The Rewatchables: ‘The Departed’ With Bill Simmons and Chris Ryan

Published 2017-08-17; 1:00:41 by the feed.

As extracted (engineer-sonnet-2026-10-13)

The extraction calls the show “The Rewatchables (The Ringer)” and the episode “'The Departed' With Bill Simmons and Chris Ryan”.

Hosts: Bill Simmons. Guests: Chris Ryan.

Subject films: The Departed (2006).

On the transcript: Auto-transcript with no speaker labels and many name errors; sponsor reads and a Talk Thrones promo were skipped. Transcript ends at 1:00:21 and appears complete.

Added from the extractor's memory, not said

Character names (Costello, Costigan, Sullivan/Colin, Dignam, Queenan, Ellerby, Madolyn, Delahunt, Barrigan) and the actor identification of Mark Boone Junior, David O'Hara-adjacent names, Method Man for the transcribed 'The RISA', and 'The Talented Mr. Ripley' as the film behind 'Ripley' were supplied from memory, not said.
Some transcript-mangling guesses (SeatGeek, Zach McCormick, Vincent D'Onofrio) are from memory.

Awards and segments (67)

Most rewatchable scene

pick The first meeting of Dignam and Costigan at the LRB
“I think that that is the most rewatchable scene.”
Chris Ryan · 0:09:30
pick Meeting Martin Sheen on the roof, the body falling in front of Leo
“I think the most rewatchable part of this movie is meeting Martin Sheen on the roof.”
Bill Simmons · 0:14:18
floated The Nicholson and DiCaprio showdown (Are you still a cop?)
“The Nicholson DiCaprio showdown, which is great, and there's something to be said for these movie moments where it's just these two giant stars in a scene together.”
Bill Simmons · 0:09:38
floated Martin Sheen's death off the roof, the body landing in front of Leo
“Martin Sheen's death scene off the roof.”
Bill Simmons · 0:09:59
floated Wahlberg killing Matt Damon at the end
“Wahlberg killing Matt Damon at the end.”
Bill Simmons · 0:10:09
floated The Damon and Leo phone call on the dead guy's number
“The Damon Leo phone call, you're calling it dead guy's number.”
Bill Simmons · 0:10:11
floated The roof scene where Leo gets killed in the elevator
“And then finally the roof scene.”
Bill Simmons · 0:10:16

Best casting, what if? · Who was almost cast, and who else could have played the parts.

pick Brad Pitt: Pitt dropped out of the Damon part and ended up producing the movie.
“Brad Pitt was supposed to be Damon's part dropped out, ended up producing the movie.”
Bill Simmons · 0:14:43
pick Ray Liotta as Dignam: First choice for Dignam; Dennis Leary was second and also could not do it.
“Ray Liotta was supposed to be Dignam.”
Bill Simmons · 0:14:47
pick Al Pacino as Frank Costello: Nicholson was second choice for Costello.
“Nicholson, 2nd choice for Frank Costello, who is choice number one.”
Bill Simmons · 0:15:16
pick Robert De Niro: Turned it down to be in The Good Shepherd.
“De Niro, turn down Martin Sheen's part because he wanted to be in the Good Shepherd.”
Bill Simmons · 0:15:27
pick Mel Gibson: First choice, but he was filming Apocalypto.
“Mel Gibson, couldn't do Alec Baldwin's part.”
Bill Simmons · 0:15:34
pick Al Pacino as Frank Costello: Thinks Pacino would have been the better Costello and would have owned the cast-smashing scene.
“I think Costello's better with Pacino.”
Chris Ryan · 0:16:14
pick Sean Penn as Frank Costello: Imagines Penn doing the opening monologue as unhinged.
“Like, Sean Penn doing that opening monologue would have been insane.”
Chris Ryan · 0:51:55
pick Matt Damon as Billy Costigan: Switching the parts: Damon could have played Costigan, maybe better; Leo could not have played Colin.
“I actually think there's there's a chance he could have been better than Leo was in that role because he the Boston would have felt a little more authentic.”
Chris Ryan · 0:54:14
pick Josh Hartnett: Wants a more famous younger actor as Leo's killer.
“That should have been like a Ryan Gosling.”
Chris Ryan · 0:43:13

What's aged the best · What in the movie has held up best.

