Home/Episodes/Good Will Hunting
‘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 · ▶ Listen on Spotify
Categories
Hall of Fame Plaque
Bill SimmonsThe bar scene where Will intellectually destroys Clark, leading to the 'do you like apples' moment▶ 37:36
Butch's Girlfriend Award
Bill SimmonsMultiple 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▶ 1:10:10
Chris RyanTom the graduate assistant character who gives absolutely nothing and shows no emotion throughout the movie▶ 1:10:15
Ryen RussilloWill'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▶ 1:10:52
Sean FennesseyWished 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▶ 1:12:16
Stephen A. Smith Hottest Take Award
Bill SimmonsThis is the best Boston accent ever by Damon in a movie - everything he does has the right level of anger to it▶ 1:18:22
Chris RyanWill 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▶ 1:16:51
Ryen RussilloThere'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▶ 1:16:52
Sean FennesseyThe Midnight Run-esque NSA thriller version they originally wanted could have actually been better than the real Good Will Hunting▶ 1:16:22
Casting What-Ifs
Chris RyanProvided context on Kevin Smith and Ben Stiller declining to direct, but no specific casting pick▶ 1:19:34
Sequel/Prequel/Limited Series/Remake
Bill SimmonsYes, would be interested in catching up with Will Hunting in his mid-50s, 30 years later▶ 1:39:07
Ryen RussilloNo interest in catching up with these characters since we already know what happened to the other three▶ 1:39:34
Is This Movie Better With
Bill SimmonsTony 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▶ 1:42:07
Chris RyanChris Collinsworth providing commentary during Will and Skylar's breakup about generational trauma and self-loathing, with Fox NFL injury jazz playing as Skylar cries▶ 1:40:36
Sean FennesseyDaniel Day-Lewis — Daniel Plainview as Sean McGuire, delivering the art speech in Plainview's voice and style▶ 1:41:31
Probably Unanswerable Questions
Bill SimmonsSwitching Affleck and Damon wouldn't be as good but would be an interesting thought experiment - feels weird but Affleck can do smart roles▶ 1:45:03
Chris RyanIf 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▶ 1:44:30
Ryen RussilloChucky is the better Boston buddy sidekick - more reliable for renting a house in the Cape▶ 1:44:16
Sean FennesseyDamon is surprisingly good at playing dumb so maybe he could have pulled off Chucky's part▶ 1:44:48
Coach Finstock Life Lesson
Bill SimmonsMultiple 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'▶ 1:47:56
Ryen RussilloAgrees with the 'it's not your fault' lesson but notes that many people think things aren't their fault when they actually are▶ 1:48:03
Sean FennesseyChallenges the 'it's not your fault' lesson by pointing out that Matt Damon's character picked a fight with Carmine, which was his fault▶ 1:48:08
Who Won the Movie
Bill SimmonsMatt Damon — Agrees with Damon/Affleck for their persistence in making the movie happen over five years despite everyone telling them it wouldn't work▶ 1:49:45
Ryen RussilloMatt 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▶ 1:50:13
Movies Referenced (51)
| Title (year) | Links | Mentions | Mentioned by | First |
|---|---|---|---|---|
| The Departed (2006) | IMDb ↗Lb ↗ | 7 | Ryen Russillo, Chris Ryan, Bill Simmons | ▶ 3:34 |
| Titanic (1997) | IMDb ↗Lb ↗ | 6 | Bill Simmons, Sean Fennessey | ▶ 14:10 |
| As Good as It Gets (1997) | IMDb ↗Lb ↗ | 5 | Bill Simmons, Sean Fennessey, Ryen Russillo | ▶ 14:52 |
| Boogie Nights (1997) | IMDb ↗Lb ↗ | 5 | Bill Simmons, Ryen Russillo, Sean Fennessey | ▶ 14:18 |
| Armageddon (1998) | IMDb ↗Lb ↗ | 3 | Ryen Russillo, Bill Simmons | ▶ 20:18 |
| Chasing Amy (1997) | IMDb ↗Lb ↗ | 3 | Sean Fennessey, Bill Simmons | ▶ 14:41 |
| Shakespeare in Love (1998) | IMDb ↗Lb ↗ | 3 | Bill Simmons, Sean Fennessey | ▶ 24:53 |
| Wicked (2024) | IMDb ↗Lb ↗ | 3 | Bill Simmons | ▶ 38:52 |
| Dazed and Confused (1993) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 6:27 |
