Spike Lee’s ‘25th Hour’: A Masterful Depiction of a Post-9/11 New York City that Explores Regret, Guilt and Uncertainty

April 26, 2023


By Koraljka Suton

In 2000, New Yorker David Benioff, who would go on to become one-half of the Game of Thrones showrunning duo, penned a novel called Fireman Down. Unfortunately for him, the manuscript wasn’t met with a lot of enthusiasm, with thirteen publishers passing on the prospective author’s first book. But after six months of futility, just as he was coming to terms with his fate, the future screenwriter caught his lucky break after all. An editor was intrigued, but would buy the novel only under the condition that the title underwent a make-over. Thus, Fireman Down became The 25th Hour. And since life is more often than not stranger than fiction, what followed was something Benioff couldn’t have conjured up in his wildest dreams, no matter how good of a writer he was.

In an exciting twist of fate (or dare I say plot twist), half a year before the book was even published, the preliminary trade copy started making rounds in Hollywood and ultimately found its way into the hands of Tobey Maguire. The actor expressed interest in playing the role of the protagonist, optioned the script with his production company and asked Benioff to adapt his own work. But even though he had never written for the screen before, the author nevertheless jumped at the opportunity because the WGA (Writers Guild of America) minimum he would be getting paid was eight times the amount he had earned from book sales. Still, money wasn’t the only incentive Benioff had to say yes to a job he hadn’t done before. In his 2003 Guardian piece, he wrote the following: “I did not want some Malibu surfer inventing dialogue for my New Yorkers. I didn’t want to see my baby abused by one of those guys in black-framed glasses who spends his afternoons at Starbucks, drinking lattes and typing treatments.”

Three months later, the first draft was finished (plus, the ‘the’ in the title was dropped) and Benioff was eager to get script notes from the producers. A second draft was in order, because it turned out that he didn’t deviate from the book in terms of structure. But after doing “what was best for the script” as opposed to “keeping faith with the novel,” as Benioff himself put it, the producers ate it up and started looking for directors. Every single one of them declined the offer. To add insult to injury, Maguire decided to bow out due to getting cast as the cinematic iteration of beloved teen superhero Spider-Man in Sam Raimi’s 2002 film of the same name, but still remained on as producer. And just as Benioff started to think that that was all she wrote, he was told someone wanted to direct the film after all. And that someone was Spike Lee. The filmmaker had the same agent as the writer and, after reading the script, eagerly picked up the source material. It’s a good thing he did though, because the director had a thing or two to say about certain changes Benioff had made while turning his own novel into a screenplay.


In 25th Hour, we follow a day in the life of Upper East Side drug dealer Monty Brogan (short for Montgomery—his late mom was a big fan of Montgomery Clift), portrayed by Edward Norton. It’s not just any given day, but his last twenty-four hours of freedom before he has to report to prison for the next seven years. What our protagonist fears the most is his first hour behind bars (the 25th hour), because he is well aware of the fact that pretty boys like himself don’t fare well in one such setting. But even though Monty is the only one getting locked up, the people closest to him are all heavily impacted by this change to the status quo. His live-in girlfriend Naturelle (Rosario Dawson) wants him to open up to her, but Monty remains distant and closed off, suspecting her of being the one to have ratted on him. His father James (Brian Cox), an ex-fireman and current bar owner, feels remorse and guilt for setting up the place with his son’s drug money. Monty’s two best friends—crude Wall Street trader Frank (Barry Pepper) who sees himself as God’s gift to women and shy high school teacher Jacob (Philip Seymour Hoffman) with a crush on a free-spirited student (Anna Paquin)—hold opposing viewpoints on Monty’s predicament and its implications for their friendships.

What is fascinating about Lee’s character-driven drama is the amount of time and space it gives to the supporting characters (most notably Frank and Jacob), presenting us with a variety of ways in which one can cope when forced to swim in uncharted waters. We not only get to see who they are as people outside of their relationship with the protagonist, but we also learn a lot about what makes them tick thanks to how they respond to the prospect of Monty’s incarceration. Their thought processes, the ways in which they interact with both Monty and each other, the decisions they make based on how they feel about the inevitable—all of this gives depth and complexity to the characters. It fleshes them out, while at the same time providing viewers with the opportunity to ask themselves how they would feel and what they would do if they had to walk a mile in those shoes. If they were the loyal girlfriend, the guilt-ridden father or the judgmental childhood friend of a person who earned big bucks by selling heroin. If they were the ones who knew all along, maybe even profited off of it, but said nothing. And Monty? While the people orbiting him come to terms with his fate each in their own way, the protagonist spends his last day trapped in his own little microcosm of worry, regret and angst. Even when he does engage with those around him, he is never truly there. His impending doom renders him unable to meaningfully connect to the people he loves and who love him back. And no one can blame him for it. We most certainly wouldn’t want to be in his shoes.