pick The title sequence with the Dropkick Murphys, 18 minutes in
“The title sequence coming in 18 minutes in with Dropkick Murphy.”
Bill Simmons · 0:17:49
pick The cranberry juice scene with Ray Winstone: Praised for the music, the shot and Winstone's delivery.
“Cranberry juice is a perfect movie scene.”
Bill Simmons · 0:18:41
pick The Nicholson death scene
“Well, one last one.”
Bill Simmons · 0:18:37

What's aged the worst · What in the movie has held up worst.

nominee Jack Nicholson as Frank Costello: His entire performance.
“Nicholson's entire performance.”
Bill Simmons · 0:21:25
nominee Mark Wahlberg's hair
“Mark Wahlberg's hair.”
Bill Simmons · 0:21:32
nominee Leo panicking at the end and leaving the envelope in a different place: Out of character for a supposedly super smart guy.
“completely panics.”
Bill Simmons · 0:22:18
nominee Leo's plan to trap Damon on the roof
“Leo's plan to trap Matt Damon's character on the roof.”
Bill Simmons · 0:22:32
winner Damon texting in his pocket: Chris Ryan agrees it is his pick too.
“And then finally, um, this is my, this is the winner in my, in my mind, Damon sending a whole complicated text in his pocket.”
Bill Simmons · 0:23:01
nominee Scorsese using Gimme Shelter a third time
“Oh, and then this doesn't win, but it's a nominee.”
Bill Simmons · 0:24:13

Best performance by that guy · The best performance by a familiar face whose name you would not know.

nominee Ray Winstone as Mr. French
“Ray Winstone, you mentioned him.”
Bill Simmons · 0:25:43
nominee James Badge Dale as Trooper Kerrigan: The guy who shoots video at the end.
“Trooper Kerrigan.”
Bill Simmons · 0:26:26
nominee Anthony Anderson
“Now he's Anthony Anderson, but at the time he's of that guy.”
Bill Simmons · 0:26:54
nominee David O'Hara as Fitzy
“His really name's David O'Hara.”
Bill Simmons · 0:27:03
winner Mark Rolston: Better known as Boggs from Shawshank.
“You bet better known as Boggs from Shawshank.”
Bill Simmons · 0:27:27
winner Kevin Corrigan as Costigan's cousin: Wanted co-winners; Bill and Chris agreed to disagree.
“How is there a better that guy than Bob? Kevin Morgan.”
Chris Ryan · 0:27:30

Half-assed internet research · Production trivia the hosts dug up online.

pick Ray Winstone and Jack Nicholson did not get along
“Ray Winston said him and Jack Nicholson did not get along during the filming.”
Bill Simmons · 0:28:48
pick Nicholson refused to wear a Red Sox hat and banned Celtics hats on set
“Nicholson refused to wear a Red Sox hat during the filming and banned all Celtic Cats on the set.”
Bill Simmons · 0:29:01
pick Leo dropped out of The Good Shepherd to do The Departed
“Leo dropped out of the Good Shepherd to do the departed.”
Bill Simmons · 0:29:14
pick Leo's Boston accent coach
“Leo's Boston accent coach was named J. Gianoni.”
Bill Simmons · 0:29:32
winner The F word and its derivatives used 238 times
“I spilled it, but the F word and its derivatives use 238 times.”
Bill Simmons · 0:29:48

Boston accents · Yes, maybe or no fucking way on each actor's Boston accent.

pick Matt Damon: Yes: the best ever at it.
“Yes, Damon, the best ever at it.”
Bill Simmons · 0:30:06
pick Mark Wahlberg as Dignam: Maybe: Damon is better and Wahlberg overdoes it.
“I think that Damon is better and I think Wahlberg overdoes it.”
Chris Ryan · 0:30:24
pick Alec Baldwin: Good for the most part.
“It's for the most part good.”
Bill Simmons · 0:32:04
pick Leonardo DiCaprio as Billy Costigan: Good because Costigan is a chameleon; Bill says it is fine but fades.
“So I think it works for his character, although I know that I'm in a minority in my opinion.”
Chris Ryan · 0:32:30
pick Martin Sheen: No way group: he really botched it.
“He just really botched it.”
Bill Simmons · 0:33:11
pick Vera Farmiga: No way group: she kind of quit on it.
“She kind of quit on it.”
Bill Simmons · 0:34:06
pick Jack Nicholson as Frank Costello: No way group: no one can tell what accent he is going for.
“And then Nicholson, I don't know.”
Bill Simmons · 0:34:22

