Rewatchables Reference

• Bill (winner): The Affleck construction monologue – 'In 20 years if you're still living here, coming over to my house watching the Patriots, working construction, I'll fucking kill you.' Also: the last 30 minutes is 'out of control' – Skylar leaves for LA, construction scene, Lambeau vs. Sean, 'It's not your fault,' and then 'see about a girl.'
• Also discussed: The playground fight scene with Baker Street by Gerry Rafferty (Russillo confused by the music choice), the Harvard bar scene with ponytail guy ('Russillo's dream encounter in 1997'), Will's first meeting with Sean ('Maybe you married the wrong woman – watch it there, chief'), the Boston Common monologue, the 'do you know how easy this is for me?' scene, the farewell therapy scene, and Cole Hauser's 'good car, good engine' moment.
• Sean: Affleck's fake job interview at McNeil ('might be the funniest full scene'), and the two jokes scene – Uncle Marty stealing the cruiser and Minnie Driver's Irish couple joke.
• Russillo: The first kiss with Skylar – 'one of the most natural, cool, non-forced moments. The relationship is so believable.'
• CR: Will's first therapy scene – the art analysis. Also the breakup scene where 'it really feels like he's actually breaking up with her.'

• Bill: Young Damon and Affleck with their whole careers in front of them.
• CR: No Internet – 'Will Hunting doesn't spend all his time on Red Sox Reddit shit-talking Mo Vaughn.'
• Sean: Payphones and the convenience of saying you forgot someone's number.
• Russillo: The diversity of the cast. 'I don't know in 2025 what...' Sean: 'There's Irish and Italian guys in this movie.'

• Bill: Giving someone a Dunkin' Donuts coffee after picking them up from jail. Affleck's late-90s DVD commentary ('he's just on one the entire time'). The therapist scenes. George Plimpton – 'I don't care if you puff from the rough.' The girl at the bar calling Chucky's dick an 'Irish Curse' and a 'Tootsie Roll.'
• CR: Will explaining how jokes work to Robin Williams. Will's art criticism – 'You're one step away from cutting your fucking ear off.' The formation of the friend group – 'The Beatles right there.'
• Sean: Matt and Ben Industries as an iconic duo for 30 years. Robin Williams's conversion from comedy person to iconic actor – this is the movie that cements it.
• Russillo: The Oscar acceptance speech – 'looks like security's supposed to come over and be like, who are you guys?' Boston accents becoming a thing because of this movie. Also Lambeau hitting on college students – 'What the fuck?'

• CR: Tom the graduate assistant – 'gives absolutely nothing in this movie, no emotion. Complete Hannibal Lecter the entire time.'
• Russillo: 'That car doesn't make it past Springfield.'
• Bill: The Game 6 World Series ticket – 'his friends would have fought him' for giving it up.
• Sean: Are we sure Doctor Sean McGuire is a good therapist? 'Commits physical violence during a session. Has no considerable scientific psychological point of view whatsoever. Clearly a shitty college professor – nobody in that class is paying attention.'

• Bill: Harvey Weinstein being the hero of the movie getting made. Sean: 'The two heroes of this movie are Mel Gibson and Harvey Weinstein.' Also: Damon's frosted tips hair.
• CR: Lambeau not having heard of Ted Kaczynski in 1996. Will punching the drywall over Skylar's head. Pre-Jason Bourne fighting choreography from Damon.
• Bill: Lambeau hitting on college students in multiple scenes and then calling Minnie Driver's character – she hangs up and calls him a 'freak.'
• Russillo: 'It's not your fault' becoming overused for a decade by every friend group. Also 'math is erotic.'

• CR: Will is the same as Clark at the Harvard bar – he goes into Robin Williams's office and starts kicking Howard Zinn shit at a guy who actually went to Vietnam, just regurgitating what he read in Chomsky. 'Will is no better than Clark.'
• Sean: 'Is it possible that the midnight-run-esque NSA thriller they wanted this to be could have been better?' Damon did star in 'The Bourne Identity' and it was awesome.
• Russillo: 'There's no way it works when he gets to LA. He's going to hit everybody. His smart powers nobody's going to give a shit about.'
• Bill: Damon's accent in this is the best Boston accent ever by a star in a movie.

• Michael Mann shot a full day of screen test footage and wanted Mexican car thieves in the movie. Damon and Affleck explained that wouldn't feel like Boston. Bill: 'Title would have been Goodwill Haunted.'
• Mel Gibson developed it for a few months, then Damon asked him to let it go because they were aging out of the parts. Gibson agreed.
• Kevin Smith declined to direct: 'I wouldn't dare direct this movie.' Ben Stiller also declined.
• Castle Rock wanted Leonardo DiCaprio and Brad Pitt to star instead of Damon and Affleck.

All: Ponytail guy Clark, played by Scott William Winters. 'Ends up in Oz as Ryan O'Reilly's brother.' Bill: 'Just an all-time that guy.'

• Bill's nominees: Carmine ('you might remember him from juvie'), the Boston girl who made fun of Chucky's Tootsie Roll, George Plimpton. Bill's winner: Cole Hauser – 'you can see the seeds of someday this guy's going to lead Yellowstone.'
• Sean nominated: Jimmy Flynn as the judge. 'He's just doing 'JFK' as a judge.' Flynn was a real local guy.
• Russillo: Cole Hauser deserves it because 'he didn't try to keep up with three local guys. He just knew. And then he was named sexiest man alive 25 years later.'

