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‘Good Will Hunting’ Live From Boston With Bill Simmons, Ryen Russillo, Chris Ryan, and Sean Fennessey

April 1, 2025 · Good Will Hunting (1997) · Drama · Romance · 1:53:40

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Apex Mountain

Ryen Russillo▶ 34:34Bunker Hill Community College

Most Rewatchable Scene

Bill Simmons▶ 35:58The playground fight scene
Bill Simmons▶ 36:29The Harvard Bar scene at the bow and arrow

Hall of Fame Plaque

Bill Simmons▶ 37:36The bar scene where Will intellectually destroys Clark, leading to the 'do you like apples' moment
Chris Ryan▶ 37:42The bar scene with the friend group backing Will against Clark
Ryen Russillo▶ 40:42Discussed the psychological impact and realism of the bar scene confrontation
Sean Fennessey▶ 39:52The bar scene where Will embarrasses Clark intellectually instead of fighting

Den of Thieves Benihana Award

Bill Simmons▶ 1:07:23Boston Common

Butch's Girlfriend Award

Bill Simmons▶ 1:10:10Multiple weak elements including giving up the game six ticket, Damon's frosted tips hair, Gerald Lambeau hitting on college students, and Kelly's takeout reference
Chris Ryan▶ 1:10:15Tom the graduate assistant character who gives absolutely nothing and shows no emotion throughout the movie
Ryen Russillo▶ 1:10:52Will's unrealistic plan to drive cross-country in a broken-down car that wouldn't make it past Springfield, and the friends buying a car for the guy about to make 80k a year
Sean Fennessey▶ 1:12:16Wished the referenced Boston friends (Marky, Ricky, Danny, Terry, etc.) actually existed as characters, and noted Harvey Weinstein and Mel Gibson being heroes of the movie getting made

Is There a Better Title?

Bill Simmons▶ 1:16:20Suggested multiple titles: Wicked Smart, The Janitor
Chris Ryan▶ 1:16:16Good Well Hunted

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 1:18:22This is the best Boston accent ever by Damon in a movie - everything he does has the right level of anger to it
Chris Ryan▶ 1:16:51Will is actually the guy he is making fun of at the Harvard Bar - he's no better than Clark because he's just regurgitating what he read in Chomsky to Robin Williams who actually went to Vietnam
Ryen Russillo▶ 1:16:52There's no way Will's move to L.A. works - he won't fit in, will hate everybody, and nobody will care about his smart powers
Sean Fennessey▶ 1:16:22The Midnight Run-esque NSA thriller version they originally wanted could have actually been better than the real Good Will Hunting

Casting What-Ifs

Bill Simmons▶ 1:21:59Cole Hauser — Cole Hauser for Deon Waiter's Award
Chris Ryan▶ 1:19:34Provided context on Kevin Smith and Ben Stiller declining to direct, but no specific casting pick
Ryen Russillo▶ 1:22:22Cole Hauser — Agrees with Cole Hauser for Deon Waiter's Award
Sean Fennessey▶ 1:22:04Jimmy Flynn — Jimmy Flynn (the judge) for Deon Waiter's Award

Sequel/Prequel/Limited Series/Remake

Bill Simmons▶ 1:39:07Yes, would be interested in catching up with Will Hunting in his mid-50s, 30 years later
Chris Ryan▶ 1:39:17Will is still a janitor in the midwest and they're all looking for him
Ryen Russillo▶ 1:39:34No interest in catching up with these characters since we already know what happened to the other three
Sean Fennessey▶ 1:39:27Will is in UFC choking guys out based on what we saw in the bounce castle

Is This Movie Better With

Bill Simmons▶ 1:42:07Tony Romo — Tony Romo watching the ending going 'he's gonna say better girl Jim, he's gonna say better' and Felger and Maz discussing Will's math credentials skeptically
Chris Ryan▶ 1:40:36Chris Collinsworth providing commentary during Will and Skylar's breakup about generational trauma and self-loathing, with Fox NFL injury jazz playing as Skylar cries
Sean Fennessey▶ 1:41:31Daniel Day-Lewis — Daniel Plainview as Sean McGuire, delivering the art speech in Plainview's voice and style

Just One Oscar

Bill Simmons▶ 1:43:54Matt Damon — Damon (Matt Damon)
Chris Ryan▶ 1:43:42Robin Williams
Ryen Russillo▶ 1:43:49Matt Damon — Damon (Matt Damon)

