The host could not narrow the categories to five or six because this is not just a great movie but the quintessential cable movie, on some channel for 20 years and constantly tested by people coming in partway; the nominees are the slow-motion playground fight, the battle with Ponytail Guy, the I Will End You scene, the park bench monologue, Pudge Fisk, the twelve-minute stretch from Will laying into Lambo through the baseball glove and the shepherd scene, the Chucky construction best-part-of-my-day scene, It's Not Your Fault, and Chucky realizing Will left.
The Red Sox story, the Pudge Fisk story, is the scene you stay for when you come in with five minutes: funny coming from a Philly fan, relatable, with a twist you know is coming; Damon cracking up and getting genuinely locked in shows the connection being made without talking about therapy, the physical acting Robin Williams does is great, and the filmmaking cuts in the game footage and the overhead shot of him reenacting the scene. — Chris Ryan
In the overhead shot the furniture is set up like the bases; the filmmakers were not sure they would get the baseball footage, having licensed nothing at that point, and Harvey Weinstein had to make it happen, because the scene would not work as well without the baseball.
The issue with the scene is that nobody who loves the Red Sox gives up a Game Six ticket at Fenway after only two World Series in 28 years, in 67 and 46, however much he likes the girl; it is the same problem as Fever Pitch, where Jimmy Fallon gives up fourth-row tickets for Drew Barrymore; this host would have been the friend saying there is no way you skip this game, and concludes Sean was an artsy-fartsy smart guy whose friends were like Jerry Lambeau and not real Red Sox fans, which the others call a take and a half and compare to a limousine liberal quoting Leo from The Departed.
The ponytail scene with Clark sets the movie in motion and is the only nominee that gives a bit of what makes every character great: Ben Affleck charming and funny without being threatening, Minnie Driver making her little comment to Clark that makes Matt Damon smile, Damon flexing for the first real time how much smarter he is, not wanting to do it and being forced into it to save his friend, and the quick Casey Affleck shot, boy, he's wicked smart; there is no way to skip past that scene. — Shea Serrano
The nitpick with the Clark scene is that Affleck and Cole Hauser would throw down with Ponytail Guy immediately, before it ever gets to the Will Hunting part, since these are guys who randomly drive by a playground and fight five guys; the hosts also ask why it matters that Casey is bouncing at a bar in Cambridge, concluding the Southie guys wanted to try a new bar, mix it up and make fun of people, and that it is a totally realistic Boston scene of people drifting from neighborhood to neighborhood.
Why a local group from Southie would want a Harvard bar: a different type of girl than they are used to, and they cut the line because the bouncer lets them in; yet inside it is not populated and is basically a sports bar with Papa Shot (as transcribed) and Bud Light, though Harvard Square had popular holes in the wall like Charlie's; one host recalls the townies-versus-college-kids separation in Huntsville, Texas, and those guys looking for conflict is the point, with Cole Hauser punching that guy in the face immediately.
An honorable mention is the Retainer scene, Ben Affleck flexing in front of the three guys; this was way more Ben Affleck's movie than remembered, so funny, charming and weird that it is a shame he is not this actor all the time; the scene responded to most is the fight, though it is so short it may not draw you in on cable, and it is the weirdest thing ever, since why are they fighting these guys. — Sean Fennessey
Will fights the guy because he got picked on in kindergarten; Will Hunting should be in prison for life, and when the judge, who is not Vonnegut but an actor who was a member of Whitey Bulger's Winter Hill gang, reads the rap sheet of assault, grand theft auto, larceny and mayhem, this guy clearly cannot be let out to clean hallways; a Gus Van Sant fight scene is not something that crosses your mind, and Casey Affleck's face as he falls to the punch is phenomenal.
One host's single favorite is the Chucky construction scene, when Chucky gets mad at Will for still being there and says before he knows it he will be 50 and still doing this: a Massachusetts thing of living and dying in your parents' house, with Chucky the perfect character whose friends are the most important thing to him, down to the casual mention of still watching Patriots games, nuances William Goldman never could have written; Affleck had been ready to do that scene for years and nailed it in the first take, doing two more takes but the first was used.
The construction speech is mostly shot over Affleck's shoulder going in on Damon across the hood of the car, not the usual framing for a memorable scene, so you expect Damon to have a big rebuttal and he does not; the clip is played, from 'it'd be an insult to us if you're still here in 20 years' through the best part of my day being the ten seconds hoping Will will not be there.
Part of the rewatch pleasure is the 20 years of history with Damon and Affleck, who are both obviously stars in this movie, like an NBA team with two future superstars; the script started with Damon at Harvard, based on his relationship with a woman named Skyler, before he brought it to Ben, and the movie forecasts the tension of what happens when one of them makes it and the other does not.
The last eight or nine minutes are as rewatchable as any movie's ending: Will saying goodbye to Sean, Sean and Lambeau getting a beer, Chucky going to pick him up and finding him gone, and the credits rolling over the car with Elliot Smith; the hosts cannot place the highway, which feels like the Mass Pike but was probably outside Toronto.
Casting what-ifs are knocked out fast because the movie cannot be imagined with anyone else; Harvey Dent is called secretly very good casting because the part needed someone who thought he was a big deal but actually was not, which is perfect for Aaron Eckhart, a shot another host, who loves Eckhart, pushes back on with a joke about a Gulf Coast condo built on Eckhart stock.
