closer to somebody than when you're 16 and then cut to 10 years later and you're like, why was I friends with this person? What did we see in each other?

I think that I spend like a moderate amount of time thinking about the male psyche when watching this movie. Like I'm not really breaking it down into parts, which is also possibly just how much time I devote to it in general. Yeah, but you're confronted by it on a regular basis. Right. And so, and this is a very familiar version and a very perceptive version of what I am confronted with, with a bunch of guys who are connected and sort of devoted to each other, but it's very complicated, and they just, like, can't figure it out. We were talking about... What percentile do you think I would be in in the Bachelor scale if I were single?

Don't answer that. Let's see. Money and... What's the other thing Jacob fails on? Bad breath. Bad breath. Yeah. I can't really speak to that.

Okay. Thanks. You don't really eat any food with, like, flavor. I drink a lot of coffee. That's true, but it doesn't make it this far. Fortunately, for everyone involved, I've been married for. for some time. But I was thinking last night about our conversation around the movie Friendship, the 2025,

which was another, I thought, perceptive and rare movie about how men don't know how to talk to each other or be friends or how complicated it is. And we're very familiar with the women genre of that. Yes. But this is definitely the same type of movie. It is. It's hard to exist as a person in the world or a man in the world. and it's also hard to know how to talk to each other.

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Last minute holiday magic, it's on Prime. Head to Amazon.com slash Prime to shop now. I think there's some struggles of expression and you have this moment late in the movie where Monty wants to get beaten up so that he goes into prison looking less pretty than he than Edward Norton is. And, you know, that whole scene

where they're beating the shit out of each other is this conclusive moment of like, this is how men feel sometimes, you know? Like they want to just bash each other's heads in. I think that there is a lot of other, like, really rich stuff inside of the movie. The Monty getting arrested and the kind of sting and the idea of who has ratted on him is a strong narrative through line. And so for some of the film, he feels that Natarelle, his girlfriend, played by Rosario Dawson in the movie, may have been the woman, the person who told the cops that he was hiding money and drugs in his couch cushion. it's possible that it's maybe someone in the criminal organization that he works for, the Russian mobsters that he's working for.

So in that process of him getting arrested and being questioned by police officers, you get what feels like really classic Spike Lee material where you've got, you know, clay from the wire before the wire doing she. Yeah. And in the conversations that he's having with Monty, they're full of very specific, explanatory language about mandatory minimums, the Rockefeller laws, the kind of like late-stage capitalism of the war on drugs, you know, that in the early 2000s, I say this as somebody who was raised by somebody who was working in this space. You know, this was kind of a pre-fentanol, like, rise of heroin moment, I would say, in the drug trade.

And it was still kind of like a high-class, low-class situation. There's some very savvy stuff about the Simon character, who's the first character we see in the movie approaching Monty sitting on the park bench, who's an addict who looks really run down. And then in a flashback sequence we see much earlier in the movie. He's a businessman wearing a suit buying from Monty. And kind of just the way that this world, what Monty is doing is evil and soulless. And also the way that people who become incarcerated or treated is also extremely dark.

and in some cases, corrupt. And the film is trying to leave the nuance up to you. It's like nobody thinks that the cops in this movie are the good guys, even though we know Monty is a piece of shit. And literally his best friends say he's a piece of shit, and yet we still feel affection for him. He's not just, like, immoral, you know, and a bad guy, but he also fucked up.

Like, he got caught. He wasn't even good at being a bad guy. He just totally screwed up. and for what? Yeah. I think that that is, I would say that this is the most 70s movie that we have on our 21st century list.

Yeah, I guess so. I mean, definitely the whole statutory relationship aspect of it. We can discuss that if you'd like. There's definitely something, in addition to the male friendship quality. Yeah. I think this is a movie that's pretty tough on the perils of masculinity in general.

You know, if you look at the fact that Natarelle is seduced when she is 17 years old on a playground wearing a Catholic schoolgirls uniform? Yeah. And then later in the film, obviously, Jacob's student, who's played by Ada Pac-Wind, who is also 17, and lord into a club.

