The Departed — The Rewatchables Tracker

Back to the movie index

Overall episode#8Source sheet order

Movie year20062000s

Tomatometer91%Critics’ score

Metacritic85View score

Roger Ebert4/4Original star rating

DirectorMartin ScorseseCrime / Drama

FROM THE CONVERSATION

What they said about the movie

A rewatchable, star-driven, flawed-but-thrilling gangster movie that the hosts admire for its pace, performances, quotable lines, and replay value, even while nitpicking plot logic, accents, and a few Scorsese excesses.

Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

In this conversation

Bill Simmons

Chris Ryan

WHY IT WORKS

What made it rewatchable

01Huge star cast where multiple actors seem to think they are the lead, which creates high-energy scenes. Opening minutes
02Memorable dialogue and quotable scenes, especially the cranberry juice/bar fight exchange and Wahlberg's lines. About 16 min
03The movie's flaws and loose plotting make it fun to revisit and debate. About 40 min
04Strong soundtrack and needle drops, especially Dropkick Murphys and Stones usage. About 16 min
05Iconic performances, especially Wahlberg's scene-stealing energy and Leo's intensity. About 32 min

WHAT DID NOT WORK

Their main criticisms

majorNicholson's performance is erratic, with a confusing accent and improvised-feeling excess. About 24 min
moderateThe plot mechanics often do not make sense when examined closely. About 16 min
moderateThe rat on the balcony ending is too on-the-nose. About 40 min
moderateSome Boston accents are weak or inconsistent, especially Martin Sheen's and Nicholson's. About 32 min
minorLeo's behavior in the finale is inconsistent with how smart his character is supposed to be. About 16 min

SCENES THEY KEPT COMING BACK TO

Standout moments

positive

Opening Boston-crime setup and title delay

The title appears late, after extensive setup, which they find unusual but effective.

Opening minutes

Favorite

Dropkick Murphys title sequence and prison workout montage

They love the music and the visual energy of Leo doing jail workouts.

About 16 min

Favorite

Cranberry juice bar scene

The cranberry-juice misunderstanding escalates into a perfect Scorsese bar fight.

About 8 min

mixed

Nicholson's opening monologue on Boston and race

Sets the tone but also feels like an excuse to add extra Jack material.

Opening minutes

critical

Roof meeting and trap setup

They find the rooftop plan implausible and unnecessarily complicated.

About 16 min

Favorite

Nicholson running from the cops

They think Jack's awkward sprint is unexpectedly hilarious.

About 32 min

WHERE THEY DISAGREED

The biggest debates

They agreed About 48 min

Who won the movie: Leo, Damon, Nicholson, or Wahlberg

Bill Simmons
Leans Leo, with Wahlberg as the scene-stealer and Damon also excellent.

Chris Ryan
Leans Leo, while strongly appreciating Damon's sneaky performance.

They partly agreed About 24 min

Whether Nicholson's performance works

Bill Simmons
Mostly no; thinks it is overdone and badly accented.

Chris Ryan
More forgiving in context, but still mixed because the movie's looseness encourages it.

They agreed About 40 min

Whether the movie's flaws help or hurt it

Bill Simmons
Flaws make it more rewatchable because they create questions and conversation.

Chris Ryan
Agrees and says imperfect movies invite repeated viewing.

They agreed About 48 min

Could Leo and Damon have swapped roles

Bill Simmons
Thinks Damon could probably play Costigan but Leo could not play Costello/Colin.

Chris Ryan
Agrees Damon could maybe do Billy/Costigan and Leo could not do Colin.

