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The Departed

151 minutes

Cast

Selected cast credits · Film reference

Leonardo DiCaprio Trooper William "Billy" Costigan Jr
Matt Damon Staff Sergeant Colin Sullivan
Jack Nicholson Francis "Frank" Costello
Mark Wahlberg Staff Sergeant Sean Dignam
Martin Sheen Captain Oliver "Charlie" Queenan
Ray Winstone Arnold "Frenchie" French
Vera Farmiga Dr. Madolyn Madden
Alec Baldwin Captain George Ellerby
Anthony Anderson Trooper Brown
Kevin Corrigan Sean Costigan

The Departed | The Rewatchables

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Most Rewatchable Scene

Wahlberg and Baldwin grilling DiCaprio; driving range scene; rooftop triple cross and elevator; Frank meets Billy to 'Let It Loose'; Queenan's fall and Dignam quitting; French and Frank's 'reliable' talk; Madeline and Billy's first session and Comfortably Numb scene

In the discussion (18)
Approx. transcript time · 00:36:26Read transcript
  • The first pod handled this category loosely; this time they are doing it correctly, likened to the third Seinfeld plot when they had figured out how to incorporate Elaine, but not really.
  • First pick: Walberg's Dignam, with Baldwin, grilling Leo ("lace curtain motherfucker", "double kid", different accents), treated as one long scene that could be watched on YouTube for hours.
  • Walberg is really good here even if he dials it up; it is called the second best use of him after Dirk Diggler, and his character makes no sense, which the movie turns into a trick that pays off in the last shot; James Badge Dale's character works similarly.
  • The cranberry juice scene, missing from the last episode: Ray Winstone's "guys you can hit" monologue, the bar patron's "natural diuretic" line, and the later Nicholson callback; the sarcastic reaction is called exactly what would happen in a Boston bar.
  • Borderline pick: Damon's first date with Vera, well written and acted.
  • Leo meets Costello in the bar: a favorite character introduction via the two middle-aged ladies and "Mr. French", like Satan or Michael Myers arriving, then the back-room scene where the undercover cop's pushback leaves Costello wondering what is wrong with this kid.
  • The "spilled guineas" line is called a weird line that got greenlit and the first 35 minutes pretty racist.
  • DiCaprio called filming a one-on-one scene with Jack one of the most memorable moments of his life; it is unclear whether he meant the bar scene or the table scene with the drawing and rat noises, which feels improvised.
  • The Chinese surveillance scene, picked for Walberg's "I'm the guy who does his job. You must be the other guy," called one of the great movie lines, plus Baldwin fired up about the Patriot Act as a snapshot of the time.
  • The driving range scene: Baldwin's theory on marriage and Damon's "working overtime"; the golf swing is bad; the scene is nearly shot for shot from Infernal Affairs, which had no humor.
  • The porn theater scene is well constructed, with Nicholson's dildo, leading into the "I got this rat" scene.
  • 344 Washington: Sheen falling to his death was shocking in the theater; the van drives over the body and blood spatters Leo; it leads straight to Walberg quitting ("two weeks with pay") and Boggs as Delahunt.
  • Also listed: Damon calling a dead man's phone, Costello's death scene with Jack running, Mr. French killing himself just before the car blows up, and Leo versus Damon.
  • Adds the random French and Frank scene about who is reliable, with the cutaway to Frank murdering his wife called anachronistic. — Chris Ryan
  • Adds two Madeline and Billy scenes: the first session ("two pills... give me a bottle of scotch and a handgun") and the Comfortably Numb sex scene, one of the very few good love scenes in a Scorsese movie. — Chris Ryan
  • Another answer: the movie is most fun when Wahlberg or Baldwin gives someone shit, especially the first Walberg sequence with Leo and Baldwin on the driving range; the rooftop confrontation, triple cross and elevator is the best executed sequence.
  • Favorite: Frank meets Billy with the Stones' "Let It Loose" playing; the most enjoyed combination is Sheen falling to his death followed by Walberg quitting.
  • The triple shooting is among the best action Scorsese has shot, shock after shock from Anthony Anderson to Barrigan, forcing viewers to reprocess Barrigan as a Costello mole; seeing it next to Tarantino would be even more fun.

What’s Aged the Best?