Hold on, I got to add, this movie is standing in for... Okay. There's another one. Putting it down. You know, it's not an accident that there's two different examples of men cruising for underage women in New York City in this movie and not really

letting them off the hook. And they've cast actors in Hoffman and Norton who are like inherently sympathetic. You know, when you see them in a movie, you're like, I hope that person's okay. They're creeps. You know, it's a movie about the creepiness of dudes as well, among a million

other ideas. As always an incredible Hoffman performance, the scene in the teacher's lounge just absolutely brutal. And then when they're... The one when she comes in to ask why did I get to be? Yeah. And did... He is not doing anything and is also completely turned on and freaked out and panicking all at once.

Yes. While so very still. And then I just also, the physical acting of in the club when he's just like this with his hands over his face for a while. He's the embodiment of shame. He doesn't, he didn't get late enough when he was a teenager and now doesn't know how to relate to women and is identified as like a, you know, rich kid trust fund. guy and has no experience in the world beyond the world of ideas that he likes to teach. And so he's totally arrested. He's, like, arrested in his development as a person. I mean, there's... He's not actually arrested in the course of a film. No, other people are arrested in the film.

It's like not, outlook not good for him. He might make some mistakes. Well, no, when he's just begging her, could you like, please not talk about this at school? I mean, you're going to get fired, sir. There is literally an R. Kelly joke in the club scene. And this is, obviously there were many rumors and maybe even the tape had been circulating at this time of R. Kelly's heinous acts.

But this is before Ignition Remix even came out. Like, this was in the culture and this movie is putting that stuff into the culture again and kind of making us confront it. And then the other thing, too, about Monty being kind of soulless is Monty wants money so that he can feel safe and have power. And that is also kind of an inherent characteristic of New York. there is a status seeking quality about New York City,

at least that I felt when I lived there. Yeah, of course. Where it was sort of like, what are you wearing? Where are you going to that club tonight? You know, what street do you live on? Well, I mean, what do you do? And what does that say about your level in the world and how much money you have?

Yes. And even when we see the Anna Paclin character come and, like, enter the club with these guys. Yeah. She's like, is your friend, like, famous? Or what is he? because he has like all these connections and power and talking to the Patrice O'Neill character at the club door.

And it's pretty savvy about that too, you know, that I did go to clubs in my 20s in New York. It was really fun. It did feel exciting. It was, like, it felt special, you know, and seductive. You can get kind of really trapped inside of that world very quickly and it can ruin your life pretty quickly as well.

There's also the introductory scene we get for Frank is on the trading floor anticipating unemployment numbers and how they will affect, you know, inflation and wage and investments and everything. And then people cheering when the, you know, at an unemployment number and what it means for their moneymaking, it's if you want to talk about like soulless commodification of actual people, it is exemplified.

And then his boss is like really mad at him for, you know, taking some bet, like you need to come out with us tonight. It's all right there in one scene. Yeah, Al Palagonia, who is one of Spike's best friends and who often does literally sit courtside with Spike, and is so funny in that movie as Frank's boss. And there's a number of other very familiar people. I mentioned, you know, Clay from the Wire, Isaiah Whitlock Jr.

And Michael Gine, who's been in a couple of his films. And you've got, like, also very memorable people in very small roles. Like Aaron Stanford shows up very quickly as one of Frank's colleagues. Vanessa Furlito is a... Rosario Dawson's friend. Are you familiar with Tony Siragusa, the guy who plays Nikolide, or Kostia, rather? Only from 25th hour. So that's the only way you've seen.

Do you know anything about him? No. Should I? Do I? Well, I'll tell you who he is. He was a defensive tackle for the Colts and the Ravens for 10 years in the NFL. He won a Super Bowl with the Baltimore Ravens. That makes sense based on his shape.

He is not Russian and was born in New Jersey. Okay. Well, he clarifies that he's Ukrainian. Sorry, Ukrainian. Would you have guessed that? No, but now that you say it, you know, he does look like a cartoon of a football player that's in like the 1970s book about New York that we read our children just like from a triangular shape. He was a talented and useful player and he played on arguably the most fearsome defense in the history of the NFL. He just passed away a few years ago.