15 People discussedActors, directors, writers, and producers

favorableMartin ScorseseBill Simmons: Praised as the director who turned the material into a major rewatchable gangster movie, though they note some excesses. Opening minutes favorableLeonardo DiCaprioBill Simmons: Seen as the film's ultimate winner, intense and effective as Costigan, even if his character choices can be shaky. About 8 min favorableMatt DamonBill Simmons: Praised for playing creepy, controlled, sneaky energy well; the hosts think he and Leo could have swapped parts in theory. About 8 min mixedJack NicholsonBill Simmons: Admired for moments and star presence, but criticized heavily for the accent, improvisation, and overall performance. About 8 min very favorableMark WahlbergBill Simmons: Steals scenes with clipped, aggressive comic energy and is repeatedly singled out as a winner. About 16 min favorableAlec BaldwinBill Simmons: Liked for his Boston accent and department-boss energy. About 32 min criticalMartin SheenBill Simmons: Considered weak on the Boston accent and less convincing than some of the other performers. About 32 min mixedVera FarmigaBill Simmons: Her performance starts strong but is said to fade; her character choices are also criticized. About 32 min favorableRay WinstoneBill Simmons: Praised for pulling off the Boston role and owning the cranberry-juice confrontation. About 8 min neutralBrad PittBill Simmons: Mentioned as an early casting possibility and as someone who made a smart producing choice by passing on the Damon role. About 8 min favorableAl PacinoBill Simmons: Used as a hypothetical alternative Costello, with the hosts suggesting he might have been better or at least fun. About 8 min

neutralAnthony AndersonBill Simmons: Mentioned only as the recipient of a memorable Boston-line insult; no real opinion beyond the joke. About 40 min · medium confidence

favorableBill MonahanBill Simmons: His script is described as cool but also ragged and likely improv-heavy. About 24 min

neutralRobbie RobertsonBill Simmons: Referenced as part of Scorsese's music-team approach and soundtrack curation. About 16 min

neutralWhitey BulgerBill Simmons: Used as the real-world model for Costello's menace and Boston-crime-lord persona. About 32 min

14 Conversation takesSpeakers shown only where the transcript identifies them

Bill SimmonsLoved it

The Departed as a star-fest

Argues that the all-star casting is a key pleasure of the movie and that many supporting roles would not be cast that way today.

Opening minutes

Bill SimmonsLoved it

Mark Wahlberg

Thinks Wahlberg is insane in the best way and treats every scene like a showcase.

About 8 min

Bill SimmonsLoved it

Cranberry juice/bar fight

Calls it a perfect scene and one of the movie's great rewatchable moments.

About 8 min

Bill SimmonsDid not like it

Jack Nicholson

Feels Nicholson's performance is the movie's biggest problem because the accent and improvisation go too far.

About 32 min

Bill SimmonsDid not like it

The Departed ending with the rat

Thinks the balcony rat is too much and unnecessary.

About 40 min

Bill SimmonsLiked it

Nicholson running at the end

Finds Nicholson's awkward running one of the funniest moments in the movie.

About 32 min

Bill SimmonsLiked it

The Departed's flaws

Argues the movie is more rewatchable because it has rough edges rather than being perfect.

About 40 min

Chris RyanLiked it

The Departed as a satisfying but weirdly unsatisfying wish-fulfillment movie

Says the movie gives exactly what you want, which can make it oddly unsatisfying at first.

Opening minutes

Chris RyanLoved it

Matt Damon

Thinks Damon is very strong here, especially in the sneaky/creepy register.

About 8 min

Chris RyanLiked it

Leonardo DiCaprio

Believes Leo is excellent and that the role tested whether he could play a street-level Boston undercover cop.

About 8 min

Chris RyanLiked it

Nicholson vs Pacino in Costello role

Would enjoy Pacino in the role and thinks Pacino may fit Costello better than Nicholson did.

About 8 min

Chris RyanLoved it

American ambition and self-division

Offers a long reading of the two leads as metaphors for different American survival strategies.

About 40 min

Chris RyanMixed

Vera Farmiga

Thinks her character should have turned Damon in, even if the romantic dynamic works dramatically.

About 40 min

Chris RyanLoved it

Ray Winstone

Likes his performance and accent work in the film.

About 8 min

5 ThemesThe larger ideas in the discussion

Identity and doubleness

The undercover/counterfeit lives of the two leads mirror each other and drive the film's tension.

Opening minutes

Star power and ensemble hierarchy

The movie works as a competition of famous actors trying to dominate every scene.