Leo versus Damon; Damon's villain performance; Damon's Boston accent; Damon's contempt for firemen; Baldwin and Wahlberg running SIU; Baldwin's 'go fuck yourself'; Nicholson's death scene; Scorsese's highball-glass record; the 'black guy in Boston' line

In the discussion (10)
Approx. transcript time · 00:52:28Read transcript
  • Leo versus Damon as generational rivals, like LeBron and Durant, with Walberg compared to James Hardin and then Anthony Davis; the movie catches both at their peaks.
  • Leo and Damon reportedly barely saw each other during production, shooting nights and days respectively, like Heat.
  • Damon's performance is called underrated: an effortless, unlikable, insecure villain; many of his best roles (School Ties, Ripley, The Informant, early Good Will Hunting) are good jerks.
  • Damon versus Walberg for the goat Boston accent in a movie, and Damon wins: here it is the accent of someone trying to hide it while climbing, slipping out in the wrong spots; one participant says he knows nothing about the Boston accent.
  • Damon's real contempt for firemen, and the credits arriving 18 minutes in.
  • Baldwin and Wahlberg running SIU with no HR department; questions about why it is state troopers rather than Boston PD, perhaps speaking to trooper incompetence; Baldwin's "go fuck yourself" is great.
  • The Nicholson death scene is really good, prompting an impromptu best Nicholson death scene: Cuckoo's Nest, The Shining and Batman join The Departed as a Mount Rushmore; Witches of Eastwick is pitched; The Shining maze death is preferred by one participant.
  • His shirt reading Irish in the death scene; Nicholson's own choices (the dildo, the cocaine, the opera) suggest he had carte blanche.
  • Scorsese officially breaks the record for characters hitting another character over the head with a highball glass, and no bar scene ever works out in a Scorsese movie.
  • The line to Anthony Anderson that as a black guy in Boston he does not need help to be completely fucked is called a subtle, smart Boston touch.

What’s Aged the Worst?

Opening background montage; the final rat; Gimme Shelter reuse; blind pocket texting; microprocessors plot device; cocaine opera scene; bad Boston accents; Nicholson's race monologue, dildo and Red Sox hat refusal; confusing final shootout; New York standing in for Boston; nonexistent State House view

In the discussion (19)
Approx. transcript time · 00:58:30Read transcript
  • The opening background montage is held for this category: it does not work, feels like a different movie, and could be cut from a two-and-a-half-hour film since a later line does the work.
  • Nicholson is saved for last; Nicholson running has aged both best and worst.
  • The rat is disliked, and the body on the floor in the reverse shot is not Damon; nobody told Scorsese no in 2006, likened to their own Miami Vice pod.
  • A requested defense of the rat, not fully believed: in a maximalist movie it is the final maximalist note, meaning corruption rises to the top and betrayal lives on in institutions; the reply is that a cool crime movie does not need a grand statement.
  • Flip phones as a central character are listed, but also called a nice time capsule.
  • Walberg's hair: joking speculation that this was the last movie before he found a hair guy, with a Tom Brady comparison, explicitly labeled speculation; a defense of Irish hair becoming a bouffant applies to the character, not Walberg.
  • Gimme Shelter used a third time after Goodfellas and Casino, looped three times here; it is defended as an intentional sonic-barrage motif as in Wolf, but his earlier uses were more precise and the song became a cliche and crutch.
  • Damon texting blind in his pocket on T9 would never happen with an iPhone.
  • The microprocessors plot device is questioned; it should have been a drugs and guns movie, though it may exist to justify FBI interest, as in early The Wire.
  • The cocaine opera scene is bonkers with no explanation, possibly Nicholson wanting to have fun, or showing Costello as Satan and a pure hedonist.
  • Bad Boston accents: Leo is okay, Baldwin is a Long Island-Boston hybrid; the bad ones include Vera, who abandons hers after an hour, and Martin Sheen, whose lifer character needed it.
  • Nicholson items: the race monologue should have been cut, the porn theater dildo is inexplicable, and he refused to wear a Red Sox hat and banned them on set in a Boston gangster movie despite killing people onscreen.
  • Whether Whitey Bulger wore a Red Sox hat is questioned; Nicholson may wear a Yankee hat in one scene; a joke that someone in Costello's crew would shoot him over it.
  • Found a photo of Whitey Bulger wearing a Red Sox hat. — Craig Horlbeck
  • The shootout that kills Costello is spatially confusing, and some cutting misfires, such as blood exploding from Sheen before he hits the ground.
  • It is not really Boston: they shot only a couple weeks there, and the Chinatown chase is obviously New York.
  • Costello's scheme to confirm Billy is not the rat is unimpressive, a plot flaw.
  • John Lennon's "Well Well Well" plays and then Nicholson opens a John Lennon speech, called ridiculous though entertaining.
  • The State House view from the condo in the last shot does not exist, since Beacon Hill is surrounded by buildings and trees; tied to an old Blown Away complaint about bastardized Boston geography.
In the discussion (4)
Approx. transcript time · 01:21:51Read transcript
  • New this time; nominees include Boggs a.k.a. Delahunt (Mark Ralston), Kevin Corrigan (a Chris Ryan all-time favorite), Ray Winstone, Fitsy (David O'Hara) and James Badge Deo.
  • Ray Winstone is ruled out as essentially a fifth lead and not Irish; one participant would rather save Kevin Corrigan for Dion.
  • A deep-cut nominee: J.C. McKenzie as Damon's realtor.
  • The winner is Boggs, an incredible that guy.

