The casting what-ifs are called probably the best for any movie they have done, a whole alternate Departed. — Bill Simmons
Pitt bought the producing rights, planned to play the Damon part, then decided he might be too old and went to do Babel. — Bill Simmons
Debate over Pitt: good instincts about roles and a great producer, but miscast himself in Meet Joe Black and The Devil's Own; Damon was the better choice.
Ray Leota was the original choice for Dignam but declined over other commitments, his 2006 films including Comeback Season, Local Color and Even Money. — Bill Simmons
Dennis Leary was the second choice for Dignam but had to make season three of "rest of me" (as transcribed); he would have been great, though Walberg is perfect. — Bill Simmons
Ellerby was offered to Mel Gibson, who was starting Apocalypto; Queenan was supposed to be De Niro, who made The Good Shepherd; the Anthony Anderson role was meant for "the Rizza" (transcript form, unresolved), who was too old or had conflicts. — Bill Simmons
Leo was in The Good Shepherd but dropped out to play Billy Costigan, and Damon then took The Good Shepherd role; The Good Shepherd is called an unexamined movie with a dynamite cast.
The alternate cast (Leo, Pitt, Pacino, Leota, De Niro, Mel Gibson and the Riza) is called pretty loaded and preferred by one participant; Pacino would lose Costello's lumbering physicality but gain CR doing Pacino.
Would-you-rathers: Walberg over Ray Leota, Baldwin over Mel Gibson 100 out of 100 times, and De Niro over Sheen since he can underplay.
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
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. — Bill Simmons
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. — Sean Fennessey
Flip phones as a central character are listed, but also called a nice time capsule. — Bill Simmons
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. — Bill Simmons
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. — Bill Simmons
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. — Bill Simmons
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. — Chris Ryan
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. — Sean Fennessey
John Lennon's "Well Well Well" plays and then Nicholson opens a John Lennon speech, called ridiculous though entertaining. — Sean Fennessey
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. — Bill Simmons
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
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. — Bill Simmons
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. — Bill Simmons
Damon's real contempt for firemen, and the credits arriving 18 minutes in. — Bill Simmons
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. — Bill Simmons
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. — Bill Simmons
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. — Bill Simmons
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
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. — Bill Simmons
Borderline pick: Damon's first date with Vera, well written and acted. — Bill Simmons
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. — Bill Simmons
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. — Bill Simmons
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. — Sean Fennessey
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. — Bill Simmons
Lin Shaye describing what is happening and using the word insidious is the Leo from Once Upon a Time pointing-at-the-screen moment. — Bill Simmons
A participant proposes the Leonardo DiCaprio pointing-at-the-screen moment as a Rewatchables category, loving when the title is used organically in dialogue. — Chris Ryan
A reply says the best one ever is Face Off ("take his face off"). — Chris Ryan
DiCaprio as John would work by making him 13 and nudging the war to 2000, countered that the first film fixed the date.
Michael Biehn as the T-1000, out of respect for an under-appreciated glue-guy actor who was the hero of the first film and was off shooting Tombstone while everyone returned.
The pick is called porn for Chris, president of the Biehn fan club, and Biehn's appearance in The Mandalorian is celebrated.
DiCaprio won the movie: he plays about six versions of Rick, plus roles within roles, a mind-blowing piece of acting. — Chris Ryan
He or Driver is the best actor of 2019. — Chris Ryan
Tarantino wins all of his movies; no one else could have made it. — Chris Ryan
Pitt won the movie: the host had given up on him after a public breakup, and he came roaring back. The hosts rarely split like this. — Bill Simmons
The audience is polled by voice on DiCaprio, Tarantino and Pitt; the Pitt cheer is taken as agreement. Audience cheers are not counted as ballots. — Bill Simmons
It easily could have been a 10-episode series, and many directors would have taken the streaming money; Tarantino has experimented with extended cuts on Netflix.
Tarantino has talked about making Bounty Law episodes, possibly for Netflix; DiCaprio is guessed not to do it.
Pitt ad-libbed "You're Rick fucking Dalton. Don't you forget it," based on an unnamed actor who told him the same in the early '90s; the hosts guess jokingly at who it was. — Bill Simmons
Rick recoiling from the flamethrower's heat was DiCaprio's genuine reaction, which Tarantino kept.
The Cadillac belonged to Michael Madsen, the same car from Reservoir Dogs.
The theater Sharon Tate and J.C. Bring discuss at El Coyote is now the New Beverly, owned by Tarantino. — Bill Simmons
A framed Mad Magazine in Rick's apartment was made as a full magazine with jokes, as Tarantino told the hosts. — Bill Simmons
Tarantino wrote a novel-like backstory of Cliff and Rick before the screenplay. — Chris Ryan
The Maltese Falcon Sharon holds in the bookstore is owned by DiCaprio. — Bill Simmons
Trudi was inspired by a character from Lancer; some think she draws on Jody Foster. — Bill Simmons
