Home/Episodes/The Departed

“The Re-Departed” With Bill Simmons, Chris Ryan, and Sean Fennessey

October 5, 2021 · The Departed (2006) · Crime · Drama · Thriller · 1:57:28 · ▶ Listen on Spotify

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Apex Mountain

Bill SimmonsMartin ScorseseThis movie redefined Scorsese's career success and led to bigger budgets like HBO's blank check for Vinyl▶ 35:14
Sean FennesseyMartin ScorseseYes, this completely redefined Scorsese as a successful Hollywood filmmaker since he made very few hits before this▶ 35:22

Most Rewatchable Scene

Bill SimmonsWahlberg fucking with Leo (the Dignam interrogation scene), the cranberry juice scene with Ray Winstone, Damon's first date with Vera Farmiga (borderline), and Leo meets Costello in the bar▶ 36:58
Chris RyanAgreed with the Wahlberg/Leo scene and praised Leo meets Costello in the bar as one of his favorite character introductions▶ 41:57
Sean FennesseyAgreed with the cranberry juice scene and discussed the Leo/Costello bar meeting dynamics▶ 40:53

Casting What-Ifs

Bill SimmonsAl PacinoPresents alternate cast (Leo, Pitt, Pacino, Liotta, De Niro, Mel Gibson, RZA) and says 'I think I like that cast more' but acknowledges trade-offs like losing Nicholson's physicality for Pacino▶ 1:18:38
Chris RyanMatt DamonPrefers actual cast - thinks Damon is 'way better choice' than Pitt, questions if Pacino works as Irish mob boss, suggests alternative cast should be made as separate movie▶ 1:15:55
Sean FennesseyAlec BaldwinPrefers actual cast - would rather have Wahlberg over Liotta, '100 out of 100 times prefer Baldwin' over Gibson, but wants to see Mel Gibson in Scorsese movie▶ 1:20:57

Joey Pants Award

Chris RyanBoggsDiscussed JC McKenzie (Damon's realtor) as a deep cut pick but agreed with Boggs as winner▶ 1:22:52
Sean FennesseyAgreed with the choice and praised the realtor character, no clear personal pick stated▶ 1:23:06

Probably Unanswerable Questions

Bill SimmonsMultiple questions: Why does Costello's lawyer give the tapes to Costigan, why Costigan has two different birth dates in his computer record, and the apartment doesn't exist issue▶ 1:46:28
Sean FennesseyWhat happens if Costigan doesn't see the envelope and Sullivan comes back saying everything checks out - does everyone just go back to their normal lives?▶ 1:45:55

Sequel/Prequel/Limited Series/Remake

Bill SimmonsA 10 episode Dignam show with Mark Wahlberg - responds 'Definitely. Sure.' when asked if it could work▶ 1:47:50
Chris RyanLimited series, not multi-season, but would need to be paced more like True Detective rather than the exhausting pace of the original movie▶ 1:47:24
Sean FennesseyAgrees it needs to be like a 'Light the Wick movie' that builds to an explosion for satisfaction, implying the original's pacing wouldn't work for a series▶ 1:47:43

Best Quote

Chris RyanTwo quotes: 'I thought I was supposed to go into shock. I'm not in shock.' and 'I fucking know you. I know your family. You make one more drug deal. I'll forget your grandmother was so nice to me and I'll cut your fucking nuts off.'▶ 1:51:03

Who Won the Movie

Bill SimmonsLeonardo DiCaprioLeonardo DiCaprio - he convinced the host that he could do anything as an actor and needed this movie for his career trajectory▶ 1:51:59
Chris RyanAcknowledges both did great but leans toward it being a tie, notes there are many winners in The Departed▶ 1:55:01
Sean FennesseyMartin ScorseseMartin Scorsese - won Best Director and Best Picture at Academy Awards, made $300 million, got two biggest movie stars to work together, achieved what he'd wanted for 30 years▶ 1:52:03

Movies Referenced (61)

Title (year)LinksMentionsMentioned byFirst
Blood Diamond (2006)IMDb ↗Lb ↗8Bill Simmons, Sean Fennessey, Chris Ryan▶ 22:29
Goodfellas (1990)IMDb ↗Lb ↗8Bill Simmons, Sean Fennessey, Chris Ryan▶ 13:34
Infernal Affairs (2002)IMDb ↗Lb ↗6Sean Fennessey, Bill Simmons, Chris Ryan▶ 29:45
Titanic (1997)IMDb ↗Lb ↗6Bill Simmons, Chris Ryan, Sean Fennessey▶ 5:40
Babel (2006)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 15:47
Children of Men (2006)IMDb ↗Lb ↗4Sean Fennessey, Bill Simmons▶ 18:42
Gangs of New York (2002)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 15:05
Raging Bull (1980)IMDb ↗Lb ↗4Chris Ryan, Bill Simmons, Sean Fennessey▶ 3:45
The Good Shepherd (2006)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 1:17:27
Batman (1989)IMDb ↗Lb ↗3Bill Simmons, Sean Fennessey, Chris Ryan▶ 55:51
Boogie Nights (1997)IMDb ↗Lb ↗3Bill Simmons▶ 5:44
Good Will Hunting (1997)IMDb ↗Lb ↗3Bill Simmons▶ 5:41