Apex Mountain

Dropkick Murphys; Van Morrison's live 'Comfortably Numb'; Kevin Corrigan as cop-magnet cousin

In the discussion (10)
Approx. transcript time · 01:36:15Read transcript
  • Leo has a case, with this and Blood Diamond in the same year and merging critical acclaim with blockbusters (Shutter Island, Wolf of Wall Street).
  • Matt Damon, no; Scorsese, no, although a case was made for a career apex.
  • The Dropkick Murphys are a yes: Papelbon used "Shipping Up to Boston" as entrance music and it became the Red Sox song; the Bosstones missed with "The Impression That I Get".
  • Jack Nicholson, no; Mark Wahlberg, no.
  • "Comfortably Numb" as a song had bigger moments on its original release, but this Van Morrison live-album version is a yes.
  • After not knowing "Comfortably Numb", quizzed to name a Pink Floyd song and answers The Wall. — Craig Horlbeck
  • Combat Zone porn theaters are raised, but the area had been cleaned up years before 2006, making them an anachronism; memories of the Combat Zone and a porn theater near the Boston Garden.
  • Alec Baldwin, no (30 Rock); Southie and extended Boston, no, done better; Vera, no (Conjuring, Up in the Air).
  • Kevin Corrigan is the apex mountain of being a cop-magnet cousin; the back porch view recalls Charlestown.
  • The "Thief's Theme" drive is called a rare great Scorsese hip-hop moment that should have been put in Apex.

What Piece of Memorabilia Would You Want From This Movie?

Damon's flip phone; briefcase of microprocessors; Damon's American flag hat

In the discussion (1)
Approx. transcript time · 01:51:46Read transcript
  • Picks: the Damon flip phone, a briefcase full of microprocessors, and the Damon American flag hat, perhaps an ode to the Combat Zone or the Patriot Act.
In the discussion (8)
Approx. transcript time · 01:52:13Read transcript
  • DeCaprio is proposed, as last time, followed by "Yeah. I agree."
  • Martin Scorsese, who won Best Director at the Academy Awards. — Sean Fennessey
  • Pushback: the question is who won the movie, not who made the best movie, and Leo wins it.
  • The Scorsese case: a $300 million movie, the two biggest movie stars playing opposite each other, and the long-awaited Best Picture and Best Director.
  • Still Leo: one of the most important actors of a lifetime, who proved in two and a half hours that he could do anything.
  • Thought experiment: Leo needed this movie for his stretch but was already Leo; without it Scorsese likely never wins Best Picture or Director and becomes Charles Barkley.
  • Sides with Sean's pick of Scorsese. — Craig Horlbeck
  • The tally is tied two to two; the Scorsese case is seen from a career standpoint, but Leo wins the movie; both did it, and there are many winners.
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Leonardo DiCaprio

The Departed | The Rewatchables

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Apex Mountain

No affirmative selection

In the discussion (1)
Approx. transcript time · 00:04:33Read transcript
  • The four stars’1997 achievements are contrasted with this film, and Apex Mountain is declined as nobody’s apex.

Most Rewatchable Scene

The opening briefing; the rooftop meeting and death

In the discussion (7)
Approx. transcript time · 00:09:06Read transcript
  • The Nicholson–DiCaprio confrontation repeatedly asking whether he is still a cop is nominated.
  • Queenan’s rooftop death and body fall are nominated.
  • Wahlberg killing Matt Damon at the end is nominated.
  • Sullivan calling Costigan on Queenan’s dead phone is nominated.
  • Costigan’s sudden elevator death is nominated and remembered for making the theater gasp.
  • The opening briefing with DiCaprio, Baldwin and Wahlberg is explicitly selected as most rewatchable.
  • The rooftop meeting with Queenan is described as the part one host always watches, including Queenan’s fall and the reaction afterward.

