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

Podcast: The Big Picture (The Ringer)
Hosts: Sean Fennessey and Amanda Dobbins
Episode Date: November 26, 2025
Film Discussed: 25th Hour (2002), dir. Spike Lee

Overview

In this special episode, Sean Fennessey and Amanda Dobbins break down Spike Lee's 25th Hour as their pick for the third best movie of the 21st century. They reflect on its underappreciated legacy, emotional resonance, and technical mastery, analyzing why it remains such a powerful, uniquely American film—especially as a cinematic time capsule of post-9/11 New York. The conversation also touches on the movie’s challenging themes, standout performances, and the role it plays in both Spike Lee's and 21st-century cinema.

Key Discussion Points & Insights

Why 25th Hour Ranks So Highly

• The hosts reveal that 25th Hour was originally #2 on their list but was recently swapped with another out-and-out masterpiece (03:13).
• This pick surprised fans and even close friends:

  "Our good friend Dan Reilly has been trying to guess for two weeks now...and he just struck out every time." (Amanda, 02:14)

The Movie’s Personal & Historical Context

• Sean and Amanda both cite their personal coming-of-age around the time of 9/11, and how 25th Hour captures a unique “present tense” atmosphere:

  "This is one of the most present tense films ever made...a story about a guy...in the aftermath of the attacks on 9/11. There's not really a lot of big scale corporately distributed works of art that are about this moment in history." (Sean, 04:09–05:22)

• Amanda observes the film's unique place, not forgotten but “requiring a jog to memory” due to its raw engagement with 9/11 and its aftermath (06:39).

Unflinching Portrayal of Post-9/11 America

• The movie serves as both a time capsule and immediate emotional outpouring for New Yorkers and Americans after the attacks:

  "It 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...I think we as Americans definitely repress." (Amanda, 07:00)

• Contrasts are drawn with contemporary films, such as Sam Raimi’s Spider-Man, which leaned towards hope and heroism (08:35).

Character and Thematic Depth

• 25th Hour isn’t "about" 9/11, but is set wholly within its shadow, exploring loss of innocence, flawed characters, and male repression.

  "You could make the case that every character in this movie is kind of a creep or a loser or somebody...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." (Sean, 08:35–09:59)

• The central character, Monty Brogan (Edward Norton), is described as a modern tragic figure:

  "He's like a Brando or like a Pacino character...but he has even tamped down the charisma. This is a really angry movie. But in the most famously angry scene, it's done through a mirror." (Amanda, 16:18)

Standout Scenes and Technical Masterpieces

• The "Fuck You Monologue" and the final “what if” sequence are hailed as two of the great filmmaking set pieces of the 21st century:

  "The writing and then the way that Lee adapts it and his particular style put to the subject of New York in the fuck you rant. And then the ending, which is...the best ending of a movie in the 21st century." (Amanda, 09:59)

• Frequent mention is made of Rodrigo Prieto’s cinematography and Terence Blanchard’s score, alongside Spike Lee’s signature stylistic choices ("double dolly shots," inventive color usage, and flashbacks).

  "With Spike, you've got Barry Alexander Brown cutting the movie...Terrence Blanchard, as you said, doing the score...But adding Benioff and adding Prieto, I just feel like lifts this movie above some of his other work." (Sean, 43:20)

Underappreciated Status and Legacy

• Despite being viewed as a masterpiece by many cinephiles and filmmakers, 25th Hour doesn't receive the mainstream celebration of other top-tier films, nor is it included in some major "Best Of" lists (e.g., The New York Times) (45:31).
• The film is seen as both personally and culturally resonant, especially for New Yorkers and those who entered adulthood in the early 2000s.
• Amanda values how the film’s relative under-the-radar status makes its fans feel like members of a special club:

  "As all the other lists went by and people were sleeping on it, I was like, oh, we get to have this special moment." (Amanda, 46:25)

Performance and Casting Highlights

• Edward Norton's work is described as a career-defining performance—subtle, internal, and distinct from his prior roles (15:48–16:50).
• The supporting cast (Philip Seymour Hoffman, Barry Pepper, Rosario Dawson, Anna Paquin, Brian Cox) all receive acclaim, with several “where are they now” asides (Barry Pepper, Tony Siragusa) (21:10–36:07).
• The "men who can’t express their feelings" theme is drawn out as a major storyline, both dramatically and comically.

