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The Rewatchables · September 2, 2025

American Gangster

host Bill Simmons host Chris Ryan host Van Lathan producer Craig Horlbeck

Casting what-if: James Gandolfini as Trupo
Weakest link: The movie’s extensive historical fabrication
Needle drop: Public Enemy’s “Can’t Truss It” at Frank’s release

All 34 categories

Who won the movie Denzel Washington
Just one Oscar Arthur Max’s art direction
Dion Waiters Award Cuba Gooding Jr.
“That Guy” Award Roger Guenveur Smith

The Stephen A. Smith Hottest Take Award · 1:30:26

Josh Brolin’s post-film career and alternate-director arguments drive three hot takes

Chris Ryan: Josh Brolin is argued to have had the best post-American Gangster career in the cast

Van Lathan: Ridley Scott is argued to have prevented the material from becoming a classic

The Coach Finstock Award for Best Life Lesson · 1:56:06

Quitting while ahead is not the same as quitting

Bill Simmons: “Quitting while you’re ahead is not the same as quitting” is selected by two participants

The film

American Gangster (2007)

Directed by Ridley Scott · Crime

157 minutes

IMDb Find on JustWatch Find on Rotten Tomatoes

Cast

Selected cast credits · Film reference

Denzel Washington Frank Lucas

Russell Crowe Richie Roberts

Josh Brolin Detective Nick Trupo

Chiwetel Ejiofor Huey Lucas

Ruby Dee Mahalee Lucas

Lymari Nadal Eva

Armand Assante Dominic Cattano

Carla Gugino Laurie Roberts

Cuba Gooding Jr. Nicky Barnes

Ted Levine Lou Toback

Idris Elba Tango

John Hawkes Freddie Spearman

John Ortiz Javier J. Rivera

RZA Moses Jones

Roger Guenveur Smith Nate

Yul Vazquez Alfonse Abruzzo

Joe Morton Charlie Williams

Common Turner Lucas

Tip Harris Stevie Lucas

Ritchie Coster Joey Sadano

Jon Polito Rossi

Kevin Corrigan Campizi

Malcolm Goodwin Jimmy Zee

Ric Young Khun Sa

Roger Bart U.S. Attorney

KaDee Strickland Richie's attorney

Ruben Santiago-Hudson Doc

Norman Reedus Detective Norman Reilly

Melissia Hill Redtop

Robert Funaro McCann

Clarence Williams III Bumpy Johnson

Everything from the episode

In the order the hosts got to it. Open a row for the discussion.

1:33:55

Casting What-Ifs

James Gandolfini as Trupo; Ray Liotta; Brad Pitt; Eddie Murphy

In the discussion (3)

Approx. transcript time · 01:33:55Read transcript

James Gandolfini reportedly declined Trupo and is judged an excellent hypothetical choice — Bill Simmons
Ray Liotta is mentioned as an earlier Richie possibility — Chris Ryan
Brad Pitt and Eddie Murphy are mentioned as having had some connection to development — Bill Simmons

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1:36:42

Recasting Couch

Ray Liotta and Eva Mendes

In the discussion (3)

Approx. transcript time · 01:36:42Read transcript

Ray Liotta is proposed for Dominic Cattano — Bill Simmons
Ray Liotta as Trupo or Richie is preferred over casting him as the mob boss — Chris Ryan
Eva Mendes is proposed as Frank’s wife

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1:38:11

Half-Assed Internet Research

Budget penalties, gifts, real-world family connections, locations, and a Godfather Part III idea

In the discussion (6)

Approx. transcript time · 01:38:11Read transcript

Brian Grazer and Ridley Scott reportedly returned three million dollars after overrunning the budget — Bill Simmons
The BET series American Gangster is noted as predating the movie — Bill Simmons
Russell Crowe reportedly gave RZA a mint 1961 Gretsch guitar and they remained friends — Bill Simmons
Frank Lucas’s real driver is identified as Sean Combs’s father, who was killed when Combs was two — Chris Ryan
The production used parts of upper Manhattan that could still pass for 1970s New York — Chris Ryan
Francis Ford Coppola reportedly considered a Frank Lucas-like character for The Godfather Part III — Chris Ryan

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1:46:44

Picking Nits

Frank’s market position, lack of consequences, unclear chronology, family awareness, and fabricated epilogue

In the discussion (8)

Approx. transcript time · 01:46:44Read transcript

Frank’s superior direct supply should have let him eliminate Harlem competition — Bill Simmons
Territory and distribution relationships are offered as constraints on expansion
Frank faces no repercussions for shooting Tango in public — Bill Simmons
Harlem loyalty is offered as an explanation for the silence — Bill Simmons
Woody Allen and Diane Keaton are shown together before their real relationship and before Keaton was well known — Bill Simmons
The chronology is too unclear about whether scenes are weeks or years apart — Chris Ryan
Frank’s mother knowing he sells drugs is criticized as disconnected from the movie’s reality — Chris Ryan
The closing-title claims are mocked for extending the film’s fabrications — Bill Simmons

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1:51:57

Probably Unanswerable Questions

Absent actors, Denzel’s persona, ideal length, Trupo, Frank’s wife, and Stevie’s Yankees path

In the discussion (8)

Approx. transcript time · 01:51:57Read transcript

How Mark Ruffalo missed the large ensemble is asked
Whether this performance created Jay Pharoah’s Denzel Washington impression is asked — Bill Simmons
The maximum acceptable length is debated; one participant would watch a six-hour event
More Vietnam, Jake, Stevie, and Frank-fall material is requested
Trupo’s home life and golf club are questioned — Van Lathan
Whether Frank’s wife set him up by insisting on the fur coat is debated
The unexplained fake beard is raised as evidence of missing connective material
Whether Stevie could plausibly go from the street to the Yankees in 1974 is questioned — Bill Simmons

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1:56:06

Best Double Feature

The French Connection; Blow

In the discussion (4)

Approx. transcript time · 01:56:06Read transcript

The French Connection is selected as the best pairing and described as a narrative precursor
Virtuosity is proposed for an earlier Crow-Washington pairing — Chris Ryan
Ricochet prompts a tangent but is not selected
Blow is added as another preferred pairing — Bill Simmons

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