The Nicholson–DiCaprio confrontation repeatedly asking whether he is still a cop is nominated. — Bill Simmons
Queenan’s rooftop death and body fall are nominated. — Bill Simmons
Wahlberg killing Matt Damon at the end is nominated. — Bill Simmons
Sullivan calling Costigan on Queenan’s dead phone is nominated. — Chris Ryan
Costigan’s sudden elevator death is nominated and remembered for making the theater gasp. — Chris Ryan
The opening briefing with DiCaprio, Baldwin and Wahlberg is explicitly selected as most rewatchable. — Chris Ryan
The rooftop meeting with Queenan is described as the part one host always watches, including Queenan’s fall and the reaction afterward. — Bill Simmons

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14:38

Casting What-Ifs

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

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. — Bill Simmons
Ray Leota was reportedly set for Dignam but could not do it. — Bill Simmons
Denis Leary was the next reported Dignam possibility and also could not do it. — Bill Simmons
Al Pacino was the first reported Costello choice and is debated as an alternate. — Bill Simmons
Robert De Niro reportedly declined Queenan to make The Good Shepherd. — Bill Simmons
Mel Gibson reportedly could not play the Alec Baldwin part because he was filming Apocalypto. — Bill Simmons
RZA was reportedly offered the Anthony Anderson role. — Bill Simmons
Nicholson’s proposed prostitute scene and retained dildo improvisation are presented with explicit uncertainty. — Bill Simmons

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17:36

What’s Aged the Best?

DiCaprio versus Damon, the delayed title, Baldwin and Wahlberg’s department, the cranberry-juice scene, Costello’s de...

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. — Bill Simmons
The title arriving about eighteen minutes into the movie is praised. — Bill Simmons
Costigan’s jail workout is part of the delayed-title sequence. — Bill Simmons
Alec Baldwin and Mark Wahlberg running an internal-affairs-on-internal-affairs department is praised. — Bill Simmons
The cranberry-juice confrontation is praised as a perfect scene. — Bill Simmons
Costello’s death is nominated. — Bill Simmons
Dropkick Murphys entering with the title is praised. — Bill Simmons
The Dropkick Murphys cue is linked to the closer transcribed Papoban and the Red Sox era. — Bill Simmons

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21:24

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. — Bill Simmons
Mark Wahlberg’s hair is criticized. — Bill Simmons
Costigan’s panic and handling of the Citizens Bank envelope are questioned against his established intelligence. — Bill Simmons
Costigan’s plan to trap Matt Damon’s character on the same roof where Queenan died is questioned. — Bill Simmons
Damon sending a complicated T9 text in his pocket is the explicit winner, with agreement, and is considered implausible and dated. — Bill Simmons
The Chinese-microchip subplot is dismissed as confusing. — Chris Ryan
Scorsese’s third use of “Gimme Shelter” is criticized as overuse despite other strong Stones choices. — Bill Simmons

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25:32

The Joey Pants “That Guy” Award

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

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. — Bill Simmons
James Badge Dale is nominated as Trooper Barrigan. — Chris Ryan
Anthony Anderson is nominated as a 2006 That Guy who later became a name. — Bill Simmons
David O'Hara is nominated as Fitsy. — Bill Simmons
Mark Rostin is one host’s winner because of his Shawshank identity as Boggs. — Bill Simmons
Kevin Corrigan is the other host’s winner as the perfect Costigan cousin. — Bill Simmons
The hosts end by agreeing to disagree rather than naming co-winners. — Bill Simmons

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28:40

Half-Assed Internet Research

Winstone and Nicholson’s friction, Nicholson’s Red Sox/Celtics refusal, DiCaprio’s project choice, accent coach Jay G...

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. — Bill Simmons
Nicholson reportedly refused a Red Sox hat and banned Celtics hats on set. — Bill Simmons
DiCaprio left The Good Shepherd to make The Departed. — Bill Simmons
DiCaprio’s Boston accent coach is named as Jay Giannone. — Bill Simmons
The film is reported to use “fuck” or derivatives 238 times. — Bill Simmons
Wahlberg reportedly based Dignam on a compilation of people who arrested him as a youth. — Bill Simmons

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35:46

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. — Chris Ryan
Costello’s dildo is nominated. — Bill Simmons
The flip phones are nominated as funny in retrospect. — Bill Simmons
Sullivan’s impotence material and Baldwin’s “mine’s working overtime” line are nominated. — Bill Simmons
Nicholson’s three-second run is selected as the funniest moment. — Bill Simmons

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38:32

Picking Nits

Costigan accepting undercover erasure, the impossible statehouse view, the central romance, Madolyn’s inaction, an in...

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. — Bill Simmons
Damon’s character’s impossible statehouse apartment view is questioned. — Bill Simmons
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. — Chris Ryan
the doctor not turning Damon’s character in after Costigan’s death is questioned. — Bill Simmons
Casting a forgettable actor as Costigan’s killer is debated against using a more famous face that would telegraph his purpose. — Bill Simmons
Queenan’s failure to suspect Damon’s character despite obvious suspicious behavior is questioned. — Bill Simmons
The literal rat at the end is criticized as an overly explicit symbol, then partly defended as a closing bow. — Chris Ryan

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45:23

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 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. — Bill Simmons
The guy who does his job / the other guy exchange is nominated without adding a character attribution absent from the cited segment. — Bill Simmons
Dignam’s “maybe, maybe not, maybe fuck yourself” and dead-phone lines are nominated. — Bill Simmons
Costello’s environment line and other aphorisms are nominated. — Bill Simmons
The world needs plenty of bartenders is nominated; the immediately following Two weeks with pay receives the explicit favorite status. — Bill Simmons
Costigan’s request for two pills and joke about scotch and a handgun is another favorite. — Chris Ryan

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47:14

Who Won the Movie?

Leonardo DiCaprio

In the discussion (4)

Approx. transcript time · 00:47:14Read transcript

The choice is Leo, followed by agreement on Leo winning the movie. — Chris Ryan
Mark Wahlberg is described as overwhelming on early viewings before the preference shifts to DiCaprio. — Chris Ryan
Matt Damon is praised for his creep performance and as the structural counterpart. — Chris Ryan
Nicholson is said to lose the movie because of excess. — Bill Simmons

Podcast choices

Speaker not identified: Leonardo DiCaprio
Speaker not identified: Leonardo DiCaprio

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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