Twenty Years of ’25th Hour,’ a Film That “Gets Bigger in Stature Every Year”

Spike and writer David Benioff reflect on making the Ed Norton crime parable that stands as the most visceral depiction of 9/11-aftermath New York City.

Barry Pepper Edward Norton and Philip Seymour Hoffman in 25th Hour 2002.

Barry Pepper, Edward Norton, and Philip Seymour Hoffman in 25th Hour, 2002.Everett Collection / Courtesy of Walt Disney Co.

Spike Lee felt insulted. In the weeks and months following the the tragic events of September 11, 2001, Hollywood engaged in a comprehensive sanitization process, cutting out glimpses of the World Trade Center from upcoming New York-set movies like Zoolander and Mr. Deeds, as well as a trailer for the first Spider-Man.. “Like it never existed,” Lee tells GQ over the phone. “Like New Yorkers or Americans aren’t strong enough to see the image of the World Trade Center anymore, which I thought was fucking ridiculous. I thought that was weak.”

In January of 2002, Lee had begun reading the script for what would eventually become his 14th film: 25th Hour,  a drama that future Game of Thrones showrunner David Benioff had adapted from his novel published the previous year. The film follows Monty Brogan (Edward Norton), an Upper East Side drug-dealer, on the day before he must report for a seven-year stint at an upstate penitentiary. In his final hours, he shares a steak dinner with his father (Brian Cox), meets his two best friends, Jacob and Frank (Phillip Seymour-Hoffman and Barry Pepper), and girlfriend Naturelle (Rosario Dawson) at a club for one last big night, and then ties up loose ends with his nefarious business partners. Moved by Monty’s regrets and reconciliations, and living in the aftermath of catastrophe, Lee began thinking bigger. “This grieving, post-9/11 New York City could be a character in this film,” he thought. “I always felt art should reflect what’s happening at the time. I was not going to run from that stuff. Hell no.”

At first, Benioff was skeptical of that plan. He’d written the book and the first several drafts of his script before the attacks, and “didn’t want to be involved with anything that might seem to be exploiting a tragedy that took thousands of lives,” he says in an email. But Lee didn’t want to explicitly address the attacks; instead, he dexterously infused the city’s quiet, shaken mood into this 24-hour morality tale, contextualizing Monty’s decisions and self-reckoning with the visceral attitudes and imagery attached to that fateful day, like the Tribute in Light beams, FDNY memorials, and newspaper headlines. “Spike handled a difficult topic adroitly—he took on the [city’s] reality with all its dread and defiance,” Benioff says. “A lesser filmmaker would have cheapened it.”

Twenty years after its release, 25th Hour remains the best and most accurate depiction of a post-9/11 New York City—a time capsule exuding the city’s love-hate relationship with itself and the wounds it combatted every day, which Lee exemplified in one of the most memorable scenes of the 21st century. It also continued to affirm the director’s bold vision for connecting character and place, and his innate desire to share unvarnished depictions of his hometown. “This was about the soul of New York City,” Lee says. “I made this film for New Yorkers and I think they understand this is about them—this is for them.”

The idea for 25th Hour emerged from Benioff’s failed 1995 novel Wag, “which was rejected by every publisher in America,” he writes. Once he’d digested several editors’ critiques, which argued that his story was misshapen and bloated, he resolved to write a shorter book that would span “weeks, or days, or hours,” instead of decades. He’d already written a story in that vein in college, effectively the penultimate scene of 25th Hour, about a character asking his friends to beat him up on the East River Esplanade so he looks ugly when he enters prison. “I decided I wanted to see what the previous day had been like for these friends,” Benioff says. 

After he found a publisher in 1999, Tobey Maguire read the manuscript and optioned the story with his production company. The actor, who initially planned to play Monty before being cast in Spider-Man, then asked Benioff if he’d like to adapt the novel himself. Upon the script’s completion, Lee, who shared the same agent as Benioff, paged through it and asked to read the novel, which he littered with Post-it notes and scribbles. “He told me he loved the book, but I’d left out too much of the good stuff, that the script didn’t have the same impact on him as the novel,” Benioff says. 

Lee was mostly referencing a discrepancy that would become the movie’s seminal scene—the “Fuck you!” monologue in which Monty eviscerates every imaginable New York City stereotype and demographic while staring into a bathroom mirror. What begins as a loud projection of Monty’s own insecurities and mistakes eventually turns into a moment of accountability and introspection, a pivotal coming-to-terms clarity with his imminent imprisonment. “I said, ‘David, how come this mirror scene is not in the script?’” Lee remembers, to which Benioff replied: “I didn’t know how to make the monologue cinematic.”

“He shook his head and said, “Let me worry about making it cinematic,” Benioff adds. “I put the scene in the script and he and Edward made it cinematic as fuck.”


