Jail pickup coffee, Will explaining jokes, sharp art criticism and the four friends’ complementary personalities are praised. — Bill Simmons
The lasting Damon/Affleck partnership and Williams’s dramatic legacy are strengthened by the film; Coppola’s connection reportedly helped secure him. — Bill Simmons
The exuberant Oscar speech and the film’s impact on Boston-accent popularity are recalled. — Bill Simmons
Friendship, cardigans and Chucky’s tracksuits are favorites; a reported costume disagreement led to rushed Reebok replacements.
All four friends’ later success and Affleck’s uninhibited DVD commentary are celebrated. — Bill Simmons
Plimpton’s therapy scene, the opening bar insult and Lambeau’s inappropriate flirtation/math-is-erotic moments are memorable comic details. — Ryen Russillo
Nominees are Casey Affleck, Minnie Driver, Cole Hauser, Professor Lambeau and Lambeau's TA, who seemed in love with Lambeau and became immediately threatened by Will Hunting; Robin Williams is not made eligible; honorable mention to George Plimpton as the psychiatrist Will psychs out by calling him gay.
Casey Affleck is proposed as a great heat check performance, and later a host says they have Casey for this: a nothing part he made fun and really interesting, impossible to describe, with the joke that Affleck is the Dion Waiters whose brother Rion gets enough field goal attempts.
Stellan Skarsgård is called high level: doing a lot of crazy stuff, and on rewatch a huge creep, the classic professor hitting on students, asking for a drink and calling Skylar too; he sells the tortured genius who realizes there is someone more genius than he is; no casting what-if was found for his role; Casey has nine of the movie's 20 best lines.
It is between Casey and Skarsgård, but the pick is Cole Hauser, because there was not enough of him; the best Cole Hauser part is the back of the car, when Cole is messing with Casey, Casey says he is going to fight him now, and the smile drops off Cole's face as he is ready to go. — Shea Serrano
Hauser should have only ever played that character and been an action guy, in some movie where somebody kidnapped his daughter, or Paparazzi; he is good whenever unhinged, including as the bad guy in Too Fast, Too Furious despite the dyed hair; he is the darkest, scariest guy in the crew, who has absolutely killed somebody: even Matt Damon warns Clark and Ben Affleck tells Casey to get out of the car, but Cole never says anything and is just in the action.
A tangent on dangerous but fun bars in Philly and Boston, where neighborhood drifting has faded with gentrification; one host lived in Charlestown two minutes from the original Sully's, townies only, where he would have gotten the shit kicked out of him, and Cole's stare at the table when Casey Affleck pisses him off is deep Boston.
Honorable mention heat check to the screenwriters for naming a guy Carmine Scarpaglia, a heat-check move to show there are Irish guys and Italian guys, like Italian movie name bingo.
