Joaquin Phoenix, then credited as Leaf, gives a performance that forecasts an Oscar winner, especially when his face breaks while asking his father if he can live with him. — Bill Simmons
One participant did not realize the actor was the boy from Parenthood until after Gladiator, when a sister pointed it out. — Van Lathan
A Kanye West lyric from Gone about a new wife and “now you’re Jennifer Aniston” is said to borrow from the film’s line about a new wife and family. — Van Lathan
Gil’s thumb trick still delights small children. — Bill Simmons
The grandmother inhaling helium is favored, as any helium scene is funny. — Bill Simmons
Per the research, there was a rivalry in which DiCaprio sought the Garry role, Phoenix got it, and the two competed for parts, with Phoenix measuring himself against DiCaprio. — Bill Simmons
Garry’s chaotic room is praised as a horror show compared with a real teenager’s room. — Bill Simmons
The boyfriend character as every parent’s nightmare who turns out decent is a favored concept. — Bill Simmons
The nude-photo discovery reportedly happened to producer Brian Grazer; developing such photos in the 1980s is joked about. — Bill Simmons
The Cure's Boys Don't Cry poster in Julie's room is appreciated. — Bill Simmons
Kevin’s tense face became a recurring reference in an early sports column, seen in a head coach during the Super Bowl and in LeBron James. — Bill Simmons
Harley Jane Kozak, also Helen in When Harry Met Sally, is appreciated as an actor who never quite broke through. — Bill Simmons
The film’s candid treatment of money, including Larry’s debts, Gil’s worries about private school, and summer-school pay funding a vacation, is more relatable than shows where money is no object. — Chris Ryan
The car sex-act gag is raised but deferred to Apex Mountain.
A 10-episode Netflix series including the CIA half, cast with Elgort as Chucky, Chalamet as Will, Jon Hamm as the therapist and Tessa Thompson as Skylar; a Black Good Will Hunting is Stomp the Yard
Asked whether he would watch a 10-episode Netflix series remake with the second half of the script and the CIA wrinkle, the answer is 100%, having watched the Limitless series. — Shea Serrano
Anyone smarter than everyone else figuring things out is loved; although remaking rewatchable movies is usually avoided, the obvious casting is staring them in the face: Elgort as Affleck and Chalamet as Damon, who went to the same high school, love the Knicks and are playing this out on Instagram, Elgort the empty-headed pretty boy and Chalamet the nervy energy; the first three episodes are the movie before the CIA stuff.
For the therapist, Ruffalo, Jeff Bridges, Russell Crowe and Jon Hamm are floated, Hamm with a beard, older, available, with Affleck ties and ready to go back to Boston; Tessa Thompson as Minnie; Ringer Films is jokingly producing the 10-episode adaptation.
Gus Van Sant did a version of this with Finding Forrester, a movie with issues that should have been good and was a missed opportunity, though it invented the modern internet with you're the man now, dog.
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.
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.
