25th Hour (2002) and a final farewell to Philip Seymour Hoffman (part 4)
“I want to be like that girl from X-Men. The one that can walk through walls”

“A Spike Lee Joint” will mean many things to many cinema goers for the Atlanta born filmmaker who when not busy writing, producing and directing 23 feature length films, at the time of writing, is forever courtside at his beloved New York Knicks, watching the city’s ice hockey Rangers or sitting near home plate and wearing the distinctive blue cap of the New York Yankees. Nearly four decades since his debut feature She’s Gotta Have It in 1986, we will all have our own respective favourite creations with mine bookended by my first Spike Lee Joint Do The Right Thing in 1989 and BlacKkKlansman nearly three decades later and in between, four true cinematic gems: Mo’ Better Blues and Malcolm X in the early 1990’s, the underrated Inside Man in 2006 and four years before, the forever magnificent 25th Hour.
Created and filmed in the dark shadow of 9–11 and dedicated to a stream of local New York firefighters who lost their lives in the immediate aftermath of the terror attacks, 25th Hour is soaked to the bone with grief and loss and a melancholic, paranoid tale of having and losing everything and a mistrust of everyone surrounding a somewhat singular man spending his final 24 hours of freedom before spending the next seven years in the prime of his life in prison. That man is “Monty Brogan” (Edward Norton) a drug dealer betrayed by someone in his inner circle and whilst he spends his final day of freedom on the streets of New York and saying a raft of goodbyes to his father “James Brogan” (Brian Cox), bodyguard “Kostya Novotny” (Tony Siragusa), childhood friends “Jacob Elinsky” (Philip Seymour Hoffman) and “Frank Slaugherty” (Barry Pepper) he’s somewhat avoiding a final farewell to long term girlfriend “Naturelle Riviera” (Rosario Dawson) as he seeks the ultimate answer to the anger engulfing him and the life he ultimately destroyed: Who betrayed him?
Anger is as obvious a through line for the film as friendship, loyalty and betrayal, a father’s love for an errant child, paranoia, deceit, trust and, I’d argue, loneliness and being alone, as I saw every character in this magnificent film (despite its overall deeply melancholic tone) as being alone with everybody, surrounded by everyone they trust with their innermost feelings and desires and yet, still alone. Combining two themes and the anger of loneliness, this is brilliantly and horribly realised early in the film as Monty, staring at a bathroom mirror in his father’s bar, spots “fuck you” scrawled in the corner of the mirror. This sets off an eruption of anger from Monty at everyone and anyone, anything and everything in the multicultural city of his birth, his own multicultural lifetime relationship with Naturelle, his father, friends, enemies and customers, as well as a rage fuelled fuck you to every creed and colour, nationality, ethnicity, community, sexuality, race or religion and in short, everyone, alone with everybody once more, and even an angry dismissal of himself last of all and “you had it all and you threw it away you dumb fuck”. Edward Norton is your headline star of the show and ably supported by the sunshine to his regret filled melancholia by the always beautiful Rosario Dawson and as I hope I outline briefly below, vital supporting roles too from Brian Cox and especially Barry Pepper. But as this is an ode to joy for the acting magnificence of Philip Seymour Hoffman, I’ll conclude with my praise for 25th Hour by highlighting the largest supporting role of all here and, in line with the general theme of the film, Philip’s portrayal is of a man crushingly lonely, disconnected from the friends he’d entrust his life to and yet, even when in their company, still alone with everybody.
“Jacob Elinsky” (Philip Seymour Hoffman) Jacob is a painfully repressed high school teacher inappropriately besotted (and borderline obsessed) with his young literature student “Mary D’Annunzio” (Anna Paquin) and whether alone with Mary, or Monty or more regularly his childhood friend Frank (a thoroughly repugnant Wall Street trader and brilliant portrayal in the ruthless and selfish pursuit of money by Barry Pepper) Jacob remains an awkward outsider and alone with everybody. Continuing a theme once more, Jacob is often left alone, be it the ringing of a school bell to end his lesson and with a sigh, he’s alone again, or the very next scene and now awkwardly and inappropriately alone with Mary in the teacher’s lounge, she leaves him, alone and sighing once more, when her flirtatious behaviour will not be rewarded with a desperately needed higher grade. From his staid and age appropriate attire of a school teacher, Jacob spends the rest of the movie dressed as though he were a high school or college student himself, yet he remains painfully shy and awkward even with friends he’s grown up with and comfortable around, left alone in a nightclub of his nightmares by first Monty and then Mary and then, with trademark Spike Lee riding dolly shot, framed up close, rolling and reeling from a nightmare that may be his undoing, and all alone. With everybody.
Numerous scenes veer away from this theme but spoilers aside, I’ll conclude with one which encapsulates many of the film’s other through lines as Jacob joins Frank for a pre-night out beer in his apartment, and a high-rise apartment with a window onto a world of utter devastation and a Ground Zero immediately after the terrorist attacks of 9–11. Jacob and Frank may well be friends of nigh on three decades and back to their earliest years of forming memories but they’re estranged, strangers even, and two disparate New Yorkers sharing a beer overlooking a heartbreaking backdrop, alone even with a friend beside them and one trying to keep a rational balance for the night ahead and the other? A cold, distanced and angry trio of choices for his best friend. Either Monty can run, hit the “bullet train” or take his chances in the face of betrayal and head to prison.
I first watched 25th Hour immediately on DVD release over two decades ago and I adored it. Last night’s re-watch only enhanced my cinematic love for one of Spike Lee’s greatest feature length achievements.
Highly recommended.
Thanks for reading. I hope this message in a bottle in The Matrix finds you well, prospering, and the right way up in an upside down world.
Whilst you’re here I may as well brag about the release of my trilogy of recently self-published books. Beautiful covers eh! As the title(s) would suggest, this is my life at the movies or at least from 1980 to 2024, and in volume 1 you’ll find 80 spoiler free appraisals of movies from debut filmmakers, 91 of the very best films appraised with love and absent of spoilers from 1990–2024 in volume 2, and in volume 3 you’ll find career “specials” on Paul Thomas Anderson and Quentin Tarantino together with the very best of the rest and another 87 spoiler free film reviews from 2001–2024.
All available in hardback and paperback and here are some handy links:
"A Life at the Movies Vol.1" - link to Amazon
"A Life at the Movies Vol.2" - link to Amazon
"A Life at the Movies Vol.3" - link to Amazon
One of my favorites. I rewatched it in prison in 2014, where it obviously hits differently. That fantasy finale of his father driving him to a nowhere town to start again just devastated me, such a powerful show of love. And, unfortunately, if you know New York, that final driving sequence reveals whether it's a fantasy, or if it really happened.
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