I didn't realize that. His casting in this was like somewhat lamploid. It's a pretty bold stroke in a movie that is very naturalistic. I think it actually works. I know some people would disagree. They would say, like, this is a flaw of this movie, the idea of putting Sir Rousse in it. But like the idea, like a non-professional actor who's in the middle of his NFL career just showing up in this movie as a Ukrainian gangster is just though another wild, like, Spike Lee stroke. Anyway, I just thought it was notable.

I learned about it just now, and I think this is an excellent film, so I don't have a problem with it. The movie is also just very personally resonant for me. It's about Irish guys who spend a lot of their time in bars talking around how they feel using sports as like a entry point into their relationship with their parents or their friends. You know, the conversation between Frank and Monty later in the film when they're like, we're two Irish kids from Brooklyn, how can we not have a bar?

You know, Frank saying, I'm Irish, I can't get drunk. I know exactly what I'm saying. There's just like a tonality to the way that these. guys talk, that just feels very familiar to me. That feels like, like, when you're watching fried green tomatoes and you're like, this is exactly what my life was like, you know? I mean, this does fit it, as do all Spike Lee movies, are of like foundation for my understanding of New York. And I think, you know, I mostly talk about how I moved to New York because of Nora Ephron movies, but I had seen more Spike Lee-based New York movies than

Nora Ephron movies. There are more. Exactly. And I had seen all of them. And I am very, very hard on my high school in many ways, but they did show us do the right thing in high school. Wow. Pretty good. So to me, it's familiar in like my understanding of, of what New York is and how New York people talk to each other. And, you know, it's funny. Like, when I talk to your dad, I definitely am reminded of these scenes, but it's like, you know, he's familiar to me from 25th hour instead of 25th hour instead of 25th hour being familiar to me because of your dad. Yes. But they are, it's, you know, it's a cortex. Yeah, I think I'm very struck by the conversations between Brian Cox and Edward Norton in the movie. And I would say my dad has a little bit less of the melancholy that Cox's character has because

like he's kind of dealing with grief and he's lost his wife and that kind of shattered his world and he's a recovering alcoholic and but there's just something in their relationship which is like sincere and close but there's something strained about it. There's something that can't be said and Monty is at this breaking point in his life and he's almost trying to say to his dad in the film like, this is how it really is like your optimism is sweet but it's useless right now

and then that gets flipped on its head at the end of the film and you mention the ending so you know at the ending of the movie Frank's or excuse me Monty's been beaten up by Frank on purpose yeah and his dad picks him up and he's ready to take him to Otisville up to prison

and they get in the car and on their drive Brian Cox just kind of starts to lean into what could be, which is what if, instead of stopping at Otisville, and I love how he's like describing the details of the directions, like, we'll take the Springbrook Parkway, which is like such a New York thing. And even the springboard into the, you know, the imagined sequences, like I could just take a right here and we'll take the George Washington Bridge West. Yes. You know, get you stitched up and keep going. Right. You've never been west of Philadelphia,

have you. And he's, the, the movie starts showing us what could be. And what we want to You know, we really want Monty, despite everything he's done, having spent this whole day with him, we want him to break free, you know, to not have to go to prison, to not have to confront this terrible thing. And I don't know if I can really think of another sequence like this in Spike's career that looks and feels like this. Like dreamlike but real. Yeah. You know, like the color palette is kind of washed. And it's set up throughout the film. there are flashbacks where we learn about how Monty's got into this situation,

but they're introduced as happening at the same time. They're not shot like in a different film stock or, you know, there is, it takes you and it to realize, oh, like, I'm watching something that happens before. Yes, the first flashback, like, wrong foots you. Yes. They get out of the bath to answer the door. Exactly. And so.

