Three candidates, Damon, Affleck and Robin Williams; the first vote goes Robin Williams because it is his best performance and he is not alive, so a posthumous Oscar montage will center on It's Not Your Fault, which the hosts reenact.
The case for Robin: there was no point where he got beat in any scene, always the best guy in a movie full of great actors and actresses.
The dissent goes Damon: the Williams performance is irreplaceable, but Damon has to do dumb, smart, physical, romantic lead, tough guy and genius, convincing in the memorized history lesson in the bar and the Bobby Chucky Tommy Ricky bit, crying and being a boyfriend, and other people could have played the Williams part well while nobody else in 30 years of actors makes the Damon part work.
If Leo were in it, as in the Departed scene-swap debate, it would be missing five percent of the authenticity and Boston DNA, more like Catch Me If You Can; Damon seems tough, like he could kick the shit out of you; Brad Pitt is good at playing dumber than he is, in True Romance and Seven, but not smarter, so he could not do the revolutionary America economic speech, though he could have done Chucky, except he is too short.
The argument for Williams over Damon comes down to the it's not your fault scene, where Williams overpowered him a little, but Damon holds his own in their first big scene with the painting; a Robin Williams and Minnie Driver scene is wished for and is probably deleted somewhere.
What actress plays Sean's wife in a flashback? How long did Will stay with Skylar, and what became of Will, Chucky, Casey Affleck's and Cole Hauser's characters? Why have Damon and Affleck not made another movie together, and why was Affleck not in Ocean's Eleven? Is this the best Boston movie of all time?
The block opens with the remake-as-series question, recorded separately.
If there were a flashback with Robin Williams and his wife, what actress plays her: Deborah Winger (as transcribed) is offered; she has to look like a lifelong Boston lady; Amy Ryan from The Wire, Bonnie Bedelia, not Boston-y enough, and jokes of Conan O'Brien and Mark Wahlberg.
How long did Will stay with Skylar, presuming he makes it to Stanford and finds her, which as a genius on early internet message boards he would: a semester, or three or four good weeks before it falls apart when they get drunk and she says you told me you didn't love me; Lambeau would have to be Will's reference since nobody else knows about him.
What happens to these people: Will becomes an asshole hedge fund manager and Chucky becomes Matt Patricia, Sharpie in his hat, crunching tape for Belichick; or Will shows up, she is happy, they go to a Stanford party where a kid makes fun of his accent, Will beats the shit out of him and goes to jail, she bails him out and within three weeks they have broken up; twisted further, it becomes a prison movie, a shot caller situation where he joins a gang and, being a genius, figures out how to break out, Good Will Hunting 2 in jail in Palo Alto.
Or he obviously becomes a tech billionaire, a Steve Jobs-ian figure in late-90s Northern California with a doctor wife-to-be and a difficult childhood; or he becomes Sean, a therapist, which one host refuses; or they realize it will not last, he goes back to Boston, Sean has died of a heart attack and he works construction, that friend; or 15 years later stories of his crimes and anger come out; or Chucky fulfills his promise to kill him and it becomes Face Off across Boston, Good Will Hunting 2: Hunting Will.
What if Good Will Hunting 2 had been The Town, with Damon's life having failed; whether Affleck tried to convince Damon to take the Renner part is debated, and whether Damon can play that kind of crazy at all, since Talented Mr. Ripley was reactionary crazy, with the hosts directly challenging his acting.
Why have these two not made another movie together: they went separate ways professionally, have a Showtime show coming that is basically a Wire for Boston, and the Fritz Peterson Yankees wife-swap movie fell through; Affleck has proven a great director and there is a great writer in Damon who should try again instead of The Great Wall; a theory that Affleck does not want to because Damon does not look cool anymore, or is mad he was cut out of Ocean's Eleven; whether Ben would have improved those movies in Casey's place or as the Andy Garcia role, though he needed to be older.
Zach Mack (as transcribed) is asked which of the five sequels he liked most, picking Chris's; the prison pitch and Hunting Will are recalled, plus Will Hunting with a shotgun and a beard in 2018; if Skyler tells him to get lost in Palo Alto, does he spin out, become a custodian at Stanford waiting for her, which is creepy, or go Zuckerberg and create Facebook, you'll see, Erica Albright.
The biggest criticism of the movie has been that it's not your fault is treated like a cure for abuse the film takes pains to establish, a guy putting cigarettes out on him, so that he hops in a car knowing how to love; if he is cured he is wealthy and with Skylar, if it moved too fast they break up after three weeks and he becomes a shot caller, still damaged and violent.
Chucky now is 42 and leading or assistant foreman of his uncle's construction crew; Southie is much nicer and his crap house is worth five times as much, so he stayed or sold; maybe he took over the bar with Cole; Cole Hauser owns an auto shop and got murdered by an IRA customer, or was the muscle in a different Boston crew; Casey Affleck moved to LA to see Will, stayed, became a comedian and lives in the pool house; Will's friends came out within a year and it went badly.
Asked how badly the visit went: Cole killed the guy, and they buried the body. — Shea Serrano
The alternative is that the guys get arrested by TSA getting off the plane at LAX, too tanked, and are put on a jail plane back to Boston without seeing Will.