Probably Unanswerable Questions

Bill Simmons▶ 1:45:03Switching Affleck and Damon wouldn't be as good but would be an interesting thought experiment - feels weird but Affleck can do smart roles
Chris Ryan▶ 1:44:30If Affleck and Damon switched parts, it would be good but nowhere near as effective - Damon has golden boy vulnerability, Affleck is perfect as the happy-go-lucky guy
Ryen Russillo▶ 1:44:16Chucky is the better Boston buddy sidekick - more reliable for renting a house in the Cape
Sean Fennessey▶ 1:44:48Damon is surprisingly good at playing dumb so maybe he could have pulled off Chucky's part

Coach Finstock Life Lesson

Bill Simmons▶ 1:47:56Multiple lessons: 'it's not your fault but sometimes it is', 'bet on yourself' (referencing Damon and Affleck's career move), and 'don't answer yes or no if somebody asked if you like apples'
Ryen Russillo▶ 1:48:03Agrees with the 'it's not your fault' lesson but notes that many people think things aren't their fault when they actually are
Sean Fennessey▶ 1:48:08Challenges the 'it's not your fault' lesson by pointing out that Matt Damon's character picked a fight with Carmine, which was his fault

Best Double Feature

Bill Simmons▶ 1:49:12The Town
Chris Ryan▶ 1:48:48Air
Ryen Russillo▶ 1:49:01Priscilla — Mentioned Priscilla, Armageddon, and The Town as options
Sean Fennessey▶ 1:48:58The Martian

Who Won the Movie

Bill Simmons▶ 1:49:45Matt Damon — Agrees with Damon/Affleck for their persistence in making the movie happen over five years despite everyone telling them it wouldn't work
Chris Ryan▶ 1:49:17Matt Damon — Damon
Ryen Russillo▶ 1:50:13Matt Damon — Supports Damon/Affleck pick, emphasizing the incredible feeling of being in your 20s, having everyone tell you your idea won't work, then proving them all wrong. Notes Robin Williams nails every scene but can't imagine that feeling of vindication

Movies Referenced (54)

The Departed (2006)

7 mentions · Ryen Russillo, Chris Ryan, Bill Simmons▶ 3:34IMDb ↗Lb ↗

Titanic (1997)

6 mentions · Bill Simmons, Sean Fennessey▶ 14:10IMDb ↗Lb ↗

As Good as It Gets (1997)

5 mentions · Bill Simmons, Sean Fennessey, Ryen Russillo▶ 14:52IMDb ↗Lb ↗

Boogie Nights (1997)

5 mentions · Bill Simmons, Ryen Russillo, Sean Fennessey▶ 14:18IMDb ↗Lb ↗

The Town (2010)

5 mentions · Bill Simmons, Ryen Russillo▶ 3:23IMDb ↗Lb ↗

Armageddon (1998)

3 mentions · Ryen Russillo, Bill Simmons▶ 20:18IMDb ↗Lb ↗

Chasing Amy (1997)

3 mentions · Sean Fennessey, Bill Simmons▶ 14:41IMDb ↗Lb ↗

Rocky (1976)

3 mentions · Bill Simmons, Chris Ryan▶ 5:51IMDb ↗Lb ↗

School Ties (1992)

3 mentions · Bill Simmons▶ 6:25IMDb ↗Lb ↗

Shakespeare in Love (1998)

3 mentions · Bill Simmons, Sean Fennessey▶ 24:53IMDb ↗Lb ↗

Wicked (2024)

3 mentions · Bill Simmons▶ 38:52IMDb ↗Lb ↗

Dazed and Confused (1993)

2 mentions · Bill Simmons▶ 6:27IMDb ↗Lb ↗

Directors Referenced (11)

Ben Affleck

27 mentions · Bill Simmons, Sean Fennessey, Ryen Russillo · Known for Argo, Gone Girl, The Town▶ 5:36IMDb ↗Lb ↗

Mel Gibson

6 mentions · Bill Simmons, Sean Fennessey, Ryen Russillo · Known for Braveheart, Conspiracy Theory▶ 1:12:40IMDb ↗Lb ↗

Francis Ford Coppola

4 mentions · Sean Fennessey · Known for Apocalypse Now, The Godfather Part II▶ 1:00:04IMDb ↗Lb ↗

Kevin Smith

4 mentions · Chris Ryan, Bill Simmons · Known for Clerks, Chasing Amy▶ 15:00IMDb ↗Lb ↗