  "This is really a movie about how men are with each other and how they kind of don't know how to tell the truth..." (Sean, 23:05)

• The impact of pairing Spike Lee’s vision with David Benioff’s source novel and screenplay is repeatedly emphasized as “elevating” the material (12:57).

Confronting Masculinity and Toxicity

• The movie is unflinching about the “perils of masculinity”—from statutory relationships to repressed anger and violence:

  "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." (Sean, 31:15)

• The shame, limitations, and self-sabotage of the male characters are depicted as integral to the story, especially via the character of Jacob (Philip Seymour Hoffman):

  "He's the embodiment of shame...He didn't get laid enough when he was a teenager and now doesn't know how to relate to women..." (Sean, 32:14)

The Ending and Its Interpretations

• The film’s concluding father-son fantasy provides emotional catharsis and ambiguity:

  "The movie starts showing us what could be and what we want to be...You know, we really want Monty...to break free...Dreamlike but real, the color palette is kind of washed..." (Sean, 39:36–40:12)

• Both hosts agree that Monty is, in reality, heading to Otisville, not to an imagined new life out West (49:31).

Notable Quotes & Memorable Moments

• On the film’s energy and mood:

  "This is a story of America in three parts...This is one of the most present tense films ever made." (Sean, 04:09–05:22)

• On 9/11’s repression in media and memory:

  "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." (Amanda, 07:00)

• On the “Fuck You Monologue”:

  "It is filled with hate speech and is very ugly and relies on stereotypes...But it's written from such a knowingness and observation that only comes from truly understanding the place...it's separated from the character..." (Amanda, 17:26)

• On masculinity and friendship:

  "This is really a movie about how men are with each other and how they...kind of don't know how to tell the truth..." (Sean, 23:05)

• On the film’s underappreciated status:

  "I've seen about Prieto, I don't even know how Prieto got on this movie...him colliding with Spike...brings something special out of Spike." (Sean, 43:20)

• On the ending’s emotional power:

  "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...I've never experienced anything like it in a movie." (Amanda, 40:42)

Timestamps for Major Segments

• 01:07 – Episode theme and why 25th Hour is a surprise top-3 pick
• 04:09 – Sean on the film's context, 9/11, and personal resonance
• 06:39 – Amanda on the film’s under-discussed reputation
• 09:59 – Discussion of two iconic scenes: the “Fuck You” monologue & the ending
• 14:14 – Edward Norton’s career and performance
• 16:18 – Analysis of Monty Brogan's character and the monologue
• 20:33 – Scene above Ground Zero and Terrence Blanchard’s score
• 23:47 – The three friends as the male psyche: ego, superego, id
• 31:15 – Exploration of masculinity and predatory male behavior
• 39:28 – The final fantasy sequence and its emotional effect
• 43:20 – Technical credits: Prieto’s cinematography, Blanchard’s score, etc.
• 45:31 – The film’s legacy and missing from major lists
• 47:13 – Other New York and drug dealer movies considered
• 49:31 – Do Amanda & Sean believe Monty goes to Otisville? Yes.

Final Thoughts

• Both hosts passionately endorse 25th Hour as an emotionally searing, technically virtuosic, and thematically dense achievement, lamenting that it's "not celebrated enough" yet confident it will endure as a touchstone for those who love cinema.
• Amanda:

  “I love this film...it's a gut punch in the best way every time, but it's a treat to rewatch it.” (49:39)

• Sean:

  “Was happy to talk to you about it...I feel good about that.” (49:46)

Recommended if You Like...

• Other New York movies: Frances Ha, Uncut Gems, If Beale Street Could Talk, Synecdoche, New York, Requiem for a Dream, Margaret
• Other drug dealer/male friendship movies: Carlito’s Way, Clockers, Boyz n the Hood, Trainspotting, Midnight Express, Once Upon a Time in America, Midnight Cowboy
• Comparison with Lady Bird: “Very, very different movies in every single way. But since we had Lady Bird recently on our list, if you're into that, bring it on over.” (Amanda, 48:59)

Episode Tone

The tone is a blend of nostalgic, analytical, and personally heartfelt, often switching between theoretical discussion and personal anecdotes with spontaneous wit and banter. Both hosts express admiration for Spike Lee’s craft and the film's emotional truth.

For listeners and film fans new to 25th Hour, this episode provides a rich, multidimensional appreciation of why the film matters—and why it remains one of 21st-century cinema's true masterpieces.