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THE REWATCHABLES · January 25, 2018

Good Will Hunting

A 1997 drama / romance directed by Gus Van Sant, covered in the complete Rewatchables archive.

DramaRomance1990sDirected by Gus Van Sant
Overall episode#23Source sheet order
Movie year19971990s
Tomatometer97%Critics’ score
Metacritic71View score
Roger Ebert3/4Original star rating
DirectorGus Van SantDrama / Romance

FROM THE CONVERSATION

What they said about the movie

The episode treats Good Will Hunting as a quintessential rewatchable: a hugely quotable Boston movie about friendship, mentorship, and emotional breakthrough, while also noting the Harvey Weinstein/Miramax shadow over its legacy. The panel mostly praises the performances, writing, and ending, with some debate about the Skylar relationship, the Red Sox ticket scene, and whether the movie is a little long.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01The movie is packed with quotable dialogue and scenes that linger in memory after dozens of rewatches. Opening minutes
  2. 02The Damon/Affleck/Robin Williams performances create a strong emotional and comic rhythm that keeps the movie engaging. About 32 min
  3. 03The ending is considered especially strong as a late-in-the-movie rewatchable stretch. About 32 min
  4. 04Boston-specific details and accents make the movie feel like a regional classic. About 40 min

WHAT DID NOT WORK

Their main criticisms

  1. moderateThe Harvey Weinstein/Miramax legacy creates a shadow over the movie when revisiting it. Opening minutes
  2. minorThe movie is a bit too long, especially in the bar/meeting scenes. About 48 min
  3. minorRobin Williams's Boston accent is not great. About 40 min
  4. moderateThe NSA recruitment thread feels illogical and leftover from an earlier version of the script. About 48 min

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Ponytail/Clark confrontation

The bar confrontation with Clark sets the movie in motion and showcases the ensemble's charm, humor, and tension.

About 24 min
Favorite

Pudge Fisk story

Sean and Bill especially praise the Red Sox anecdote as a perfect blend of comedy, acting, and emotional breakthrough.

About 24 min
Favorite

'It's not your fault' scene

The emotional hug between Sean and Will is treated as the film's signature catharsis, though later they note some viewers find it broad.

About 24 min
Favorite

'Go see about a girl' breakup and departure

The breakup with Skylar and Will's decision to drive after her is debated as romantic, cruel, and defining.

About 24 min
Favorite

'How do you like them apples?' scene

The insult/reveal scene is cited as one of the movie's most famous and durable lines.

About 40 min
Favorite

Chucky's car monologue

Chucky's 'best part of my day' speech is held up as one of the movie's great friendship scenes.

About 32 min
mixed

Skylar meets the friends at the bar

The long bar scene is seen as necessary and funny, but also the movie's one noticeably slower stretch.

About 48 min

WHERE THEY DISAGREED

The biggest debates

They partly agreed About 24 min

Does the Skylar breakup scene show real chemistry or not?

Bill Simmons

He believes the relationship is believable and that Skylar understands Will's emotional damage.

Shea Serrano

He thinks the breakup scene is harsh and that Skylar probably never fully gets over it.

Sean Fennessey

He also questions whether the scene is as romantic as people assume.

They partly agreed About 1:12

Did Robin Williams or Matt Damon win the movie?

Sean Fennessey

Williams wins because the performance is irreplaceable and powerful.

Chris Ryan

Williams wins because he dominates every scene.

Shea Serrano

Damon wins because he carries more of the movie's acting burden.

Bill Simmons

He sides with Damon in the end, then explains why Williams is still essential.

They left it as a friendly argument About 24 min

Is Will a real Red Sox die-hard if he gives up Game 6 tickets?

Bill Simmons

He doubts a true Red Sox fan would ever skip that game.

Sean Fennessey

He argues the scene works because Will is more artsy than hardcore sports-obsessed.

Chris Ryan

He accepts the emotional logic of the scene rather than the sports logic.