The unintentional comedy award · The funniest things in the movie that were not meant to be funny.

nominee Scorsese's Rolling Stones fetish
“Scorsese Stone's fetish we covered.”
Bill Simmons · 0:35:57
nominee Nicholson's dildo
“Nicholson's dildo.”
Bill Simmons · 0:36:25
nominee The flip phones
“The flip phones are just funny now.”
Bill Simmons · 0:36:37
nominee Damon's impotency issues
“Damon's weird impetus impotency issues.”
Bill Simmons · 0:36:42
winner Jack Nicholson running away at the end: A 30-second scene of Nicholson running, body going in all directions.
“Nicholson leaves his car and starts running, and there's this 32nd scene of Jack Nicholson running.”
Bill Simmons · 0:37:19

Picking Nits · Nitpicks about a movie they love.

pick Why Leo would agree to the undercover deal
“Why would Leo agree to this undercover deal?”
Bill Simmons · 0:38:33
pick Damon's apartment with an impossible view of the State House: A Boston guy's nit.
“it always struck me that no apartment that I had ever heard of had such a great view of the state house.”
Bill Simmons · 0:39:16
pick Would Leo and the doctor actually get together
“Would Leo and the doctor actually get together?”
Bill Simmons · 0:40:11
pick Why Vera Farmiga's character does not turn Damon's character in
“Why didn't Vera Fermiga turn Damon's character in?”
Bill Simmons · 0:41:55
pick Why a more famous actor did not play Leo's killer: His biggest flaw of the movie.
“This is my biggest flaw of this movie.”
Chris Ryan · 0:42:37
pick Nicholson not suspecting Leo, or Sheen not suspecting Damon
“Nicholson, not suspecting Leo.”
Bill Simmons · 0:44:03
pick The rat on the balcony at the end: Chris Ryan reads it as a bow on the movie.
“Why didn't anyone talk Scorsese out of the rat on the balcony at the tail end?”
Bill Simmons · 0:44:30

Greatest exchange · The best lines of dialogue.

pick The cranberry juice exchange
“It's a natural diuretic.”
Bill Simmons · 0:45:35
pick Nicholson: How's your mother? She's on her way out. We all are.
“How's your mother?”
Bill Simmons · 0:45:42
pick Wahlberg: I'm the guy who does this job. You must be the other guy.: His favorite.
“This is my favorite.”
Bill Simmons · 0:45:48
pick The Baldwin marriage monologue
“The Baldwin's whole marriage monologue that ends about ladies see the ring.”
Bill Simmons · 0:46:38
pick The world needs plenty of bartenders. 2 weeks with pay.: His favorite line.
“That's my favorite line.”
Bill Simmons · 0:47:06
pick Costigan to the therapist: why don't you just give me a bottle of scotch and a handgun
“Why don't you just give me a bottle of scotch and a handgun to blow my fucking head off.”
Chris Ryan · 0:47:15

Who won the movie · Which star came out on top: Leo, Damon, Nicholson or Wahlberg.

winner Leonardo DiCaprio as Billy Costigan: Wahlberg wows at first, but after a while it is Leo's movie.
“but after a while, I just think it's Leo's movie.”
Chris Ryan · 0:47:37
winner Leonardo DiCaprio as Billy Costigan
“I'm with you on Leo.”
Bill Simmons · 0:48:17
nominee Mark Wahlberg as Dignam: Wins the first few viewings.
“First few years, I think you're just blown away by Wahlberg.”
Chris Ryan · 0:47:31
nominee Matt Damon: Praised: his best work comes when he plays creeps.
“Matt Damon's best performances are always the one where he plays the creeps”
Chris Ryan · 0:47:42
nominee Jack Nicholson as Frank Costello: Says he loses the movie.
“And now let's have the Nicholson conversation because I think he loses the movie.”
Bill Simmons · 0:48:20

Departed 2 · A sequel or prequel they would make.

pick Departed 2, a prequel or a follow-up with Wahlberg
“I think you could argue Departed 2 could have been afterwards with like Wahlberg and you just bring people in.”
unknown · 0:55:03

