The hosts argue that The Departed is a hyper-rewatchable, chaotic-but-deliberate Scorsese crime movie that plays like an Irish-American gangster greatest-hits package. They praise its speed, star power, editing, shock deaths, and recurring comic set pieces, while also calling out some sloppy plotting, dated elements, and a few overly broad or goofy choices.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections
01It moves like a 'zipline' movie: fast, propulsive, and never dull, with a conclusion it hurtles toward. About 8 min
02It works as a loopable background watch because individual scenes remain engaging even out of order. About 8 min
03The movie is packed with memorable star turns from Leo, Damon, Nicholson, and Wahlberg. About 8 min
04The second half keeps escalating, so the movie becomes more rewatchable as it goes on. About 8 min
05Its scene construction is full of quotable confrontations and violent shocks. About 32 min
WHAT DID NOT WORK
Their main criticisms
moderateThe plotting is messy and occasionally confusing, especially around the microprocessors/FBI material and some cross-cutting choices. About 8 min
moderateNicholson's performance is considered broad and uneven, with some improvisational-feeling detours. About 8 min
minorThe rat ending is divisive and feels either intentional maximalism or an overly literal thematic button. About 40 min
minorSeveral Boston details feel inauthentic or anachronistic, including the Combat Zone, accents, and locations. About 40 min
minorThe opening montage/background material is seen as unnecessary for a film already running long. About 40 min
SCENES THEY KEPT COMING BACK TO
Standout moments
Favorite
Wahlberg/Dignam insults Leo
Dignam hammers Costigan with insults and identity questions, establishing the movie's comic aggression.
About 32 min Favorite
Cranberry juice scene
Ray Winstone's cranberry-juice order becomes a perfect comic threat scene and a Boston bar moment.
About 32 min Favorite
Costello's introduction at the bar
Nicholson's entrance is treated like Satan walking into the room, with a great slow-burn introduction.
About 40 min Favorite
Driving range with Baldwin
Baldwin's marriage-and-career monologue is praised as one of the movie's funniest scenes.
About 40 min Favorite
Porn theater / Nicholson rat scene
The porn-theater sequence and the rat reveal are singled out as weird, memorable, and highly rewatchable.
About 40 min Favorite
Sheen's death
Queenan's fall is described as a shocking, beautifully staged death that stunned theater audiences.
About 48 min Favorite
Triple-cross / elevator ending
The final rooftop-to-elevator stretch is considered the best-executed and most suspenseful sequence.
About 48 min Favorite
Leo shot on the staircase
Costigan's sudden death is treated as the movie's most shocking theater moment.
About 48 min
WHERE THEY DISAGREED
The biggest debates
They partly agreed About 24 min
Nicholson's performance: necessary or too broad?
Bill Simmons
The movie needs a famous, imposing older star here, but Nicholson is not actually giving a great performance.
Chris Ryan
Nicholson is entertaining and iconically chaotic even if it is not a subtle turn.
No final agreement About 56 min
Who won the movie: Scorsese or DiCaprio?
Sean Fennessey
Scorsese won because the film cemented his commercial and awards legacy.
Bill Simmons
DiCaprio won because the performance is the movie's emotional engine and career-defining proof point.
They left it as a friendly argument About 48 min
Should Jack Nicholson have worn a Red Sox hat?
Bill Simmons
Yes, refusing the hat is absurd for this Boston movie.
Chris Ryan
The issue is less important than the performance and the movie's broader energy.
They partly agreed About 48 min
Would the movie improve with alternate casting?
Bill Simmons
Several alternatives could have worked, including Hackman for Nicholson and possibly different actors for Dignam.
Chris Ryan
The current cast mostly works because the performances are so specific to the movie's energy.
11 People discussedActors, directors, writers, and producers
Treats the ending sequence as the best-executed stretch of the movie, with multiple shocking turns.
About 48 min
5 ThemesThe larger ideas in the discussion
Identity and performance
The hosts read the movie as a study of two people living opposite versions of identity: Costigan as raw vulnerability and Sullivan as constructed performance.
About 32 min
Catholic guilt and Irishness
They frame the movie as Scorsese's Irish-Catholic take on gangster guilt, family, and melancholy.
Opening minutes
Chaos versus control
The film is described as simultaneously intricately constructed and chaotically edited, which they think is part of its appeal.
About 8 min
Makeup Oscar / career turning point
They treat the film as the movie that finally canonized Scorsese as a major commercial and awards success.
