Wolf’s screenplay is said to draw on personal experiences; a 2017 Entertainment Weekly oral history describes the filmmakers’ sense of responsibility toward the antisemitism theme. — Bill Simmons
A replayed 2018 Damon interview describes being cast by Jaffe and Lansing as a major credibility boost, followed by returning to college without work; publicity emphasized Fraser and O’Donnell because they had follow-up films.
In the interview, Damon rejects the suggestion that playing the villain itself was held against him; his hurt concerned the publicity focus on the other actors.
Fraser reportedly stayed in a separate hotel and socialized apart from the others, paralleling David’s outsider role. — Juliet Litman
The stated budget is$18 million and gross$14.7 million, with long-term cable and home-video income speculated to have made up the difference. — Bill Simmons
Rapp reportedly could not see through the glasses he wore as Magoo and acted without clearly locating the others. — Bill Simmons
Filming took place at Middlesex School in Concord and other prep schools. — Bill Simmons
The shower fight reportedly ran out of hot water, with artificial steam used around cold water. — Bill Simmons
Mandel reportedly encouraged the actors by predicting they would be the next Brat Pack. — Bill Simmons
McGivern’s French assignment is identified as Keats’s On Seeing the Elgin Marbles for the First Time. — Bill Simmons
The young cast are said to have all auditioned for Scent of a Woman, which O’Donnell won. — Bill Simmons
David’s 42 is interpreted as a Jackie Robinson reference, while Dillon’s 21 is proposed as half-the-man symbolism; the symbolic interpretation is not independently confirmed. — Bill Simmons
O’Donnell recalls the group lifting weights with the UMass Lowell football team and Damon as the strong one. — Bill Simmons
Fraser says he faked much of the football and disliked getting hit despite later making a career of physical roles. — Bill Simmons
Locane recalls Fraser remaining apart from the others’ fraternity-like social group, perhaps for the role. — Bill Simmons
The football uniforms’ colors, stripes, and helmets are admired, with a reservation about the body of the uniform. — Bill Simmons
The ancient graduate from the class of 1875 is enjoyed as a link to the Civil War era, while his apparent 98-year-old vigor is questioned. — Bill Simmons
Ed Lauter as David’s father is appreciated as a sports-film presence, with a wish that he attended the major game despite the travel distance. — Bill Simmons
The honor code is praised as an effective dramatic device precisely because it fails under pressure. — Bill Simmons
Scranton remains a legible hometown reference, partly because of The Office. — Juliet Litman
Cheating is praised as a reliable source of conflict and debate. — Juliet Litman
The tweed coats and blazers are admired. — Juliet Litman
The Scranton youths’ James Dean styling and the Rebel Without a Cause marquee are enjoyed. — Mallory Rubin
The luncheonette and Skip’s Diner are admired as neighborhood gathering places. — Mallory Rubin
Youth dances and the meeting of boys’ and girls’ schools evoke record hops, enforced distance between dancers, and camp memories. — Mallory Rubin
Dillon’s fumble, missed tackle, forced block, and despondent expression are considered ideal material for a modern meme. — Mallory Rubin
High-school football boosterism and recruiting the player needed to defeat a rival are praised as enduring traditions; David having to work a real job is contrasted with Friday Night Lights. — Mallory Rubin
Damon’s villainous performance is praised as an underused side of his screen persona. — Mallory Rubin
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. — Bill Simmons
Colin's impotence ties to his whole life being a lie and a performance.
His "I'm fucking Irish" speech to Madeline is judged sincere, his most Billy moment, with a Jets joke.
Whose baby is Madeline carrying: one thinks Colin's, others argue Leo's since only Billy is shown having sex with her. — Bill Simmons
Why Madeline does not turn Colin in despite the evidence; her exit is abrupt. — Bill Simmons
If Damon and Leo switched parts: worse, since nobody could do Costigan better than DeCaprio, versus Damon could have done it (Courage Under Fire, The Last Duel).
Why the name Dignam: one of Monaghan's naming flourishes.
Costigan's bad deal and psychology; death-wish motivation; Queenan and Costello missing the rats; Colin's interrogation interference; the left envelope; the lawyer's tapes; Combat Zone anachronism; two dates of birth; nonexistent apartment
Why Costigan agreed to such a terrible deal; his split-family psychology and being challenged as a rich boy do not explain it, and his violent history should have kept him out of the academy.
The tax-free pay written on paper and whether he is a thrill-seeker; one view is a death wish the movie did not sell correctly.
Which is more unrealistic: Sheen not realizing Damon was the rat despite his calls, or Costello not realizing Leo was. — Bill Simmons
Damon turning off the interrogation camera and later losing the tail stretches disbelief, partly explained by Badge Dale also working for Costello.
Costigan sees the Citizens Bank envelope, leaves it displayed and runs, botching the moment despite supposedly high SITs (as transcribed). — Bill Simmons
What if Costigan never saw the envelope: the movie just ends with more impotent sex. — Sean Fennessey
Costello's lawyer giving Costigan the tapes is a stretch. — Bill Simmons
The Patriot Act dates the film to at least 2002, when the porn theaters were gone; Costigan's record shows two dates of birth; the apartment does not exist. — Bill Simmons
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". — Bill Simmons
"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. — Bill Simmons
Alec Baldwin, no (30 Rock); Southie and extended Boston, no, done better; Vera, no (Conjuring, Up in the Air). — Bill Simmons
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.
On-set friction; Whitey Bulger basis; The Wire offer to Ray Winstone; Scorsese's surprise at winning; Wolf of Wall Street yacht; X motif; Ballhaus's last collaboration; tax credits; Monahan sequel idea; F-word count; VHS; Psycho shower homage
"Him and Nicholson" reportedly did not get along on set (the referent is unclear in the transcript). — Bill Simmons
Nicholson wanted it to be more than a gangster film, so Monaghan based Costello on Whitey Bulger; the window view behind the rat nods to Little Caesar, Scarface and White Heat. — Bill Simmons
Ray Winstone was supposed to play Jimmy McNulty but turned it down because he did not want to move to Baltimore. — Bill Simmons
Reportedly the director was surprised the film won and never thought about awards, finding it too nasty and violent and a remake; the yacht behind Frank is the same yacht as in Wolf of Wall Street. — Bill Simmons
X motif sightings: airport walkway crossbeams, taped windows where Queenan is thrown, behind Costigan in the elevator, and the carpet when Damon returns. — Bill Simmons
This was the last Scorsese-Ballhaus collaboration; an early attempt to shoot with more Infernal Affairs-style whip pans was dropped; later films with Robert Richardson and Rodrigo Prieto look totally different.
Shot mostly in New York for its 15% tax credit, the film prompted Massachusetts to adopt a 25% credit and 15 years of movies filmed there. — Bill Simmons
Monahan described a sequel set before, during and after the first film, showing off-screen actions; the reply from Scorsese was no thanks; Walberg talked about a Dignam sequel, and Ted Sarandos is urged to make one.
The count of the F word is given as 112 and 238 (unclear which is the answer) with a sense it is undercounted; it was the first Best Picture winner not released on VHS.
The shower shots before Madeline listens to the Costigan tape repeat the three shots of Psycho's shower scene. — Bill Simmons
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.