Actors who expressed interest or auditioned for Harvey Dent: Josh Lucas, not heard from much since Glory Road; Liev Schreiber, judged a little too dark and stormy for a Dent who has to start as a golden boy, though he could have been a good Two Face; Mark Ruffalo, rejected as way too cerebral and neurotic; and Matt Damon, which prompts the question of why Damon just wants to be in a Christopher Nolan movie.
Young, Courage Under Fire-era Matt Damon would have made a great Robin.
Christopher Nolan is quoted as never really having considered anyone but Heath Ledger for the Joker, which is dismissed as what they say after the fact; actors rumored for the role were Paul Bettany (fine), Steve Carell (no), Robin Williams (maybe in a Tim Burton movie, a little too ghoulish), Adrian Brody (as transcribed; 'I can see it') and Ryan Phillippe, who is said to turn up more than anyone in lists of roles he did not get and to have been in the final three for Captain America with Krasinski and Chris Evans, which usually means great publicist, bad agent.
Ledger's performance is so legendary, arguably the most iconic movie performance of the 21st century, that nobody can be put in the role; an actor rumored for it would be wise to scrub that from the internet.
William Fichtner's bank manager is said to have been offered to Dwight Yoakam, who was busy recording Dwight Meets Buck, prompting the question whether that is a Buck Owens cover record; the hosts love Yoakam as a movie actor, a legend in Panic Room and Wedding Crashers with a quiet malevolence on screen, though he would not have been right for this particular role.
Kate Winslet had to do a screen test, watchable online, opposite Jeremy Sisto, Elton from Clueless, who auditioned but probably was not in contention; the major name in contention for Jack Dawson was Matthew McConaughey.
Stephen Dorff is the verified one: a New York Daily News piece headlined 'actor is thankful he didn't get Titanic role' has the Blade co-star saying he wanted a career like Johnny Depp, Sean Penn and Jack Nicholson and an Oscar, which Titanic would have made impossible, and that Leo will always be the guy on the boat.
One host disagrees that Leo is the guy on the boat, since he has been in so many hits and everyone has a favorite Leo, whereas Matt Damon and Ben Affleck are more locked into their 90s work; Sofia Coppola is said to have made Somewhere with Dorff because he never blew up, and Titanic will be in the first line of DiCaprio's obituary, and of Billy Zane's.
Billy Zane has not done much anyone has heard of since, though he has been in three times as many films as Kate Winslet.
Chris O'Donnell, named on Wikipedia for Jack, would have been a great and adorable Jack given his Batman movies and a season-two television arc, but could not have taken the film past a billion dollars; Leo is singular and the chemistry is enduring, though he seems strikingly innocent and little in it.
Rob Lowe was in the mix for Cal and is a great asshole, as in St. Elmo's Fire; pre-West Wing he might not have pulled viewers out of the film, though one host says he would have a little, and the leads mostly had blank or clean reputations at the time, which the hosts think mattered.
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
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
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
JT Walsh gets an 'Apex for me for sure' and a second yes calling it his most infamous role, prompting a joke about how seriously the question was taken.
Aaron Sorkin is close but not the apex, a nice view but not the top; the first season of The West Wing and The Social Network are his apex, this film is likened to his 63-point Michael Jordan game with not a bad scene in it, and Moneyball is set aside because he rewrote somebody else's script.
Kevin Pollack is a no because of The Usual Suspects, which another agrees with.
Kevin Bacon is a no from one panelist, who calls him great and underrated here but notes how many films he has made, with The River Wild mentioned; another says no too, theorizing his bad haircut was deliberate so he would not distract from Cruise, like Kiefer's haircut, and puts his apex at Footloose, also liking him in Mystic River.
A third panelist disagrees with both and says this is Bacon's apex: not a meaty part but memorable, likable, with a dash of unintentional comedy, and hard to imagine anyone from that era, such as Matt Dillon, playing it without competing with Cruise.
Bacon was taking smaller parts in bigger movies then, as in JFK; though he is on the prosecuting side backing Jessup, he has some morality, saying he does not think the guys deserve jail but does not make that call; after an aside that his leaving the pickup game is unforgivable, a 'yes' for him is restated, possibly by the same panelist.
Wolfgang Bodesen (as transcribed) is a yes: 'that's the Apex for Wolfgang. I wish him well.'
Jack Nicholson's career overall draws four 'No' answers; then 'Late Jack Nicholson. Yes.' is offered, with one voice naming As Good as It Gets, and challenged over The Departed the late-career yes holds, because the Departed performance with its accent as a Whitey Bulger figure is called out of control and the weak link of that film.
Tom Cruise gets two yeses, with this chosen over Cocktail and a 'this or The Firm' aside; no one else in 30 years could bring this mix of unintentional comedy, good acting, sarcasm and bravado, Leo DiCaprio could not, though Matt Damon ten years later might have.
A TV version is planned for next year with Alec Baldwin, who is called amazing, but Caffey has not been cast; James Franco was rumored, a terrible idea, since the part needs an airhead who is really smart, a lawyer who plays softball, attractive but not a romantic lead; Demi Moore is left off the list as the nadir of her career.