Last question, probably answerable: is this the best Boston movie of all time; The Friends of Eddie Coyle is one host's favorite; another does not really care about Boston, having been three times without knowing Cambridge from Boston, and would rather watch The Departed; the qualifications for a city's signature movie are that it is awesome, uses the city, is authentic and could only have taken place there, like Rocky and Creed for Philly; the final three are The Departed, Good Will Hunting and The Verdict, with The Town fourth.
Friends of Eddie Coyle is liked here too, with a sense one is being forgotten; the first hour of Social Network is a really good Boston movie. — Chris Ryan
The Departed did not shoot much in Boston and Good Will Hunting shot a lot in Toronto, like Den of Thieves, set across LA but shot in Atlanta; the answer given is The Verdict, which uses the city best and has the authenticity, with Good Will Hunting very close, a 1A and 1B.
Earlier, the film is called possibly the best Boston movie ever, on the short list, a discussion saved for later.
A new category suggested by a reader, whose name the host cannot remember: the Mark Ruffalo They Knew overacting moment of the movie; watching for the first recipient, there is no overacting in this movie, and the only case, which the host does not agree with, is Chucky going in to do the job interview for Will, a comic relief scene everyone likes.
Devil's advocate: does Damon broadcast the cracking in it's not your fault, or is it just familiarity after 25 years; it is one of the only times Robin Williams blows Damon off the screen, and if you look closely the crinkled-up face when he starts to cry is kind of bad until the hug hides him, which is why people have picked on the scene over the years; the rebuttal asks how else he should play a man melting down and trying not to.
Given the final say, the answer is that Damon does a good job in that scene; also, Mark Ruffalo's they knew line is the best part of Spotlight. — Shea Serrano
The others love the Spotlight moment too, having waited Ruffalo's whole career for him to raise his voice in a movie of people reading phone books for two hours; the category is tweaked to the overacting scene they also love to death, achievement in overacting, and given to Clark with the ponytail, exactly over the top perfect, even his ponytail a little frazzled.
Agreement that Clark is the pick, given his look. — Chris Ryan
Shout-out: the Clark actor became more famous in Oz as Ryan O'Reilly's brain-damaged brother, and is Dean Winters's real-life brother; Ryan O'Reilly is a forgotten all-time great TV character, and Winters is now the beeper guy from 30 Rock and the insurance ads.
The Public Garden bench is now a Robin Williams memorial; a gay sex scene was written into the script to test whether anyone read it; Williams insisted on the L Street bar and ad-libbed the wife story and 'Son of a bitch, he stole my line'; Sean was based on Damon's mother and Affleck's father; Gus Van Sant painted the painting in Sean's office; Skylar was based on Damon's Harvard ex; Damon and Minnie Driver dated through the shoot and the Oscars; Terrence Malick suggested the ending
The Boston Public Garden park bench where 3,000 people watched the scene is now a memorial to Robin Williams, after people put flowers there when he died; one host lived for ten years a six-minute walk from Bunker Hill Community College, where Sean taught.
For a while the screenplay contained a gay sex scene between Will and Sean in his office, written to see if anybody was actually reading the script during the year Castle Rock would not buy it and they feared it had become poison; nobody noticed until Harvey Weinstein, who told them to get rid of it.
Robin Williams insisted on the L Street bar after being mobbed scouting it and loving the energy, though his scene was not filmed there; he ad-libbed the story about his wife farting, which is why Matt Damon laughed so hard, and son of a bitch, he stole my line, which was supposed to be him reading the note and nodding; Williams was a genius with a complicated reputation because of bad movies.
Robin Williams's character was based on a mix of Damon's mom and Affleck's dad; Gus Van Sant painted the painting in Sean's office; Skyler is based on Damon's ex-girlfriend from Harvard; Damon and Minnie Driver dated from halfway through the movie through the Oscars and had a bad breakup two months later, he apparently dumping her; the hosts decline to discuss the two adjudicating each other on Twitter.
One host's wife called Minnie Driver bad, the reason the movie has not aged as well, and did not believe the relationship; the hosts disagree and think she is really good, though she rightfully did not become the huge star people expected; another host's wife came in for the middle and said the two have no chemistry even after hearing they dated a year in real life.
The hosts feel they are in love at that table; on a very small sample size women may see no chemistry where men do; the knick-knack store googly glasses moment, the Magic 8 ball scene with her NBA jokes, the organic chemistry scene and the piano speech all argue they are in love or amazing performers; she has not been in many movies, unlike a Gwyneth Paltrow with a 20-year history that would color it; one host claims she won the Oscar for this (she was in fact nominated), as evidence people felt that way at the time.
One more research bit: in the original script Will and Skylar leave town together; through a friend of the Affleck family Ben and Matt met Terrence Malick, who had read it and said Will should chase her, she is gone and he has to go find her, so Malick is the reason for the ending, one of many lucky notes and ad-libs that pushed the movie up levels.