About 16 min
Comedy inside crime
The hosts repeatedly argue that the movie is funniest when the characters are insulting each other and that the comedy is a key part of its rewatchability.
Opening minutes
23 Facts and referencesProduction notes and other movies mentioned
Production note
The episode repeatedly notes that the film won Best Picture, Director, Screenplay, and Editing.
About 16 min
Production note
The hosts say the movie's Oscar year was unusually weak and list other nominees they preferred.
About 16 min
Production note
They claim the movie's production and release helped redefine Scorsese as a filmmaker who could command major commercial budgets.
About 16 min
Production note
Bill says the X motifs in the film mark people who are about to die.
About 8 min
Production note
The hosts say the movie uses music aggressively and repeatedly, especially 'Gimme Shelter.'
About 40 min
Production note
They note that the movie was shot partly in Boston and partly in New York, which contributes to some geographic inaccuracies.
About 40 min
Production note
Bill says Whitey Bulger is a layup for Hollywood, and that prior adaptations have botched him.
About 32 min
Mentioned with uncertainty
They joke that one of the cast what-ifs could have been a 'Dignam show' with Mark Wahlberg.
About 48 min · medium confidence
The Godfather
Used as the comparison point for the 'Irish Godfather' framing.
Opening minutes
Infernal Affairs
Cited as the 2002 source film that The Departed remakes.
About 40 min
Goodfellas
Used as a Scorsese comparator and as the film that should have won the Oscar decades earlier.
About 16 min
A Few Good Men
Referenced as an earlier Rewatchables benchmark for rewatchability.
About 8 min
The Town
Mentioned as a comparison point for Boston crime movies and for a past Bill/Chris debate.
Opening minutes
Gangs of New York
Cited as Scorsese's prior prestige project before The Departed.
About 16 min
The Aviator
Mentioned as another awards-oriented Scorsese film before The Departed.
About 16 min
Black Mass
Used as an example of Hollywood botching Whitey Bulger material.
About 32 min
Blood Diamond
Referenced because DiCaprio was nominated for it instead of The Departed.
About 24 min
Children of Men
Discussed as a movie that should have been in the 2006 Oscar field instead of some nominees.
About 16 min
Little Miss Sunshine
Cited as one of the weaker Best Picture nominees from 2006.
About 16 min
The Queen
Cited as another weak Best Picture nominee from 2006.
About 16 min
Borat
Named as a more deserving 2006 Oscar contender.
About 16 min
The Shining
Used in a Nicholson death-scene mini-ranking.
About 48 min
Psycho
Referenced in the trivia about the shower-scene shot pattern used during the shower listening scene.
About 56 min
12 Running jokes and short linesRecurring bits captured from the conversation
Rusillo/The Town dig
They repeatedly joke that Rusillo loves The Town more and missed the recording because the podcast was supposed to revolve around his take.
Opening minutes
Scorsese greatest-hits / songs restart
They joke that the movie feels like Scorsese forgot he already used certain songs or motifs.
About 8 min
Dignam insults
Repeated quoting of Wahlberg's verbal attacks becomes a recurring comic bit.
About 32 min
Cranberry juice / natural diuretic
Ray Winstone's cranberry juice order and the line about diuretics keep resurfacing as a joke.
About 32 min
Red Sox hat outrage
Bill keeps insisting Nicholson's refusal to wear a Red Sox hat is an outrageous Boston-movie choice.
About 48 min
Combat Zone nostalgia
Bill and Chris riff on Boston's old Combat Zone and how the film's porn-theater material is out of date.
About 40 min
Michael Mann 're-reheat'
Bill jokes about doing a future heat-style rewatch with Michael Mann, and the others play along.
About 56 min
Sean Fennessey
“It's the Irish Godfather.”
Opening minutes
Bill Simmons
“What's a lace curtain motherfucker like you”
About 32 min
Bill Simmons
“The guy who does his job.”
About 40 min
Bill Simmons
“I got this rat, this annoying, teething rat.”
About 40 min
Bill Simmons
“Two weeks with pay!”
About 48 min
MAKE IT A MOVIE NIGHT
Where to watch
UNITED STATES
Checking where The Re-Departed is available…
WHAT TO WATCH NEXT
Movies to watch before and after.
Three movies to watch before The Departed, and three to watch next.
Finding six movies…Three to watch first and three to watch next.
ON THE MIC
3 voices on this episode
Bill SimmonsThe Rewatchables
Chris RyanThe Rewatchables
Sean FennesseyThe Rewatchables
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