No final agreement About 48 min

Who should have won the screenplay Oscar: Good Will Hunting or Boogie Nights?

Bill Simmons

He thinks both are all-time scripts and is uneasy about the outcome.

Sean Fennessey

He leans toward Good Will Hunting in the category comparison.

12 People discussedActors, directors, writers, and producers
criticalHarvey WeinsteinBill Simmons: Discussed as the Miramax figure who helped get the movie made, but whose later legacy casts a shadow over it. Opening minutes very favorableMatt DamonBill Simmons: Praised as irreplaceable as Will Hunting and the actor who had to do the most in the film. About 32 min favorableBen AffleckSean Fennessey: Praised as charming and funny as Chucky, and discussed as a future star who later pursued different career paths. About 24 min very favorableRobin WilliamsSean Fennessey: Lauded as the movie's emotional center and a likely Oscar winner whose performance is hard to replace. About 24 min favorableMinnie DriverBill Simmons: Praised as excellent and funny as Skylar, though the panel notes some viewers see her chemistry with Damon differently. About 32 min neutralGus Van SantBill Simmons: Mentioned as the director who was part of the movie's final form and Oscar run. About 8 min mixedWilliam GoldmanBill Simmons: Discussed as the famous screenwriter who supposedly rewrote the script, though the panel leans toward believing he only gave notes. Opening minutes favorableStellan SkarsgårdChris Ryan: Praised as creepy but effective as Professor Lambeau, the entitled academic figure. About 56 min favorableCasey AffleckBill Simmons: Highlighted as a heat-check supporting player with several of the movie's funniest lines. About 56 min favorableCole HauserShea Serrano: Admired as intimidating, funny, and very Boston in the small role of Clark. About 56 min favorableElliott SmithSean Fennessey: Mentioned as the artist whose music deepens the film's emotional impact, especially in the ending. About 40 min
neutralTerrence MalickBill Simmons: Cited as an unexpected source of a script note that helped shape the ending. About 48 min
7 Conversation takesSpeakers shown only where the transcript identifies them
Bill SimmonsMixed

Good Will Hunting as a legacy piece under a Weinstein shadow

Says the movie still works for him, but the Miramax/Weinstein context now has to be acknowledged.

Opening minutes
Bill SimmonsLoved it

the Red Sox ticket / see about a girl scene

Calls it one of the movie's great emotional turns and a defining rewatchable moment.

About 16 min
Bill SimmonsLoved it

the park bench / 'it's not your fault' scene

Treats the scene as central to the film's emotional payoff, despite later criticism about overstatement.

About 24 min
Bill SimmonsLoved it

Matt Damon as Will Hunting

Argues Damon should have won the Oscar and that nobody else could have played Will.

About 32 min
Bill SimmonsLoved it

the Pudge Fisk story

Calls this his pick for most rewatchable scene because it combines comedy, performance, and the film's emotional connection.

About 24 min
Bill SimmonsLiked it

Boston authenticity

Says the film is a definitive Boston movie and argues it must be judged as such.

About 56 min
Bill SimmonsLoved it

Robin Williams

Ultimately picks Williams as the actor who won the movie because his performance is irreplaceable and unforgettable.

About 1:12
4 ThemesThe larger ideas in the discussion

Friendship and loyalty

The panel frames the movie as fundamentally about male friendship and the bond between Will and Chucky.

About 40 min

Emotional healing and mentorship

Will's breakthrough with Sean and the idea of being believed in are treated as the film's core emotional engine.

About 24 min

Boston identity

The movie is discussed as a deeply Boston-specific story defined by accents, bars, neighborhoods, and sports culture.

About 40 min

Hollywood miracle story

The film's development history is presented as a classic Hollywood saga involving Castle Rock, Miramax, rewrites, and Oscar campaigns.

Opening minutes
21 Facts and referencesProduction notes and other movies mentioned

Production note

The script originally included a CIA/spy-action second half that was dropped.