Casting What-Ifs

Reported or imagined alternatives: Brad Pitt, Ray Liotta, Denis Leary, Pacino, De Niro, Gibson, and RZA; uncertain Nicholson improvisation stories

In the discussion (8)
Approx. transcript time · 00:14:38Read transcript
  • Brad Pitt was reportedly set for the Damon part, dropped out, and produced instead.
  • Ray Leota was reportedly set for Dignam but could not do it.
  • Denis Leary was the next reported Dignam possibility and also could not do it.
  • Al Pacino was the first reported Costello choice and is debated as an alternate.
  • Robert De Niro reportedly declined Queenan to make The Good Shepherd.
  • Mel Gibson reportedly could not play the Alec Baldwin part because he was filming Apocalypto.
  • RZA was reportedly offered the Anthony Anderson role.
  • Nicholson’s proposed prostitute scene and retained dildo improvisation are presented with explicit uncertainty.

What’s Aged the Best?

DiCaprio versus Damon, the delayed title, Baldwin and Wahlberg’s department, the cranberry-juice scene, Costello’s death, Dropkick Murphys, and contemporary Boston sports links

In the discussion (8)
Approx. transcript time · 00:17:36Read transcript
  • The contrast between DiCaprio and Damon is praised.
  • The title arriving about eighteen minutes into the movie is praised.
  • Costigan’s jail workout is part of the delayed-title sequence.
  • Alec Baldwin and Mark Wahlberg running an internal-affairs-on-internal-affairs department is praised.
  • The cranberry-juice confrontation is praised as a perfect scene.
  • Costello’s death is nominated.
  • Dropkick Murphys entering with the title is praised.
  • The Dropkick Murphys cue is linked to the closer transcribed Papoban and the Red Sox era.

What’s Aged the Worst?

T9 pocket texting

In the discussion (7)
Approx. transcript time · 00:21:24Read transcript
  • Nicholson’s entire performance is nominated as aged worst.
  • Mark Wahlberg’s hair is criticized.
  • Costigan’s panic and handling of the Citizens Bank envelope are questioned against his established intelligence.
  • Costigan’s plan to trap Matt Damon’s character on the same roof where Queenan died is questioned.
  • Damon sending a complicated T9 text in his pocket is the explicit winner, with agreement, and is considered implausible and dated.
  • The Chinese-microchip subplot is dismissed as confusing.
  • Scorsese’s third use of “Gimme Shelter” is criticized as overuse despite other strong Stones choices.

The Joey Pants “That Guy” Award

Mark Rolston and Kevin Corrigan remain split choices after nominees Ray Winstone, James Badge Dale, Anthony Anderson, and David O’Hara.

In the discussion (7)
Approx. transcript time · 00:25:32Read transcript
  • Ray Winstone is nominated as Mr. French, with debate over whether the role should have gone to an even bigger actor.
  • James Badge Dale is nominated as Trooper Barrigan.
  • Anthony Anderson is nominated as a 2006 That Guy who later became a name.
  • David O'Hara is nominated as Fitsy.
  • Mark Rostin is one host’s winner because of his Shawshank identity as Boggs.
  • Kevin Corrigan is the other host’s winner as the perfect Costigan cousin.
  • The hosts end by agreeing to disagree rather than naming co-winners.

Half-Assed Internet Research

Winstone and Nicholson’s friction, Nicholson’s Red Sox/Celtics refusal, DiCaprio’s project choice, accent coach Jay Giannone, profanity, and Wahlberg drawing on people who arrested him

In the discussion (6)
Approx. transcript time · 00:28:40Read transcript
  • Ray Winstone reportedly said he and Nicholson did not get along during filming.
  • Nicholson reportedly refused a Red Sox hat and banned Celtics hats on set.
  • DiCaprio left The Good Shepherd to make The Departed.
  • DiCaprio’s Boston accent coach is named as Jay Giannone.
  • The film is reported to use “fuck” or derivatives 238 times.
  • Wahlberg reportedly based Dignam on a compilation of people who arrested him as a youth.

Unintentional Comedy Award

Nicholson running

In the discussion (5)
Approx. transcript time · 00:35:46Read transcript
  • Scorsese’s repeated “Gimme Shelter” use is nominated through jokes about placing the song over other films.
  • Costello’s dildo is nominated.
  • The flip phones are nominated as funny in retrospect.
  • Sullivan’s impotence material and Baldwin’s “mine’s working overtime” line are nominated.
  • Nicholson’s three-second run is selected as the funniest moment.