Directors Referenced (9)

NameLinksMentionsMentioned byKnown ForFirst
Michael MannIMDb ↗Lb ↗9Bill Simmons, Chris Ryan, Sean FennesseyThe Insider, Collateral, The Last of the Mohicans▶ 1:55:22
Martin ScorseseIMDb ↗Lb ↗8Sean Fennessey, Bill SimmonsTaxi Driver, Killers of the Flower Moon, Mean Streets▶ 2:33
Mel GibsonIMDb ↗Lb ↗5Bill Simmons, Sean FennesseyBraveheart, Lethal Weapon 3, Conspiracy Theory▶ 1:17:09
Sean PennIMDb ↗Lb ↗2Chris RyanMystic River, 21 Grams, Dead Man Walking▶ 1:25:50
Howard HughesIMDb ↗Lb ↗1Bill Simmons▶ 25:39
Oliver StoneIMDb ↗Lb ↗1Sean FennesseyBorn on the Fourth of July, Platoon, JFK▶ 1:33:10
Paul GreengrassIMDb ↗Lb ↗1Bill SimmonsUnited 93, News of the World▶ 17:29
Stephen FrearsIMDb ↗Lb ↗1Bill SimmonsDangerous Liaisons▶ 17:28
Tom BradyIMDb ↗Lb ↗1Bill SimmonsThe Hot Chick▶ 1:03:12

Actors Referenced (61)

NameLinksMentionsMentioned byKnown ForFirst
Matt DamonIMDb ↗Lb ↗72Bill Simmons, Chris Ryan, Sean FennesseyGood Will Hunting, The Martian, The Departed▶ 4:38
Jack NicholsonIMDb ↗Lb ↗56Bill Simmons, Chris Ryan, Sean FennesseyChinatown, As Good as It Gets, The Departed▶ 5:21
Mark WahlbergIMDb ↗Lb ↗39Bill Simmons, Chris Ryan, Sean FennesseyThe Fighter, Boogie Nights, The Departed▶ 5:21
Al PacinoIMDb ↗Lb ↗24Bill Simmons, Chris Ryan, Sean FennesseyDog Day Afternoon, The Godfather▶ 20:28
Billy CrudupIMDb ↗Lb ↗18Chris Ryan, Bill Simmons, Sean FennesseyAlmost Famous, Watchmen, The Good Shepherd▶ 11:30
Martin SheenIMDb ↗Lb ↗13Bill Simmons, Chris Ryan, Sean FennesseyThe Departed▶ 47:50
Ray WinstoneIMDb ↗Lb ↗13Bill Simmons, Sean Fennessey, Chris RyanThe Departed▶ 40:41
Vera FarmigaIMDb ↗Lb ↗12Bill Simmons, Chris RyanUp in the Air, The Departed, Orphan▶ 7:18
Robert De NiroIMDb ↗Lb ↗11Bill Simmons, Sean Fennessey, Chris RyanCape Fear, Raging Bull, Taxi Driver▶ 3:45
Arthur DignamIMDb ↗Lb ↗10Bill Simmons, Chris Ryan, Sean Fennessey▶ 36:59
Gene HackmanIMDb ↗Lb ↗10Bill Simmons, Sean FennesseyThe French Connection, The Royal Tenenbaums, Unforgiven▶ 1:28:13
Leonardo DiCaprioIMDb ↗Lb ↗10Chris Ryan, Bill Simmons, Sean FennesseyInception, The Wolf of Wall Street, The Departed▶ 11:13

Writers Referenced (5)

NameLinksMentionsMentioned byKnown ForFirst
Aaron SorkinIMDb ↗Lb ↗1Sean FennesseyA Few Good Men▶ 1:55:46
Andrew CosbyIMDb ↗Lb ↗1Bill Simmons▶ 1:40:27
Eric RothIMDb ↗Lb ↗1Sean FennesseyForrest Gump, The Curious Case of Benjamin Button▶ 1:18:14
Roger EbertIMDb ↗Lb ↗1Bill Simmons▶ 35:58
William GoldmanIMDb ↗Lb ↗1Bill SimmonsButch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 22:09

Cinematographers Referenced (3)

NameLinksMentionsMentioned byKnown ForFirst
Janusz KaminskiIMDb ↗Lb ↗2Sean FennesseySchindler's List, Minority Report▶ 1:33:23
Rodrigo PrietoIMDb ↗Lb ↗2Sean FennesseyBrokeback Mountain, The Wolf of Wall Street, Killers of the Flower Moon▶ 1:33:12
Robert RichardsonIMDb ↗Lb ↗1Sean FennesseyKill Bill: Vol. 1, Inglourious Basterds, Once Upon a Time... in Hollywood▶ 1:33:06