But what makes 25th Hour a stand-out feature film is the fact that the “grieving, post-9/11 New York City,” as Lee called it, becomes a prominent character in its own right. Filming hadn’t yet begun when tragedy struck in the form of the September 11 attacks. Deeply impacted by what had come to pass, Lee decided not to shy away from it, but rather make it an integral part of the film, seeing as how it was already an integral part of the collective New Yorker experience. And he always thought that art should be a reflection of the zeitgeist. Benioff was apprehensive at first, saying that he “didn’t want to be involved with anything that might seem to be exploiting a tragedy that took thousands of lives,” but what Lee ended up doing was the polar opposite of exploitation. The attacks are never mentioned or talked about, nor do they need to be. We know when the story takes place not because of anything that is said, but because of everything that is shown. The Tribute in Light art installation that represents the Twin Towers. Newspaper headlines. A memorial of fallen firefighters on the wall of James’ bar. An entire conversation taking place in front of a window in Frank’s apartment overlooking Ground Zero—as Jacob and Frank discuss the future of their relationships with Monty (or a potential lack thereof), we witness construction workers excavating remains. Post-9/11 New York is a somber, devastating reality for its citizens—both real and, in this case, fictional. Monty’s individual reality plagued by uncertainty and drenched in helplessness, fear and dread is just an extension of it.


When talking about securing the location for the aforementioned scene between Jacob and Frank, Lee said: “At that time, that area was shut down. I told the location manager I need a space that looks directly over Ground Zero. I don’t care how you get it, whatever lies you’ve got to tell, I don’t give a fuck. I need a window to look directly down upon Ground Zero, and he got it.” This uncompromising attitude of Lee’s that ultimately enabled him to shoot one of the most significant and nuanced scenes in the film, was not the only time the director put his foot down and boldly went for what he wanted, no matter the potential obstacles or cost. Remember when I mentioned that Lee wasn’t exactly thrilled about the changes Benioff had made when adapting the source material into a script? Well, there was a scene that the screenwriter purposefully omitted from the screenplay, thinking that it wouldn’t transfer well to the screen, not knowing how to make it cinematic. But Lee knew better: “Let me worry about making it cinematic,” he told the screenwriter. And make it cinematic he did. I am talking, of course, about what became known as the “Fuck you!” monologue. A scene that Disney didn’t want included in the film. But Lee included it anyway. As Benioff described it: “The Disney executives had one complaint: cut the monologue. Spike and I resisted. I wrote a note explaining my interpretation of the scene, why it was vital to the story, why the soliloquy should be seen as a paean to New York and not a barrage of ethnic prejudice. Spike—well, Spike resisted by just shooting the damn scene.”

Benioff first came up with it while he was reading a poem written by 18th-century English poet Christopher Smart. In it, every line starts with the word “for,” resulting in an unusual rhythm that fascinated Benioff. So, he decided that every line in Monty’s monologue would start with “fuck.” Simultaneously an angry rant and “a kind of Valentine for the City,” as the screenwriter himself put it, the “Fuck you!” monologue is Monty’s way of unapologetically slamming every possible NYC demographic, people of every ethnicity, sexual orientation and creed (including his friends, father and girlfriend) and distributing blame before eventually admitting to himself (and to us) that he is the only one responsible for his mess. That he is the one who deserves a “fuck you.” Norton provides a master class in acting, as Monty’s reflection delivers the angry five-minute rant, while the protagonist is staring at himself (and at us) in the restroom mirror in his father’s bar. And, as David Fear of Rolling Stone pointed out: “But the scene also plays as a love letter, in its own way, to everything that’s characterized New York for this out-of-luck dealer. These are the people and things he hates about New York. This is who and what he’ll fondly miss when those prison doors slam shut. Should you doubt the double meaning, Lee reprises many of these types as Norton drives off to his fate, waving as he passes by.”


The essence of NY street life was perfectly captured by esteemed cinematographer Rodrigo Prieto (three Academy Award nominations—Brokeback Mountain (2005), Silence (2016) and The Irishman (2019)), who had collaborated with Lee neither before nor since. And 25th Hour wouldn’t be a Spike Lee film without his signature cutaways, jump cuts, spliced takes of the same shot repeated sequentially and, of course, his trademark double dolly shot, whereby both the characters and the camera are placed on a dolly, making it seem as if they were gliding in midair. In this film, the double dolly shot is used on two occasions: when Jacob’s student is dancing on ecstasy at a club, giving off the impression of her having an out-of-body experience; and right after Jacob kisses her and runs off in disbelief over what he had just done, signaling his confusion and lack of inner stability.