Picking Nits

Costigan accepting undercover erasure, the impossible statehouse view, the central romance, Madolyn’s inaction, an intentionally forgettable killer, Queenan missing Sullivan, and the literal final rat

In the discussion (7)
Approx. transcript time · 00:38:32Read transcript
  • Costigan’s willingness to accept the undercover assignment and identity erasure is questioned.
  • Damon’s character’s impossible statehouse apartment view is questioned.
  • Whether Costigan and the doctor would get together is questioned and then accepted through a larger reading of Costigan and Damon’s character as opposing ways of living.
  • the doctor not turning Damon’s character in after Costigan’s death is questioned.
  • Casting a forgettable actor as Costigan’s killer is debated against using a more famous face that would telegraph his purpose.
  • Queenan’s failure to suspect Damon’s character despite obvious suspicious behavior is questioned.
  • The literal rat at the end is criticized as an overly explicit symbol, then partly defended as a closing bow.

The Neil McCauley “A Book about Metals” Award for Best Line from the Movie

The job/other-guy exchange and other insults are nominated; Two weeks with pay receives explicit favorite status, and the prescription/scotch retort is the separate answer.

In the discussion (6)
Approx. transcript time · 00:45:23Read transcript
  • The cranberry-juice exchange is nominated.
  • The guy who does his job / the other guy exchange is nominated without adding a character attribution absent from the cited segment.
  • Dignam’s “maybe, maybe not, maybe fuck yourself” and dead-phone lines are nominated.
  • Costello’s environment line and other aphorisms are nominated.
  • The world needs plenty of bartenders is nominated; the immediately following Two weeks with pay receives the explicit favorite status.
  • Costigan’s request for two pills and joke about scotch and a handgun is another favorite.
In the discussion (4)
Approx. transcript time · 00:47:14Read transcript
  • The choice is Leo, followed by agreement on Leo winning the movie.
  • Mark Wahlberg is described as overwhelming on early viewings before the preference shifts to DiCaprio.
  • Matt Damon is praised for his creep performance and as the structural counterpart.
  • Nicholson is said to lose the movie because of excess.
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Leonardo DiCaprio

More from the conversation

The costly all-star ensemble is praised against a newer model of one or two expensive leads and cheaper supporting casts. The speakers speculate about salary-heavy budgeting and New York tax-credit filming; each star appears determined to dominate limited screen time.
Approx. transcript time · 00:03:34Read transcript
The1997 career peaks of Wahlberg, Damon, DiCaprio and Nicholson are contrasted with2006: Damon is established in franchises, DiCaprio is proving range after Titanic, and Nicholson is entering an unusual late-career villain role.
Approx. transcript time · 00:04:33Read transcript
Scorsese’s Oscar win is weighed against earlier missed opportunities and the competing2006 nominees; the speakers accept The Departed as the best choice while noting a makeup-award feeling. DiCaprio’s Blood Diamond campaign instead of this film is criticized.
Approx. transcript time · 00:06:55Read transcript
The Departed, Wolf and Django are named as three favorite DiCaprio performances without an internal ranking; The Revenant is characterized as a physically demanding awards performance.
Approx. transcript time · 00:08:49Read transcript
The panel ranks seven Boston accents into yes/maybe/no-way groups: Damon and Wahlberg lead; Baldwin and DiCaprio are debated; Sheen, Farmiga, and Nicholson are criticized. This is a structured discussion, but no formal category or flex cue is spoken.
Approx. transcript time · 00:29:46Read transcript
After the winner, the panel argues that Nicholson loses the movie through a loose, inconsistent performance and accent, while acknowledging that his entertaining excess may help rewatchability.
Approx. transcript time · 00:48:19Read transcript
DiCaprio and Damon swapping roles is tested; the panel thinks Damon could play Costigan but DiCaprio could not play Sullivan as effectively.
Approx. transcript time · 00:53:08Read transcript
Dignam killing Sullivan is praised for the outfit and catharsis; reported Departed 2 pitches involving Wahlberg are discussed.
Approx. transcript time · 00:54:19Read transcript
The panel argues that The Departed’s flaws and loose ends help make it rewatchable, contrasting its roller-coaster quality with the tighter No Country for Old Men and the deliberateness of Heat.
Approx. transcript time · 00:55:51Read transcript
Infernal Affairs is recommended as entertaining and tighter than the remake.
Approx. transcript time · 00:59:06Read transcript