| Fargo (1996) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 32:39 |
| Goodfellas (1990) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 43:17 |
| Jackie Brown (1997) | IMDb ↗Lb ↗ | 2 | Sean Fennessey, Bill Simmons | ▶ 14:39 |
Directors Referenced (11)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Ben Affleck | IMDb ↗Lb ↗ | 27 | Bill Simmons, Sean Fennessey, Ryen Russillo | Argo, Gone Girl, The Town | ▶ 5:36 |
| Mel Gibson | IMDb ↗Lb ↗ | 6 | Bill Simmons, Sean Fennessey, Ryen Russillo | Braveheart, Lethal Weapon 3, Conspiracy Theory | ▶ 1:12:40 |
| Francis Ford Coppola | IMDb ↗Lb ↗ | 4 | Sean Fennessey | Apocalypse Now, The Godfather Part II | ▶ 1:00:04 |
| Kevin Smith | IMDb ↗Lb ↗ | 4 | Chris Ryan, Bill Simmons | Clerks, Chasing Amy | ▶ 15:00 |
| Michael Mann | IMDb ↗Lb ↗ | 4 | Ryen Russillo, Chris Ryan | The Insider, Collateral, The Last of the Mohicans | ▶ 24:11 |
| Gus Van Sant | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 43:12 | |
| Paul Thomas Anderson | IMDb ↗Lb ↗ | 2 | Sean Fennessey, Bill Simmons | Punch-Drunk Love, Licorice Pizza, There Will Be Blood | ▶ 14:32 |
| Chris Corner | IMDb ↗Lb ↗ | 1 | Bill Simmons | The Saint, Open Your Eyes | ▶ 3:06 |
| Rob Reiner | IMDb ↗Lb ↗ | 1 | Bill Simmons | This Is Spinal Tap, The Wolf of Wall Street | ▶ 8:13 |
| Sean Penn | IMDb ↗Lb ↗ | 1 | Ryen Russillo | Mystic River, 21 Grams, Dead Man Walking | ▶ 1:05:36 |
| Woody Allen | IMDb ↗Lb ↗ | 1 | Sean Fennessey | Annie Hall | ▶ 25:41 |
Actors Referenced (59)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Matt Damon | IMDb ↗Lb ↗ | 68 | Bill Simmons, Ryen Russillo, Chris Ryan | Good Will Hunting, The Martian, The Departed | ▶ 5:36 |
| Robin Williams | IMDb ↗Lb ↗ | 23 | Bill Simmons, Sean Fennessey, Ryen Russillo | Mrs. Doubtfire | ▶ 14:16 |
| Cole Hauser | IMDb ↗Lb ↗ | 14 | Bill Simmons, Ryen Russillo, Chris Ryan | Dazed and Confused, Good Will Hunting | ▶ 11:49 |
| Jack Nicholson | IMDb ↗Lb ↗ | 12 | Bill Simmons, Sean Fennessey, Chris Ryan | Chinatown, As Good as It Gets, The Departed | ▶ 3:56 |
| Morgan Freeman | IMDb ↗Lb ↗ | 7 | Bill Simmons, Sean Fennessey | Se7en, Driving Miss Daisy, Million Dollar Baby | ▶ 20:38 |
| George Plimpton | IMDb ↗Lb ↗ | 6 | Bill Simmons, Ryen Russillo | Good Will Hunting | ▶ 1:04:05 |
| Minnie Driver | IMDb ↗Lb ↗ | 6 | Bill Simmons, Ryen Russillo, Sean Fennessey | Good Will Hunting | ▶ 23:12 |
| Janelle Cambridge | IMDb ↗Lb ↗ | 5 | Bill Simmons, Ryen Russillo | American Gangster | ▶ 12:32 |
| Amy Poehler | IMDb ↗Lb ↗ | 4 | Sean Fennessey, Chris Ryan, Bill Simmons | Inside Out | ▶ 0:00 |
| Backstreet Boys | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | This Is the End, The Nutty Professor | ▶ 25:14 |
| Castle Rock | IMDb ↗Lb ↗ | 4 | Bill Simmons, Ryen Russillo, Sean Fennessey | ▶ 7:28 | |
| Burt Reynolds | IMDb ↗Lb ↗ | 3 | Bill Simmons, Sean Fennessey | Boogie Nights, Smokey and the Bandit, Striptease | ▶ 28:21 |
Writers Referenced (8)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Harvey Weinstein | IMDb ↗Lb ↗ | 5 | Bill Simmons, Sean Fennessey | Shakespeare in Love, The Hateful Eight | ▶ 8:51 |
| Roger Ebert | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | ▶ 30:09 | |
| William Goldman | IMDb ↗Lb ↗ | 4 | Chris Ryan, Bill Simmons, Ryen Russillo | Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride | ▶ 8:18 |
| James Cameron | IMDb ↗Lb ↗ | 2 | Bill Simmons, Sean Fennessey | Avatar, Aliens, Terminator 2: Judgment Day | ▶ 14:13 |
| Noam Chomsky | IMDb ↗Lb ↗ | 2 | Sean Fennessey, Chris Ryan | ▶ 38:18 | |
| James L. Brooks | IMDb ↗Lb ↗ | 1 | Bill Simmons | Broadcast News, As Good as It Gets, Terms of Endearment | ▶ 26:56 |
| Lawrence Bender | IMDb ↗Lb ↗ | 1 | Chris Ryan | Pulp Fiction, Kill Bill: Vol. 1, Reservoir Dogs | ▶ 15:04 |
| Taylor Sheridan | IMDb ↗Lb ↗ | 1 | Bill Simmons | Hell or High Water, Wind River | ▶ 53:45 |
Cinematographers Referenced (1)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Ryan O'Reilly | IMDb ↗Lb ↗ | 1 | Bill Simmons | The Meg | ▶ 1:20:02 |