Opening minutes

Flawed craft enhances rewatchability

The hosts argue that imperfections, not polish, are part of why the movie remains fun to revisit.

About 40 min

Boston authenticity

Accents, neighborhoods, and local texture are treated as a major part of the movie's appeal and failure points.

About 32 min

Violence and bar-room chaos

Scorsese's recurring bar violence and glass-smashing escalation are treated as a defining style choice.

About 16 min

22 Facts and referencesProduction notes and other movies mentioned

Production note

The film contains 238 swears or variations of the F-word.

Opening minutes

Production note

Leo's part was reportedly first intended for Brad Pitt.

Opening minutes

Production note

The movie won Best Picture in what they call a weak Oscar year.

Opening minutes

Production note

Leo was not nominated for The Departed; the studio pushed Blood Diamond instead.

Opening minutes

Production note

The apartment with the State House view was made up.

About 40 min

Production note

Ray Winstone supposedly turned down Jimmy McNulty.

About 8 min · medium confidence

Mentioned with uncertainty

Nicholson reportedly improvised a dildo-related bit after bringing one to set.

About 8 min · medium confidence

Production note

Wahlberg based his accent/performance on people who arrested him as a youth.

About 24 min

Production note

Scorsese used 'Gimme Shelter' in this film after using it in Goodfellas and Casino.

About 16 min

A Few Good Men

Used as the show template and as a Nicholson comparison point.

Opening minutes

No Country for Old Men

Cited as another movie that feels almost too perfect or exactly satisfying.

Opening minutes

Gangs of New York

Cited as an earlier Scorsese/LA-NY movie event that felt like a big deal.

Opening minutes

Goodfellas

Used as the benchmark for Scorsese gangster energy and soundtrack choices.

About 16 min

Casino

Mentioned as another Scorsese film that uses 'Gimme Shelter.'

About 16 min

The Shining

Used in a joke about when Nicholson may last have run on screen.

About 32 min

Mystic River

Referenced while discussing Boston drama and Sean Penn casting hypotheticals.

About 32 min

Heat

Used to contrast careful craft with this film's looser feeling.

About 48 min

Silence of the Lambs

Used to explain how a colorful villain can make a thriller more rewatchable.

About 48 min

Infernal Affairs

Named as the original film this was remade from.

About 48 min

Blood Diamond

Discussed as the vehicle the studio pushed for Leo's Oscar campaign instead of The Departed.

Opening minutes

Glengarry Glen Ross

Referenced in comparing Wahlberg's dressing-down of Leo to the Alec Baldwin speech energy.

About 56 min

The Wire

Mentioned because Ray Winstone reportedly turned down Jimmy McNulty.

About 8 min

10 Running jokes and short linesRecurring bits captured from the conversation

Scorsese bar-violence montage

They repeatedly joke that Scorsese movies inevitably involve someone being hit over the head in a bar.

About 8 min

The accent scoreboard

A running gag weighs which actors did or did not nail Boston accents.

About 32 min

Gimme Shelter overload

They joke about Scorsese overusing the Rolling Stones song.

About 16 min

Nicholson running

They keep revisiting how absurdly Nicholson runs in the finale.

About 32 min

You're the other guy

They linger on the movie's best insult exchange and say it should be reused in the office.

About 40 min

Speaker not identified

“You all are, act accordingly.”

Opening minutes

Speaker not identified

“Cranberry juice, that's a natural diuretic.”

About 8 min

Speaker not identified

“Maybe, maybe not. Maybe fuck yourself.”

About 40 min

Speaker not identified

“How's your mother? She's on her way out.”

Opening minutes

Speaker not identified

“Who the fuck are you? I'm the guy”

About 40 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where The 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

2 voices on this episode

Bill SimmonsThe Rewatchables

Chris RyanThe Rewatchables

REWATCH FAVS

One of your favorites?

Upvote it for the live listener ranking.

YOUR PROGRESS

Save this one to your tracker

KEEP LISTENING

Hear the full conversation

Play the episode directly from the official feed, open it on Spotify, or save it to your private Listen Later playlist.

Play episode Find on Spotify