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

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

IMDb ↗Letterboxd ↗

Categories

Apex Mountain

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

Most Rewatchable Scene

Bill Simmons▶ 36:58Wahlberg 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
Chris Ryan▶ 41:57Agreed with the Wahlberg/Leo scene and praised Leo meets Costello in the bar as one of his favorite character introductions
Sean Fennessey▶ 40:53Agreed with the cranberry juice scene and discussed the Leo/Costello bar meeting dynamics

Casting What-Ifs

Bill Simmons▶ 1:18:38Al Pacino — Presents 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
Chris Ryan▶ 1:15:55Matt Damon — Prefers 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
Sean Fennessey▶ 1:20:57Alec Baldwin — Prefers 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

Joey Pants Award

Bill Simmons▶ 1:23:03Boggs
Chris Ryan▶ 1:22:52Boggs — Discussed JC McKenzie (Damon's realtor) as a deep cut pick but agreed with Boggs as winner
Sean Fennessey▶ 1:23:06Agreed with the choice and praised the realtor character, no clear personal pick stated

Probably Unanswerable Questions

Bill Simmons▶ 1:46:28Multiple 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
Sean Fennessey▶ 1:45:55What 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?

Sequel/Prequel/Limited Series/Remake

Bill Simmons▶ 1:47:50A 10 episode Dignam show with Mark Wahlberg - responds 'Definitely. Sure.' when asked if it could work
Chris Ryan▶ 1:47:24Limited series, not multi-season, but would need to be paced more like True Detective rather than the exhausting pace of the original movie
Sean Fennessey▶ 1:47:43Agrees 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

Best Quote

Chris Ryan▶ 1:51:03Two 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.'

Who Won the Movie

Bill Simmons▶ 1:51:59Leonardo DiCaprio — Leonardo DiCaprio - he convinced the host that he could do anything as an actor and needed this movie for his career trajectory
Chris Ryan▶ 1:55:01Acknowledges both did great but leans toward it being a tie, notes there are many winners in The Departed
Sean Fennessey▶ 1:52:03Martin Scorsese — Martin 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

Movies Referenced (58)

The Town (2010)

9 mentions · Bill Simmons, Chris Ryan, Sean Fennessey▶ 3:34IMDb ↗Lb ↗

Blood Diamond (2006)

8 mentions · Bill Simmons, Sean Fennessey, Chris Ryan▶ 22:29IMDb ↗Lb ↗

Goodfellas (1990)

8 mentions · Bill Simmons, Sean Fennessey, Chris Ryan▶ 13:34IMDb ↗Lb ↗

Infernal Affairs (2002)

6 mentions · Sean Fennessey, Bill Simmons, Chris Ryan▶ 29:45IMDb ↗Lb ↗

Titanic (1997)

6 mentions · Bill Simmons, Chris Ryan, Sean Fennessey▶ 5:40IMDb ↗Lb ↗

Babel (2006)

4 mentions · Bill Simmons, Sean Fennessey▶ 15:47IMDb ↗Lb ↗

Children of Men (2006)

4 mentions · Sean Fennessey, Bill Simmons▶ 18:42IMDb ↗Lb ↗

Gangs of New York (2002)

4 mentions · Bill Simmons, Sean Fennessey▶ 15:05IMDb ↗Lb ↗

Raging Bull (1980)

4 mentions · Chris Ryan, Bill Simmons, Sean Fennessey▶ 3:45IMDb ↗Lb ↗

The Good Shepherd (2006)

4 mentions · Bill Simmons, Sean Fennessey▶ 1:17:27IMDb ↗Lb ↗

Boogie Nights (1997)

3 mentions · Bill Simmons▶ 5:44IMDb ↗Lb ↗

Good Will Hunting (1997)

3 mentions · Bill Simmons▶ 5:41IMDb ↗Lb ↗

Directors Referenced (9)

Michael Mann

9 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for The Insider, Collateral, The Last of the Mohicans▶ 1:55:22IMDb ↗Lb ↗

Martin Scorsese

8 mentions · Sean Fennessey, Bill Simmons · Known for Taxi Driver, Killers of the Flower Moon, Mean Streets▶ 2:33IMDb ↗Lb ↗

