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

0:28I'm Sean Fennessey. 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, Philip Seymour Hoffman, Barry Pepper, Rosario Dawson, Anna Paquin, Brian Cox, a number of Spike Lee all-star character actors. It's shot by Rodrigo Prieto, 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.

1:04So 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 Reilly 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.

1:37And 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.

2:09And you, 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, but you know, that was kind of the idea.

2:49But 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. I know, we never discussed, we never strategized around this. Yeah, so why do 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.

3:23This is probably revealing some, the direction of where we're headed on the list, but I think most fans of the show and 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.

3:59And 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. As a senior in high school, yeah. It's 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.

4:41And 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, Moe 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.

5:20But maybe not ever, maybe it has not been distributed in quite the same way. 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. It's true. Yeah, I guess it's an unspoken masterpiece.

5:50Not 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 a 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. Exactly. It was like the death, the irony of 9-11, and then it resurged and became even more messed up.

6:37So 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 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 good or important or how we were processing things or even the types of films we wanted to see really changed.

7:30And so I think it just got lost a bit in the shuffle of a reinvention of our understanding of Hollywood American output in the early 2000s. I think that's right on the money. this is also the time of Sam Raimi's Spider-Man movies which were also New York set movies about heroism and that there was something I 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 Tobey Maguire who produced this movie and who is 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.

8:15This is a movie that very much leans into the specifics of the event. It's not a movie about 9-11. 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 Naturel. 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.

8:51And 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 has a great energy and vitality to it. And it does have a sense of humor, but 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 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 fuck you 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.

9:41It 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, I consistently cry at the end of the movie. Yeah. And there's not a lot of movies that I can see on eighth time and still feel very moved by. I try it something different every single time. Yeah, at a moment. Yeah, yeah, yeah. In the conclusion, yeah. It's funny, there's definitely, this is going to be one of the lesser seen movies, I think, in the top 10. And there are probably people listening to the episode who have not seen this movie.

10:10I 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.

10:42I hadn't even thought about that. We talked about it a bit in terms of, at the selection 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, 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.

11:21And sometimes when they're in his world, it can feel a bit like a closed loop. I find 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.

11:52It reminds me a little bit of 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. 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, where he just kept asking Spike Lee, like, when's the double dolly shot? When'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. um 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 is truly like when two great minds and two great skill sets like meet and elevate the other.

12:56And 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, OK, 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 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.

13:30So he is, in 2002, at the absolute center of Hollywood. He's 32 years old. He's already had two acting Academy Award nominations. He has gone from wonderkind, 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 Salma Hayek 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 Tobey Maguire thought he might play this part. He had a conflict with Spider-Man and it eventually became an Edward Norton movie.

14:17And 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 Milos Forman 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.

14:54Sure. 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. 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, 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.

15:57That's what it is. Yeah, it's an internal monologue that is made external. 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 a self-loathing or self-frustration or self-pitying. but but also this is that segment is a love letter to New York also in like it is filled with like hate speech and is like is very ugly and relies on stereotypes and is also written in a way that observes and understands how New York works and 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 like 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.

17:08But it's written from such like a knowingness and observation 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 Bran, Like there usually is in Brando. It's just, 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 comes from seemingly a lower middle class background. And he fucks up because he starts dealing drugs in school.

17:48He 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 this sense of my, 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.

18:28It 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, 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. 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 bombs that the United States was dropping on places that were not the United States in some sort of, like, I don't even remember where, which is one of many parts of the problem.

19:14Totally. 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 manifests all of those feelings that people were having. And at no greater moment, I think, than in the fuck you rant that he gives. 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 Philip 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 times I read the New York Post just like iconic Barry Pepper stuff What happened to Barry Pepper?

20:13I don't know. I Googled that last night. He's so extraordinary in this movie. He's so good in this. And then the conversation turns to Monty. And it goes from 9-11 to Monty's 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.

20:58Totally appropriate for the big swells that he is known for. But and I was just like, oh, so it's literally it's over after. 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, there'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.

21:32And 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, a frictive 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.

21:59But 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? Like, 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.

22:29And 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 got to be one guy who's like, I'm the empathetic guy. But then people's personalities merge and they split apart. And as I was watching the movie very closely, I was like, ah, 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.

23:00They're the ego and the super ego and the id. You know, Monty is the ego, Frank is the super ego, and, 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?

23:33What 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. You're confronted by it on a regular basis. Right. And so, this is a very familiar version and a very perceptive version of what I am confronted with with a bunch of guys who, 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?

24:13Don'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 some time. But I was thinking last night about our conversation around the movie Friendship, the 20 and 25, 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.

24:53Yes. 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. This episode is brought to you by Amazon Prime. Like an action blockbuster, the holidays move quick. But with Prime, fast free delivery means those last-minute gifts arrive right when you need them. Last year, while watching Stingin' in the Rain with my son, I realized a pair of tap shoes would be a perfect Christmas gift, and I had them under the tree for him on Christmas Day. Prime's fast shipping is always there for you during the holidays, especially when it's last minute and just can't wait.

25:29Last 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 and 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.

26:14And so for some of the film, he feels that Naturelle, 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.

27:05You 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-Fentanyl, 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.