Films that came up

Claims (37)

unmapped (audience anticipation): The Departed → Gangs of New York. Simmons felt the same big-names anticipation for Gangs of New York as for The Departed.
“the other time I remember feeling it was gangs, gangs of New York in 2002”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:02:01 · Chris Ryan (0.50 sure it was them)
unmapped (too satisfying): The Departed → No Country for Old Men. Seeing something that is exactly what you want, like this cast or No Country, can feel weirdly unsatisfying.
“I had it too when I saw No Country for Old Men because I love that book so much.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:02:24 · Chris Ryan (0.60 sure it was them)
career (career peak): The Departed → Boogie Nights. 1997 was a better year for Leo, Damon, Nicholson and Wahlberg than 2006: Boogie Nights, Good Will Hunting, Titanic, As Good as It Gets.
“Wahlberg had boogie nights.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:04:58 · Chris Ryan (0.50 sure it was them)
industry (same studio campaign): Leonardo DiCaprio → Blood Diamond. Leo was campaigned for Blood Diamond instead of The Departed because one studio made both.
“Leo got nominated for Blood Diamond because the same studio did Blood Diamond and the Departed.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:08:22 · Bill Simmons (0.70 sure it was them)
verdict (favorite performances): Leonardo DiCaprio → The Wolf of Wall Street. This, Wolf and Django are Ryan's three favorite Leo performances, not The Revenant.
“I would say this Wolf and Django are my 3 favorite Leo performances.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:09:01 · Chris Ryan (0.60 sure it was them)
unmapped (star clash): The Departed → Heat. The Nicholson-DiCaprio scene echoes the Pacino-De Niro anticipation of their Heat scene, though with less weight.
“it was like this anticipation of Pacino and De Niro finally being in a scene together.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:09:47 · Bill Simmons (0.65 sure it was them)
unmapped (greatest hits): The Departed → Goodfellas. Ryan says The Departed recycles Scorsese's camera moves from his career like a greatest-hits album, with no single shot to rival the Copacabana tracking shot or the Goodfellas freeze frames.
“there's not one single shot in the departed that you would put up against like the Copacabana tracking shot or any of the slow-mo freeze frame stuff and Goodfellas or Raging Bull”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:11:53 · Chris Ryan (0.75 sure it was them)
people (third collaboration): Martin Scorsese → Leonardo DiCaprio. Leo took the movie seriously partly because this was his third film with Scorsese and his chops were not yet proven.
“Martin Scorsese directed me for the 3rd time, and I'm having a good career, but I haven't really proven my chops yet.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:13:05 · Bill Simmons (0.60 sure it was them)
what-if (casting what-if): Jack Nicholson → Al Pacino. Pacino was first choice for Costello and Simmons thinks he would have been better, though over the top.
“I think Costello's better with Pacino.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:16:14 · Bill Simmons (0.70 sure it was them)
unmapped (passed the part): Brad Pitt → Matt Damon. Pitt dropped out of the Damon role and produced; Damon later passed Manchester by the Sea to Casey Affleck in a similar gesture.
“Matt Damon later paying it forward in that same way, giving Casey Affleck, Manchester.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:17:38 · Bill Simmons (0.65 sure it was them)
craft (craft): The Departed → Dropkick Murphys. The Dropkick Murphys needle drop over the title sequence is singled out as a high point of the film.
“The title sequence coming in 18 minutes in with Dropkick Murphy.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:17:49 · Bill Simmons (0.50 sure it was them)
craft (soundtrack): The Departed → Goodfellas. Asked which soundtrack he prefers, Simmons picks Goodfellas.
“Which soundtrack do you prefer this or Goodfellas?”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:21:18 · Bill Simmons (0.70 sure it was them)
unmapped (repeated song): The Departed → Casino. Scorsese used Gimme Shelter a third time here after Goodfellas and Casino, which they find funny and a sign of his Stones fetish.
“Scorsese using Gimme Shelter 3rd time.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:24:16 · Bill Simmons (0.70 sure it was them)
craft (craft): Martin Scorsese → Robbie Robertson. A host says Robbie Robertson mostly serves as music supervisor on Scorsese's soundtracks.
“Robbie Robertson from the band for these soundtracks where Robbie will do a little bit of music, but for the most part, he's the music supervisor.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:24:45 · Bill Simmons (0.50 sure it was them)
contrast (contrast): The Departed → Robbie Robertson. A host says that for the fee a name like Robertson commands, the Departed soundtrack should beat classic-radio picks like Gimme Shelter.
“you could do better than every classic radio station in America”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:24:51 · Bill Simmons (0.50 sure it was them)
unmapped (signature obsessions): Martin Scorsese → Robert De Niro. Simmons sums up Scorsese as loving De Niro, the Stones, and people getting hit over the head with a glass in a bar.
“He loved Bob De Niro, called him Bob, the stones, and people getting hit over the head in a bar with a glass.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:25:28 · Bill Simmons (0.65 sure it was them)
unmapped (turned down): Ray Winstone → The Wire. Winstone turned down the McNulty role that became The Wire's, per Simmons's Googling.
“Turned down the role of Jimmy McDulty in 2002.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:26:14 · Bill Simmons (0.65 sure it was them)
people (that guy): The Departed → The Wire. James Badge Dale shows up in lots of things, and they note Black Hawk Down had every actor.
“Every single actor was in Black Hawk Down, so you can just say.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:26:46 · Chris Ryan (0.50 sure it was them)