Michael Mann

4 mentions · Ryen Russillo, Chris Ryan · Known for The Insider, Collateral, The Last of the Mohicans▶ 24:11IMDb ↗Lb ↗

Gus Van Sant

2 mentions · Bill Simmons, Chris Ryan · Known for Drugstore Cowboy▶ 43:12IMDb ↗Lb ↗

Paul Thomas Anderson

2 mentions · Sean Fennessey, Bill Simmons · Known for Punch-Drunk Love, Licorice Pizza, There Will Be Blood▶ 14:32IMDb ↗Lb ↗

Chris Corner

1 mentions · Bill Simmons · Known for The Saint, Open Your Eyes▶ 3:06IMDb ↗Lb ↗

Rob Reiner

1 mentions · Bill Simmons · Known for This Is Spinal Tap, The Wolf of Wall Street▶ 8:13IMDb ↗Lb ↗

Sean Penn

1 mentions · Ryen Russillo · Known for Mystic River, 21 Grams, Dead Man Walking▶ 1:05:36IMDb ↗Lb ↗

Woody Allen

1 mentions · Sean Fennessey · Known for Annie Hall, Deconstructing Harry▶ 25:41IMDb ↗Lb ↗

Actors Referenced (58)

Matt Damon

68 mentions · Bill Simmons, Ryen Russillo, Chris Ryan · Known for Good Will Hunting, The Martian, The Departed▶ 5:36IMDb ↗Lb ↗

Robin Williams

23 mentions · Bill Simmons, Sean Fennessey, Ryen Russillo · Known for Mrs. Doubtfire▶ 14:16IMDb ↗Lb ↗

Cole Hauser

14 mentions · Bill Simmons, Ryen Russillo, Chris Ryan · Known for Dazed and Confused, Good Will Hunting▶ 11:49IMDb ↗Lb ↗

Jack Nicholson

12 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Chinatown, As Good as It Gets, The Departed▶ 3:56IMDb ↗Lb ↗

Morgan Freeman

7 mentions · Bill Simmons, Sean Fennessey · Known for Se7en, Driving Miss Daisy, Million Dollar Baby▶ 20:38IMDb ↗Lb ↗

George Plimpton

6 mentions · Bill Simmons, Ryen Russillo · Known for Good Will Hunting, Just Cause▶ 1:04:05IMDb ↗Lb ↗

Minnie Driver

6 mentions · Bill Simmons, Ryen Russillo, Sean Fennessey · Known for Good Will Hunting▶ 23:12IMDb ↗Lb ↗

Janelle Cambridge

5 mentions · Bill Simmons, Ryen Russillo · Known for American Gangster▶ 12:32IMDb ↗Lb ↗

Amy Poehler

4 mentions · Sean Fennessey, Chris Ryan, Bill Simmons · Known for Inside Out▶ 0:00IMDb ↗Lb ↗

Backstreet Boys

4 mentions · Bill Simmons, Chris Ryan · Known for This Is the End, The Nutty Professor▶ 25:14IMDb ↗Lb ↗

Castle Rock

4 mentions · Bill Simmons, Ryen Russillo, Sean Fennessey▶ 7:28IMDb ↗Lb ↗

Burt Reynolds

3 mentions · Bill Simmons, Sean Fennessey · Known for Boogie Nights, Smokey and the Bandit, Striptease▶ 28:21IMDb ↗Lb ↗

Writers Referenced (7)

Harvey Weinstein

5 mentions · Bill Simmons, Sean Fennessey · Known for Shakespeare in Love, The Hateful Eight▶ 8:51IMDb ↗Lb ↗

Roger Ebert

4 mentions · Bill Simmons, Chris Ryan▶ 30:09IMDb ↗Lb ↗

William Goldman

4 mentions · Chris Ryan, Bill Simmons, Ryen Russillo · Known for Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 8:18IMDb ↗Lb ↗

James Cameron

2 mentions · Bill Simmons, Sean Fennessey · Known for Avatar, Aliens, Terminator 2: Judgment Day▶ 14:13IMDb ↗Lb ↗

Noam Chomsky

2 mentions · Sean Fennessey, Chris Ryan▶ 38:18IMDb ↗Lb ↗

Lawrence Bender

1 mentions · Chris Ryan · Known for Pulp Fiction, Kill Bill: Vol. 1, Reservoir Dogs▶ 15:04IMDb ↗Lb ↗

Taylor Sheridan

1 mentions · Bill Simmons · Known for Hell or High Water, Wind River▶ 53:45IMDb ↗Lb ↗