Director: David Fincher – Bill: 'Don't do The Game, do this instead.' Tony Scott was also discussed.

• Will's address: 357 Q Street 3D in Southie.
• Damon started writing the movie in a playwriting class at Harvard as a 40-page play script, then developed it with Affleck over five years.
• Cambridge scenes filmed at the Bow and Arrow, the Tasty, and Au Bon Pain. A lot of interior shots were sadly filmed in Toronto.
• Skylar is named after Damon's college girlfriend who left him for Lars Ulrich, the Metallica drummer. CR: 'I did spend quite a lot of time on metal websites from 1998 to 2000 trying to track that relationship.'
• Affleck ad-libbed about half his lines. The script would just say things like 'Morgan comes downstairs' and he'd improvise coming down with a baseball glove pretending he'd been jerking off into it.
• Gus Van Sant painted the painting that Will critiques in therapy.
• When filming the Boston Common scene, 3,000 people were watching just off camera.

• Sean: Gus Van Sant – this is the most mainstream thing he's ever done.
• Russillo: Bunker Hill Community College. Also Minnie Driver (Oscar nominated, Grosse Pointe Blank same era). Also accents in movies.
• Bill: L Street Tavern. Math movies (this vs. Pi vs. A Beautiful Mind). Boston Common. The Mass Pike. Cheap track suits. Miramax (or maybe Shakespeare in Love the next year).
• CR: Stellan Skarsgard – but he's also great in Andor, Breaking the Waves, 'Ronin', and Dune Part 2.

Bill: Harvard ponytail guy Clark – 'playing him as Freddie from Talented Mr. Ripley.' CR: 'Or his character from 'Scent of a Woman'.' Everyone was down with this.

• Bill: Nobody else in Lambeau's MIT class could solve the math problem – his whole plan was 'create this problem, put it on a chalkboard, make everyone feel like shit, and then try to fuck them later.' Also: the walk from Bunker Hill CC to the Common is a 10-minute cab ride. And at the end, they gave Will a car and then Chucky pulls up the next day to pick him up – he has a car!
• CR: Will pitching at the batting cages – 'If this is Boston, aren't there a bunch of guys like get the fuck out of the way, I'm trying to hit?' Also: Skylar's 'I should be in the NBA' comment would have set Will off about Rick Pitino and Antoine Walker.
• Sean: By 1997, wouldn't Will just be a hacker making millions? 'He's the smartest guy in the world and he's broke.'
• Russillo: The car wouldn't make it past Springfield. 'Those three guys chipping in to buy a car for the only guy about to make 80 grand a year.' Cole Hauser's character being named Bill – couldn't they have gone with Murph or Fitzy?

• Bill: 30 years later sequel like the 'Before Sunrise'/Sunset/Midnight series – catch up with Will Hunting in his mid-50s. CR's version: 'He's still a janitor in the Midwest and they're all looking for him.'
• Russillo: 'I know what's already happened to the other three. But I cannot express how much Will is going to hate going out in Santa Monica.'

• CR: Chris Collinsworth calling the breakup: 'Oh, Mike, he's only breaking up with Skylar because of the generational trauma. Don Shula has told me you got to love yourself before you love somebody else.' Then as Skylar's crying, the Fox NFL injury jazz plays.
• Sean: Daniel Plainview as Dr. Sean McGuire reading the Boston Common monologue in Daniel Day-Lewis's voice.
• Bill: Tony Romo calling the ending – 'He's got to see about a girl, Jim. He's gonna see about her.' Also: Felger and Maz disparaging Will's math credentials – 'He got lucky at a chalkboard in the hallway with nobody looking. Can you do it every time, Tony? This is regular season math only.'

• CR: Robin Williams – 'pretty fine with him getting the Oscar.'
• Sean and Bill: Damon.
• Russillo: Elliott Smith for Best Original Song.

• Bill: Chucky or Jem – better Boston buddy sidekick? Russillo: 'Chucky. Jem's more fun, but Chucky.' Also: what if Affleck and Damon switched parts? CR: 'Good, but nowhere near what we get.' Sean: 'Damon is surprisingly good at playing dumb.'
• CR: What happens if this movie is set after 2004 and after the Red Sox win?

Bill: The painting would be interesting. NOT the glove. CR: Robin Williams's Red Sox jacket.

• Bill: 'You could be one of the smartest people alive and still not know a damn thing about life.' Also: bet on yourself (Damon/Affleck). Don't answer yes when someone asks if you like apples.
• Russillo: 'It's not your fault – but sometimes it is.'

• CR: Air – to bookend the Damon/Affleck story.
• Sean: 'The Martian' – 'Matt Damon being a genius.'
• Russillo: 'Armageddon' – 'to give Ben a little more chance to shine.'
• Bill: 'The Town' – Affleck's the star, back in Boston, back in Charlestown.

• Sean: 'I think it's a rare case where it has to be two people – Matt and Ben both win.'
• Bill agrees: 'We always say it can't be two people. I don't know how this can be not the two of them.' When you watch the Oscars speech, 'they fucking did it. It took them five years. They made it happen.'
• Russillo: 'I can't imagine what that feeling would be like to be in your 20s, have this idea, pursue it when everybody's telling you it's not going to work, and then you're sitting there holding an award for best original screenplay and then back it up with three decades of work.'