Why did Rob Reiner, William Goldman and Terrence Malick want to help two unfamous guys when people struggle in Hollywood for 25 years, and this is the only movie Harvey Weinstein did not chop up as he saw fit; they had some success already, unlike Jon Favreau and Vince Vaughn, though Vaughn was in Rudy as Jamie O'Hara; the only guess is that people sensed they were headed somewhere and wanted to be thanked.
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.
Robin Williams's Boston accent; Matt Damon's frosted tips; the Miramax logo in the opening credits; Will's breakup with Skylar; the screenplay Oscar win over Boogie Nights; the length, especially the two long jokes when Skylar meets Will's friends
Robin Williams's Boston accent is not great and gets a little New York, though some hosts have no ear for it and thought they were all fine; one host says his own accent is gone and only comes out when drunk.
Asked who has the best on-screen Boston accent, the answer is Matt Damon's Will Hunting, the gold standard in the history of movies, better than Wahlberg in The Departed, because the attitude, being ready to fight at all times, is half of it and Damon figured that out more than anyone.
Matt Damon's hair has not aged well; he has talked about regretting the frosted tips and would probably spend money to CGI it away; one host had the same haircut without the tips and thinks it belongs to the mid nineties.
The Miramax logo in the opening credits; Will's breakup with Skylar, I don't love you, has not so much aged badly as remained a rough, physical three minutes that is hard to watch.
Good Will Hunting winning Best Screenplay over Boogie Nights: both are Oscar-worthy with a hundred memorable lines and great characterization, something has to win, and one host prefers Boogie Nights as a movie but calls it close and says this movie holds up.
Asked to choose for the Oscar between Robin Williams and Robert Forster in Jackie Brown, the answer is that the Forster performance is amazing, Jackie Brown is really great, and this is not even the number one movie to have given Robin Williams an Oscar for. — Sean Fennessey
Films Williams should have won for are then thrown out, apparently by more than one voice: Dead Poets, Fisher King, Garp, Good Morning Vietnam, all those movies.
It is long: from a rewatchable standpoint, when Skylar meets Will's buddies and the two long jokes come, you know the jokes after 50 viewings and it drags.
That is a great Skylar scene and there is not enough of her; the great part is not the joke but watching everybody else, the awkwardness, realizing this is the woman he is going to marry, the see-about-a-girl scene playing out in real time with the friends. — Shea Serrano
Others agree it is a necessary scene that only gets a little slow in a movie of about 2:05; Casey Affleck needling Ben back and forth is loved, as are scenes of people talking in bars and diners, and bombed out of his tree has been quoted for 20 years; the alternate jokes on YouTube were all funny; Damon's long barn story in Saving Private Ryan is called the worst part of that movie, though it is supposed to be bad because the guy is a dipshit.
The friendship and the interpersonal relationships; Damon's performance; the two Elliot Smith songs; Casey Affleck's I Hate LA shirt; the Boston accents other than Robin Williams's; the 'how about them apples' scene; the ending; Robin Williams's and Ben Affleck's clothes; the dialogue
The friendship, since this is really a buddies movie about the bonds of friends; Damon is great and it is hard to believe he did not win the Oscar over Jack Nicholson in As Good As It Gets, a two-person category that year with Duvall for The Apostle, Peter Fonda and Dustin Hoffman for Wag the Dog; As Good As It Gets won Best Actor and Best Actress for Helen Hunt while Titanic won Best Picture, and everybody was fine with it when Jim Brooks was still one of the ten most important writer-directors.
The two Elliot Smith songs, Between the Bars and Miss Misery, one still not available on iTunes; his life went into a tailspin after the famous Academy Awards performance in the white suit where he seemed delicate and out of place, and the anecdote that he told anyone trash-talking Celine Dion to shut their mouth because she chilled him out before he went on.
Casey Affleck's I Hate LA shirt in the baseball scene, which one host owned as a kid and whose son is a year from growing into; the Boston accents are spectacular except Robin Williams, and Cole Hauser's is a little iffy in spots but he seems and looks like he is from Boston and carries the fuck-you attitude of the character.
The how-about-them-apples scene has aged incredibly, with the great ending and the callback you always forget is coming; Robin Williams's cardigans and things that don't match make him look like a widower who shops at Goodwill but still has some authority, and Affleck's clothes seem a little more expensive than they were, trying to look classier.
The interpersonal relationships between Damon and Affleck and Damon and Williams could be put in a movie from 1940 or 2018 and would still play.
The friendships are the easiest answer, mainly because of everything that happened afterward, so they are always connected forever; a case could be made for the how-about-them-apples scene, which people still say today and laugh at every time. — Shea Serrano
The apples line was apparently taken from Chinatown, the line Jack Nicholson has in that movie, so maybe Robert Towne wrote Good Will Hunting; I Swallowed a Bug, which Casey Affleck ad-libbed, was taken from Apocalypse Now; the dialogue has aged best because every line was on the tip of the tongue on rewatch, 60 lines recited while watching, which is unique and a testament to them sticking to their guns about their script.
You can understand why people suspected a Goldman rewrite because the movie is so obviously the sum of their love of movies: the playground fight is Mean Streets watched a thousand times, with Ordinary People and early Scorsese elsewhere; that Damon and Affleck stayed friends adds to it, this being their proxy movie.
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.