people (that guy): Mark Boone Junior → The Shawshank Redemption. Delahunt is played by Boggs from Shawshank, who led the sisters and became forever known for that role.
“Boggs from Shawshank has a key role in this movie.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:27:55 · Bill Simmons (0.60 sure it was them)
unmapped (dropped out for): Leonardo DiCaprio → The Good Shepherd. Leo left The Good Shepherd to do The Departed, and De Niro turned down Sheen's part to do it.
“Leo dropped out of the Good Shepherd to do the departed.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:29:14 · Bill Simmons (0.60 sure it was them)
craft (craft): Leonardo DiCaprio → J. Gianoni. Leo's Boston accent coach on the film is named as J. Gianoni.
“Leo's Boston accent coach was named J. Gianoni.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:29:32 · Chris Ryan (0.50 sure it was them)
unmapped (Boston accent): Matt Damon → Good Will Hunting. Damon is the best Boston accent in the cast, going back to Good Will Hunting.
“Goodwill hunting, the part is the best.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:30:09 · Chris Ryan (0.50 sure it was them)
industry (accent rivalry): Mark Wahlberg → Matt Damon. Damon's Boston accent is better; Wahlberg overdoes it.
“I think that Damon is better and I think Wahlberg overdoes it.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:30:24 · Chris Ryan (0.80 sure it was them)
what-if (what-if): Martin Sheen → J. Gianoni. A host suggests the production should have had the accent coach voice Martin Sheen's lines while cutting to reaction shots.
“get, you know, JG and Oni in there to do his accent”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:33:40 · Chris Ryan (0.40 sure it was them)
unmapped (real-life model): Jack Nicholson → Whitey Bulger. Nicholson is basically playing Whitey Bulger, a Boston crime lord who would not refuse a Red Sox hat.
“he basically playing Whitey Bulger.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:34:35 · Chris Ryan (0.50 sure it was them)
unmapped (Boston geography): The Departed → Blown Away. Blown Away has its own violations of Boston geography, like a downhill chase for fifteen blocks and a Four Seasons view that does not exist.
“Blown away with Jeff Bridges, which has its own just severe violations of Boston.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:39:41 · Bill Simmons (0.65 sure it was them)
lineage (homage): The Departed → Scarface. The film has references to classic gangster films like the original Scarface that feel like pastiche.
“there's a couple of references in this movie to classic gangster films like the original Scarface”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:45:24 · Chris Ryan (0.50 sure it was them)
unmapped (creep vs sweetheart): Matt Damon → The Martian. Damon's best work is the creeps like Ripley, and Ryan prefers that to his America's sweetheart phase in The Martian.
“Matt Damon's best performances are always the one where he plays the creeps, like Ripley”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:47:42 · Chris Ryan (0.75 sure it was them)
unmapped (Hannibal Lecter part): Jack Nicholson → A Few Good Men. A role like Costello, like Jessup or Lecter, is a home-run part that should get a supporting actor nod.
“This was like the Hannibal Lecter, that even the Jessup and Fugon man.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:49:34 · Bill Simmons (0.60 sure it was them)
people (same actor, different result): The Departed → A Few Good Men. Nicholson nailed every line of Sorkin's watertight script in A Few Good Men but is all over the place in The Departed.
“he nails every line of Sorkin dialogue. It's like watertight script.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:50:13 · Chris Ryan (0.60 sure it was them)
unmapped (Whitey Bulger movie): The Departed → The Irishman. Scorsese's next gangster movie with De Niro, Pacino and Pesci would be de-aged digitally and paid for by Netflix.
“It's De Niro Pacino and Joe Pesci.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:52:21 · Chris Ryan (0.50 sure it was them)
unmapped (fun villain): The Silence of the Lambs → Manhunter. Hopkins makes Lecter delightful so Silence is rewatched more than the terrifying Manhunter, an argument Simmons uses to defend a fun Costello.
“I watch Signs of the Lambs, more than Manhunter, partially because Anthony Hopkins is like almost delightful to watch, whereas Brian Cox is just terrifying in Manhunter.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:52:45 · Bill Simmons (0.50 sure it was them)
unmapped (speech): The Departed → Glengarry Glen Ross. Wahlberg dressing down Leo is called the Alec Baldwin Glengarry speech.
“he gives him the Alec Baldwin Glengarry speech.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:56:00 · Bill Simmons (0.50 sure it was them)
unmapped (flaws make it rewatchable): The Departed → Cast Away. Simmons likes movies with questions to chew on, like Cast Away, which he can talk about for an hour.
“The flaws do make it more rewatchable, right?”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:56:54 · Bill Simmons (0.75 sure it was them)
unmapped (perfect vs rewatchable): The Departed → No Country for Old Men. No Country is note perfect but he has watched it far fewer times than The Departed, because flawed movies leave room to check out and ask questions.
“I have watched it 80% less than the departed because the departed, it actually feels like a roller coaster ride when you're on it.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:57:06 · Chris Ryan (0.65 sure it was them)
craft (crafted vs improvised): The Departed → Heat. Heat is long and full of huge stars like this, but Mann's decisions were all considered while The Departed feels like flying by the seat of its pants.
“I felt like heat was crafted. Every decision he makes is really well thought out”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:58:26 · Chris Ryan (0.70 sure it was them)
lineage (remake source): The Departed → Infernal Affairs. The Departed is a remake of the Hong Kong film Infernal Affairs, which is tighter.
“It was called Infernal Affairs, the Hark Kong one?”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:59:09 · Chris Ryan (0.50 sure it was them)

