Good Will Hunting The Rewatchables
Good Will Hunting

Probably Unanswerable Questions

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?

In the discussion (16)
Approx. transcript time · 01:20:25Read transcript
  • 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.
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