Opening minutes

Production note

There was an Oscar smear rumor that William Goldman had rewritten the script, but Goldman denied it.

Opening minutes

Production note

A gay sex scene was reportedly inserted into the script to see whether anyone was actually reading it.

About 48 min

Production note

Terrence Malick suggested the ending where Will chases Skylar instead of leaving with her.

About 48 min

Production note

Robin Williams ad-libbed the line about his wife farting.

About 48 min

Production note

The 'son of a bitch, you stole my line' reaction was also ad-libbed.

About 48 min

Production note

The Pudge Fisk scene used licensed baseball footage and was important to the joke working.

About 24 min

Production note

The park-bench scene became a memorial site after Robin Williams died.

About 48 min

The Rainmaker

Used to explain how Damon got Harvey Weinstein interested in making Good Will Hunting.

Opening minutes

Boogie Nights

Referenced as a movie Bill has seen many times and as a screenplay Oscar comparison.

Opening minutes

Princess Bride

Bill and Chris use it as a joke comparison for 'only two' sports-gal style figures.

About 16 min

The Accountant

Sean jokes that Affleck's later film resembles the originally abandoned spy/action version of Good Will Hunting.

About 8 min

As Good as It Gets

Mentioned as the movie whose acting wins beat Damon and Robin Williams at the Oscars.

About 8 min

Dead Poets Society

Cited in a discussion of Robin Williams's earlier Oscar-caliber performances.

About 8 min

The Departed

Used to compare Boston-movie authenticity and Boston accents.

About 40 min

Finding Forrester

Referenced as a possible spiritual cousin or missed opportunity from Gus Van Sant.

About 1:04

The Town

Used in sequel/speculation and Boston-movie comparison talk.

About 1:20

Spotlight

Used as an example of a Mark Ruffalo 'they knew' overacting-style moment.

About 56 min

Ocean's Eleven

Mentioned in a debate about why Affleck wasn't in the movie and whether that affected career dynamics.

About 1:20

Limitless

Referenced as a film/series concept Shea likes because it involves a smart protagonist solving things.

About 1:12

Goodfellas

Used as a comparison for the National Lampoon film's style in the ad segment.

About 48 min
10 Running jokes and short linesRecurring bits captured from the conversation

'Would this be better if Michael Mann had made it?'

A recurring joke category raised by the show, quickly converted into a Danny Trejo gag and then abandoned.

About 48 min

Boston authenticity debate

Repeated joking about who is a real Boston sports fan, who would or would not give up a Red Sox ticket, and whether Sean's friends are legitimate fans.

About 16 min

'Mark Ruffalo, they knew' category riff

They spin a fake award category for over-the-top acting and connect it to Ruffalo's Spotlight outburst.

About 56 min

Future sequel brainstorming

They invent multiple absurd Good Will Hunting sequels, including a CIA version, prison version, tech-bro version, and Boston-crime version.

About 1:04

Cole Hauser praise loop

The panel repeatedly jokes that Cole Hauser should have become a bigger action villain.

About 56 min

Bill Simmons

“I gotta go see about a girl.”
About 16 min

Bill Simmons

“Our boy's wicked smart.”
About 24 min

Speaker not identified

“It's not your fault.”
About 24 min

Bill Simmons

“How do you like them apples?”
About 40 min

Chris Ryan

“Do you know how easy this is for me?”
About 40 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where Good Will Hunting is available…

WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before Good Will Hunting, and three to watch next.

Finding six movies…Three to watch first and three to watch next.
Includes a Rewatchables episodePosters from TMDB.

ON THE MIC

4 voices on this episode

Bill Simmons headshotBill SimmonsThe Rewatchables
Chris Ryan headshotChris RyanThe Rewatchables
Sean Fennessey headshotSean FennesseyThe Rewatchables
Shea Serrano headshotShea SerranoThe Rewatchables

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