Fun items (22)

fun, about The Departed: The F word and its variations appear 238 times, making it a tough fit for basic cable.
“there's 238 swears or variations of the F word in this movie”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:03:12 · Bill Simmons (0.70 sure it was them)
fun, about Martin Scorsese: Scorsese won Best Picture and Director for it as a perceived make-up Oscar in a weak year; Wahlberg was the only cast member nominated.
“It was just a really, really, really, really bad movie year.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:08:02 · Chris Ryan (0.50 sure it was them)
fun, about Leonardo DiCaprio: The scene where Leo is killed made the theater gasp like at a sporting event, the Red Wedding of this movie.
“It's the red wedding of this movie.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:10:58 · Chris Ryan (0.55 sure it was them)
fun, about The Departed: Casting what-ifs: Pitt (producer) was Damon's part, Liotta then Leary for Dignam, Pacino for Costello, De Niro for Sheen's part, Gibson for Baldwin's.
“Brad Pitt was supposed to be Damon's part dropped out, ended up producing the movie.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:14:43 · Bill Simmons (0.75 sure it was them)
fun, about The Departed: Wahlberg and Baldwin were shot first because the production only had them for about four days.
“Mark Wahlberg had to film all the scenes at the beginning of the filming because they only had them for like 4 days.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:14:54 · Bill Simmons (0.60 sure it was them)
fun, about Jack Nicholson: Nicholson reportedly wanted a prostitute scene with a dildo, was talked out of it, but kept the prop and ad-libbed it into the movie theater scene.
“he had some crazy hooker scene with dildos that he wanted to shoot and they talked him out of it”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:16:48 · Chris Ryan (0.50 sure it was them)
fun, about The Departed: The title card arrives 18 minutes in, after a long Nicholson voiceover; Leo pulling up in jail is where the title lands.
“The title sequence coming in 18 minutes in with Dropkick Murphy.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:17:49 · Bill Simmons (0.60 sure it was them)
fun, about Ray Winstone: The cranberry juice scene: Leo smashes a glass on a guy's head, then Winstone steps in and declares who you can and can't hit. Called a perfect movie scene.
“Cranberry juice is a perfect movie scene.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:18:41 · Chris Ryan (0.55 sure it was them)
fun, about Martin Scorsese: Nobody ever leaves a bar alive in a Scorsese movie; Scorsese holds the record for highball glasses to the head.
“Nobody ever gets out of a bar alive in a Scorsese movie.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:20:01 · Bill Simmons (0.60 sure it was them)
fun, about The Departed: Worst-aged plot point winner: Damon texting a long message from inside his pocket on a flip phone, the triple crown of texting.
“It's the triple crown of texting.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:23:28 · Bill Simmons (0.50 sure it was them)
fun, about Mark Boone Junior: That Guy Award: Boggs from Shawshank, who led the sisters, plays Delahunt here; Simmons backs Kevin Corrigan as Costigan's cousin.
“Boggs from Shawshank has a key role in this movie.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:27:55 · Bill Simmons (0.55 sure it was them)
fun, about Jack Nicholson: Half-assed research: Nicholson reportedly refused to wear a Red Sox hat and banned Celtics gear on the set, and he and Ray Winstone did not get along.
“Nicholson refused to wear a Red Sox hat during the filming and banned all Celtic Cats on the set.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:28:58 · Bill Simmons (0.60 sure it was them)