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The scene takes place about halfway through 25th Hour, as Lee cuts between grainy shots of the various ethnic communities, professions, neighborhoods, and classes of the city as Monty drops F-bombs about each of them over an elegiac Terence Blanchard score. He Monty works to a crescendo of “Fuck this whole city and everyone in it. Let earthquakes crumble it, let the fires rage, let it burn to fucking ash and then let the waters rise and submerge this whole rat-infested place,” before closing by snapping back at himself: “No. Fuck you, Montgomery Brogan. You had it all and you threw it away.” 

It’s a mesmerizing, feverish five minutes, reminiscent of a scene in Do The Right Thing, when Mookie and Pino get into an argument that devolves into dueling, racist descriptions of residents on their Brooklyn block. This scene, however, was “bigger and grander,” Lee says, extending to: the “Bensonhurst Italians…swinging their Jason Giami Louisville Slugger baseball bat trying to audition for The Sopranos”; the “uptown brothers” playing basketball who “never pass the ball, they don’t want to play defense, they take five steps on every layup to the hoop, and then they want to turn around and blame everything on the white man”; and pedophile priests, “the Church that protects them,” and “J.C., he got off easy,” the list accompanied by a shot of St. Patrick’s Cathedral. (He laughs that  he presumed a lightning bolt would strike him down for it.) “[The speech] shows this relationship that we New Yorkers have with other people,” Lee says, noting the tensions of the city in the aftermath of the attacks. “Even though those things are mean and nasty and evil, in a way, the level of ignorance is funny. That’s what makes New York City New York City. This shit is mean, and it ain’t for everybody.”

Benioff conceived the monologue while reading a Christopher Smart poem, in which every line begins with the word “For.” Intrigued by its off-kilter rhythm, he “thought it would be interesting to hear Monty’s fury at his circumstances expressed in the form of a kind of manic monologue.” And yet, despite its vulgar nature, “it’s also a kind of Valentine for the city.” In many ways the rant is microcosmic of the movie itself, leading to a moment of self-awareness and personal responsibility. “He comes to the realization that it wasn’t those people, it was him—he’s the one that fucked up,” Lee says. “[He] had to be a man and take the blame.” 

Though it functions like a short film, the monologue fits into the atmospheric tone of tragedy that Lee and Blanchard had been building throughout the movie. In the opening credits, cinematographer Rodrigo Prieto captures a montage of the mournful Tribute in Light, the art installation that projected 88 searchlights into the sky to memorialize the fallen towers. They lit up Manhattan for five weeks, beginning in March of 2002, but Lee “didn’t find out about it until the last day,” he says. “I called up Rodrigo: ‘You’ve got to shoot this.’”

Lee was similarly assertive about a dialogue scene between Frank and Jacob, which he wanted set in front of a window with views of Ground Zero. The characters’ discussion becomes overwhelmed by the scenes below them of construction workers sifting through the wreckage for human remains, and in one fluid shot their conversation shifts from their own personal issues to a debate about which newspapers told the truth about the air quality. “At that time, that area was shut down,” Lee says. “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.”

Edward Norton, Philip Seymour Hoffman, and Spike Lee in 25th Hour, 2002.Everett Collection / Walt Disney Co.

Though Benioff thought of a couple different options for a finale to his script, but ultimately chose to keep the novel’s ending, in which Monty’s father takes his son to prison the next morning and imagines driving him west to start a new life under a new name. It’s a beautiful alternate sequence, narrated by Cox, which brings back some of the original faces from the mirror monologue—a suggestion Norton made to Lee to cast them in a more positive light. “That’s what happens when your life goes in front of you—you think about your missteps,” Lee says, “and that’s what this film’s about: this last day of freedom, if I’d have done this, or that.”

Benioff had been inspired to write the dreamlike sequence after meditating on Ernest Hemingway’s last line in The Sun Also Rises: “Isn’t it pretty to think so?” But for New Yorkers and those impacted by 9/11, the thought experiment extended into the reality of their city—what if the attacks had never happened? How might their lives be different? “I’m glad we got back to the original concept,” Benioff says. “Edward and Brian Cox—it’s hard to imagine two better actors for a two-hander.” 

Despite the movie’s lack of awards prestige and minimal box office, Lee’s movie has only gained more reverence and appreciation over the last two decades. Roger Ebert and A.O. Scott each put the movie into their respective best of the decade lists, while film critic Mick LaSalle likened it to Rossellini’s Open City, calling it “the only great film dealing with the Sept. 11 tragedy.” Tapping into his documentarian instincts, Lee never flinched. On the precipice of a new era, he showed the city in its traumatized state, engaged with its frequently painful memories, and zigged while Hollywood zagged. “That’s the kind of filmmaker I am,” Lee says. “Films can fade away, but I’m very fortunate this film gets bigger in stature every year.”

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