That's a slick filmmaking move, by the way. Yes, and exactly. But so it then makes sense. you up so that you're watching and you're like, oh, did they turn? Like, is this happening? And you know it's not. It becomes like a little bit hazier and the Brian Cox is just is narrating it in sort of like the subjunctive tense. But it's the longing and also the knowing in the moment that this actually is not happening, but you want it to so badly or you're so afraid of what is happening. instead, is, it's astonishing. I've never experienced anything like it in a movie. There's a ton of setups and a ton of individual small moments we see about what his life could be

done in this very quick montage. I mean, it is less than 10 minutes and photographed so beautifully. The whole movie is photographed so beautifully, you know. The bus shot. Yes, when the bus moves away and they're standing there. I mean, it's, yeah. It's honestly, it's incredible. I think this is like a full-blown out-out masterpiece. And I think a lot of people do agree, but it just does not have the same reputation as a lot of the movies that we've talked about that people are calling for. How could you not include this? How could you not include that? I was thinking about Prieto. I don't even know how Prieto got on this movie. I assume maybe because he shot Frida for Salma Hayek. And obviously, Norton was involved

in that film. Yeah. And so in two, so Prieto, you know, made his name on Moris Peros with Diener E2 in 2000. And then he starts getting hired for Hollywood films. He shoots this movie Original Sin with Angelina Jolie and Antonio Banderas. And then in 2002, he makes Frida 8 Mile on 25th hour. And then 21 grams, and then Alexander with Oliver Stone. And then he shoots Brokeback Mountain. And he's, you know, off to the races.

And then he becomes a corsese cinematographer. And he's like, he's one of the great living cinematographer, who's not one of an Academy Award. I think we talked about him a little bit during the Wolf of Wall Street episode. He is a genius. He is an amazing filmmaker. And he's still pretty young at this time. He's had plenty of experience in Mexico, but certainly in Hollywood films. And him colliding with Spike, and I don't think that they ever worked together again, has also, I think, brings something special out of Spike.

So with Spike, you've got Barry Alexander Brown cutting the movie. He cuts all of Spike's movies. You've got Terrence Blanchard, as you said, doing the score. Those are familiar voices. But adding Benny Off and adding Prieto, I just feel like lifts this movie. above some of his other work because it just gives it a different texture, a different sensibility, and makes it feel special. All the, the club scene, but especially the scene of Frank and Monty, are they like in a

bat? What is the overlooking, the blue room? You know, and it's just all shot in that. It looks like a private party room, yeah, above the club. But at some point, like, you forget that it's just completely blue, but it looks so beautiful. And all the lights there. And, I mean, the montage, and I'd forgotten one part of the ending is before Brian Cox starts the, you know, imagination, they're just driving through New York and you see all of the people in, like, in one shot from the fuck you montage.

Or not all of them, but many of them. And they're all smiling. And then the little boy in the bus who writes his name. I mean, it's just. It's beautiful. It's gorgeous. it's incredible a couple of other things about this

so one thing about the blue room you know the other room in kind of parallel action during that sequence is Jacob and Mary in the red room yeah and you know there is the real like the heavenly safe space Frank and Monty moments before

you know they're forced to plunge below where Jacob is where he is making a huge mistake and basically banishing himself to hell yeah not that subtle but still looks beautiful. Colors are good. We don't use them enough. Of course, they're essential.

We talked about them when we talked about Mahal and Drive, too. So what's the film's legacy? So, A.O. Scott and the Times gave this a rave. Roger Ebert gave it three and a half stars. He overtly compared Monty to Enron in his review and said that

this guy, no matter whatever we feel for Monty, he is just as bad. And he is a representative also of, like, the way that corporate America has kind of violated our trust. This movie is number 26 on the 2016-21st century BBC poll. It was number 24 on the Rolling Stone 21st century poll. And it didn't make the New York Times list, as I mentioned,

and no Spike Lee movies made the New York Times list. Well, this would be it, right? I mean, I think so. I love Inside Man. Everything else is 20th century. Well, you know, this is kind of difficult to I don't think you couldn't do this because it was a four-parter

but I think when the levees broke the Hurricane Katrina documentary that he made for HBO which is like also a major accomplishment a huge work of his I guess it's considered a television miniseries and not a film. We also didn't do documentaries on this list. We didn't, but I meant for the Times.