25th Hour was by no means a box office hit, partly due to its lack of an appropriate marketing budget and in part, according to Guy Westwell of Mapping Contemporary Cinema, because the American public wasn’t ready to witness a scarred New York and instead opted for escapism in the form of more mainstream cinema. But as time went on, 25th Hour unequivocally became “the best and most accurate depiction of a post-9/11 New York City” and still holds that title even twenty years after its original release. In Lee’s own words: “This was about the soul of New York City. I made this film for New Yorkers and I think they understand this is about them—this is for them.” But even if we were to somehow look beyond the NYC context that makes up the film’s DNA, 25th Hour would still function as a wonderful piece of cinema masterfully exploring the universal concepts of guilt, regret and uncertainty.

Koraljka Suton is a member of the Croatian Society of Film Critics and has a master’s degree in German and English. For her thesis, she did a comparative analysis of Spielberg’s ‘Band of Brothers’ and ‘The Pacific’. Koraljka trained at a Zagreb-based acting studio for six years and fell in love with Michael Chekhov and Lee Strasberg’s acting techniques. She is also a contemporary dancer and a Reiki master who believes in the transformative quality of art. Read more »


So when I found out I’d be working with Spike Lee I was ecstatic, and it felt very surreal because there is no director who is more a New York director. When you think of New York directors, you think Woody Allen, Scorsese, and Spike, and certainly Woody Allen I don’t think would ever make a movie like ’25th Hour,’ that would be bizarre. And he also got Rodrigo Prieto, who is not a New Yorker, but is so good at filming urban landscapes. It was a really good experience all the way around and we never had any friction, partly probably because I was just so happy to be there. —David Benioff

Screenwriter must-read: David Benioff’s screenplay for 25th Hour [PDF]. (NOTE: For educational and research purposes only). The DVD of the film is available at Amazon and other online retailers. Absolutely our highest recommendation.


Spike Lee’s filmmaking career is examined in this partial making-of for the film 25th Hour (2002). Interviews with cast members from this film and his past successes give us an idea of what kind of dedicated person he truly is.

Spike Lee and Edward Norton talk about collaborating on 25th Hour, in which Norton plays a drug dealer on his last night before his incarceration.


“When we were doing [25th Hour], Phil Hoffman and I talked about how much Do the Right Thing changed our goals. It changed our aspirations for the kind of work we wanted to do because it was so… joyful, it was so funny, it was so entertaining. But it was also this really serious dive into some of the thorniest issues of American life. [Lee] was this kid. He was, like, a couple of years out of film school, and he writes and produces and directs and stars in this movie about his neighborhood, and it’s one of the greatest American films of the last fifty years. It was like, ‘Holy crap, what a swing. What an amazing, audacious, original thing—and it’s serious, too.’ It was like, ‘That’s what you’re going for.’ So we came on to [25th Hour]… pretty steeped in Spike.”


25th Hour director Spike Lee on a filmmaker’s body of work.


Director, writer, actor, producer, author, and NYU Grad Film Tenured Professor Spike Lee has an incredible career, winning awards from all over the world and with a pioneering body of work that has spanned over thirty years. He has, in particular, chronicled Black lives through bold and inventive cinematic works of art from feature films and documentary to television, music, commercials and books. Here he talks with fashion designer Ozwald Boateng about his career to-date.


Philip Seymour Hoffman talks about getting into character, acting in his brother’s screenplay Love Liza, and working with Spike Lee.



“Oh man, the challenge there for the 25th Hour as me and Spike Lee talked was to never let the audience forget that this was a post 9/11 New York. That’s why you have the Arabic sounds, the bagpipes and the Irish instruments throughout the score. Certain areas had certain sounds that painted the backdrop of this post 9/11 city. Spike of course did it cinematically by including fire trucks with people still cleaning up debris around the Twin Towers. A great deal music served as a painting of a picture in time.” —Terence Blanchard



The list of directors Rodrigo Prieto has worked with reads like a list of the greatest directors currently working: Martin Scorsese, Pedro Almodóvar, Ang Lee, Oliver Stone, Spike Lee, and Alejandro Iñárritu, to name a few. The acclaimed director of photography started in the independent film scene in Mexico, and first gained international attention in 2000 with his work on Iñárritu’s Amores Perros. How has Prieto now become one of the most coveted cinematographers of the past twenty years? The answer lies in his inimitable detail-oriented style and collaborative approach. —Rodrigo Prieto Style

Rodrigo Prieto’s aesthetic and approaches are chronicled from his early days to the present in the following video from Sareesh Sudhakaran for Wolfcrow, where he is swiftly becoming one of the field’s most sought-after shooters.


Rodrigo Prieto on his use of “subjective cinematography” techniques to tell an emotionally resonant story.


Here are several photos taken behind-the-scenes during production of Spike Lee’s 25th Hour. Photographed by David Lee © Touchstone Pictures, 25th Hour Productions, 40 Acres & A Mule Filmworks, Gamut Films. Intended for editorial use only. All material for educational and noncommercial purposes only.


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