Mel Gibson

5 mentions · Bill Simmons, Sean Fennessey · Known for Braveheart, Conspiracy Theory▶ 1:17:09IMDb ↗Lb ↗

Sean Penn

2 mentions · Chris Ryan · Known for Mystic River, 21 Grams, Dead Man Walking▶ 1:25:50IMDb ↗Lb ↗

Howard Hughes

1 mentions · Bill Simmons▶ 25:39IMDb ↗Lb ↗

Oliver Stone

1 mentions · Sean Fennessey · Known for Born on the Fourth of July, Platoon, JFK▶ 1:33:10IMDb ↗Lb ↗

Paul Greengrass

1 mentions · Bill Simmons · Known for United 93, News of the World▶ 17:29IMDb ↗Lb ↗

Stephen Frears

1 mentions · Bill Simmons · Known for Dangerous Liaisons▶ 17:28IMDb ↗Lb ↗

Tom Brady

1 mentions · Bill Simmons · Known for The Hot Chick▶ 1:03:12IMDb ↗Lb ↗

Actors Referenced (61)

Matt Damon

72 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Good Will Hunting, The Martian, The Departed▶ 4:38IMDb ↗Lb ↗

Jack Nicholson

56 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Chinatown, As Good as It Gets, The Departed▶ 5:21IMDb ↗Lb ↗

Mark Wahlberg

39 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for The Fighter, Boogie Nights, The Departed▶ 5:21IMDb ↗Lb ↗

Al Pacino

24 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Dog Day Afternoon, The Godfather▶ 20:28IMDb ↗Lb ↗

Billy Crudup

18 mentions · Chris Ryan, Bill Simmons, Sean Fennessey · Known for Almost Famous, Watchmen, The Good Shepherd▶ 11:30IMDb ↗Lb ↗

Martin Sheen

13 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for The Departed▶ 47:50IMDb ↗Lb ↗

Ray Winstone

13 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Departed, Sexy Beast▶ 40:41IMDb ↗Lb ↗

Vera Farmiga

12 mentions · Bill Simmons, Chris Ryan · Known for Up in the Air, The Departed, Orphan▶ 7:18IMDb ↗Lb ↗

Robert De Niro

11 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Cape Fear, Raging Bull, Taxi Driver▶ 3:45IMDb ↗Lb ↗

Arthur Dignam

10 mentions · Bill Simmons, Chris Ryan, Sean Fennessey▶ 36:59IMDb ↗Lb ↗

Gene Hackman

10 mentions · Bill Simmons, Sean Fennessey · Known for The French Connection, The Royal Tenenbaums, Unforgiven▶ 1:28:13IMDb ↗Lb ↗

Leonardo DiCaprio

10 mentions · Chris Ryan, Bill Simmons, Sean Fennessey · Known for Inception, The Wolf of Wall Street, The Departed▶ 11:13IMDb ↗Lb ↗

Writers Referenced (5)

Aaron Sorkin

1 mentions · Sean Fennessey · Known for A Few Good Men▶ 1:55:46IMDb ↗Lb ↗

Andrew Cosby

1 mentions · Bill Simmons▶ 1:40:27IMDb ↗Lb ↗

Eric Roth

1 mentions · Sean Fennessey · Known for Forrest Gump, The Curious Case of Benjamin Button▶ 1:18:14IMDb ↗Lb ↗

Roger Ebert

1 mentions · Bill Simmons▶ 35:58IMDb ↗Lb ↗

William Goldman

1 mentions · Bill Simmons · Known for Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 22:09IMDb ↗Lb ↗

Cinematographers Referenced (3)

Janusz Kaminski

2 mentions · Sean Fennessey · Known for Schindler's List, Minority Report▶ 1:33:23IMDb ↗Lb ↗

Rodrigo Prieto

2 mentions · Sean Fennessey · Known for Brokeback Mountain, The Wolf of Wall Street, Killers of the Flower Moon▶ 1:33:12IMDb ↗Lb ↗

Robert Richardson

1 mentions · Sean Fennessey · Known for Kill Bill: Vol. 1, Inglourious Basterds, Once Upon a Time... in Hollywood▶ 1:33:06IMDb ↗Lb ↗