The Times definitely has documentaries. We did not do any non-fiction on this list. Yeah, I don't know. To me, from the moment I saw it, I was like, this is so fucking major. This, like, hit me right in the heart. And it does seem like the people who, like, the real ones know. Yeah. But it doesn't totally.

I hope this will be like an act of celebration, preservation, whatever you want to call it. I hope so as well. It does tickle me a little. To surprise? Well, yeah. You know, I was kind of like, I don't feel like this is celebrated enough. And so as all the other lists went by and people were sleeping on it, I was like, oh, we get to have this special moment.

I agree. I agree. Because I think it really is a special movie. I'm grateful that you can have that feeling without it feeling like you're pulling a trick or something, you know? Right. I don't want to troll. Well, and that's why we switched it.

It used to be a number two and now it's a number three. Now it's a number three. I feel good about that. Okay, so we mentioned Inside Man is what this is standing in for. I wrote down some other 21st century movies that are set in New York City. Yeah. So Francis Ha, which came up in our Lady Bird conversation, of course. Good Time and Uncut Gems, the Safty Brothers movies.

I think if we were, if we were going to go to the, the next New York movie, I probably would have picked Uncut Jems. I think that's valid. That's definitely in the like 25 to 30 range for me in terms of just like the most fun I've had with a movie. I'm with it. Another version of living in New York is kind of the uncut jams anxiety. If Beal Street could talk, Barry Jenkins's movie, which is a very good New York film,

Synecatee, New York. Requiem for a dream, which, you know, was kind of paired with this, a movie about drugs and paranoia. Yeah. Did you write in Margaret? I just put Margaret in. That's when I scrolled out because just Anna Pacman being a nightmare teen. Oh, yeah.

This was quite a run. In New York. Yeah, right on the heel, right on the verge of true blood. Yeah. And then drug dealer movies, like, I was never going to put any of these movies on the list, but American Gangster, Traffic, Blow. Yeah. There was an era from 2000 to 2010, especially during the rise of like a very specific kind of New York,

East Coast-centric era in hip-hop. Yeah. Where the glorification, the kind of scar-facedification. of a certain kind of drug dealer movie was happening. This is not that. No. This is a much sadder movie than that, but it is at least in relationship to it.

So speaking of recommended, if you like, a couple titles. Carlito's Way, I think, would be a great double feature with this movie. Brian De Palma's drug dealer movie about Al Pacino's character. Clockers, the Spike movie, which is also about drug dealers.

Kind of the different side of that story, like, you know, black kids in the projects as opposed to a white kid working for the Ukrainians. Boys in the Hood, which is a movie about high school friendship and about how

it can get broken up pretty quickly. Train spotting, also a friendship movie centered around drugs. Midnight Express or the darkest version of this story.

Once Upon Time in America, people committing crime in New York, Midnight Cowboy. Anything else? I always think about how Chris Ryan compares the ending of Lady Bird to this ending.

They're very, very different movies in every single way, but since we had ladybird recently on our list if you're into that bring it on over that's interesting yeah i guess there's something to that that sort of like the open-endedness yeah and the and the separation from reality and and like what's actually happened and like the wishfulness or the wistfulness you believe that monte while he is sleeping is on his way to odysville or do you believe he's on his way to albuquerque i think he's on his way to otisville i think so too yeah that's why you

and i are cynics um any closing thoughts Feeling good about three? I love this film. Me too. I mean, it's a gut punch in the best way every time, but it's a treat to rewatch it. I agree. I was happy to talk to you about it. Thanks to our producer, Jack Sanders, for his work on this episode.

Later this week, we have a post- Thanksgiving treat. We built the Robert Redford Hall of Fame with our friend Tracy Lutz. We sure did. You did the work. He did the work. He watched. He watched old TV episodes. And we did our best to build.

it. We've zagged a couple times. I feel good. I feel good about it too. We'll see you then.