fun, about Mark Wahlberg: Rumor: Wahlberg built his performance from the people who arrested him in his youth and claimed the best Boston accent.
“he based his performance based on a compilation of all the different people who arrested him when he was a youth.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:31:45 · Chris Ryan (0.45 sure it was them)
fun, about Martin Sheen: Idea: keep Sheen's hangdog acting but cut to reaction shots when he talks and dub in the accent coach, as supposedly done on Ozark.
“I almost think they should have done this from Martin Sheen.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:33:37 · Bill Simmons (0.60 sure it was them)
fun, about Martin Scorsese: Scorsese used Gimme Shelter three times; they joke about a YouTube video putting it over Silence and Kundun.
“We should make a video, a YouTube video of Martin Scorsese movies that couldn't have the stones, but put give me shelter over like silence.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:36:03 · Bill Simmons (0.70 sure it was them)
fun, about Matt Damon: Damon reportedly brainstormed his character's impotence issues.
“So supposedly he brainstormed it.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:36:47 · Bill Simmons (0.40 sure it was them)
fun, about Jack Nicholson: Winner of unintentional comedy: a 32-second Nicholson run at the end with his body going in nine directions.
“there's this 32nd scene of Jack Nicholson running.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:37:19 · Bill Simmons (0.55 sure it was them)
fun, about The Departed: Ryan's overarching theory: Leo and Damon are two ways of living in America, compartmentalized ambition vs vulnerability, and America destroys both while guys like Dignam survive.
“either way, even no matter which road you choose, America will destroy you.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:40:56 · Chris Ryan (0.70 sure it was them)
fun, about The Departed: The film's biggest ridiculous plot points: Leo's roof plan, the invented Boston State House apartment view, the rat on the balcony.
“Why didn't anyone talk Scorsese out of the rat on the balcony at the tail end?”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:44:32 · Bill Simmons (0.60 sure it was them)
fun, about The Departed: Best lines: cranberry juice, 'Maybe, maybe not', 'We all are. Let's act accordingly', and 'The world needs plenty of bartenders. 2 weeks with pay.'
“And then uh, the world needs plenty of bartenders.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:47:01 · Bill Simmons (0.55 sure it was them)
fun, about The Departed: Departed 2 rumors existed; Wahlberg pitched a sequel to Scorsese over dinner.
“There are more stories to tell in this world.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:55:13 · Chris Ryan (0.45 sure it was them)
fun, about Mark Wahlberg: Rule of A-Listers: when someone gets punched, it evens out later. Damon punched Wahlberg, who got payback by shooting him at the end.
“the rule of A-Listers is that if somebody gets punched, you get to punt, there's it always ends even.”
The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:55:39 · Bill Simmons (0.40 sure it was them)

Who's talking

Bill Simmons (host): Loves big star-driven movies and sets the show's categories; adores the Wahlberg and Baldwin scenes, Boston flavor and the crazy cast what-ifs. Can't stand Nicholson's performance here, implausible plot points and the rat. A sucker for 'that guy' actors, Goodfellas and Boston details.
Chris Ryan (guest): Film-nerd who loves ambitious Scorsese and Michael Mann movies, a good screenplay and thematic readings. Pushes the capitalism theory and defends flaws as the source of rewatchability. Can't stand the Costello role being unfun, or the rat; likes Leo's performance and Vera Farmiga's therapy scenes.

The show's recurring bits

Apex Mountain: The moment a star peaks; where on the mountain a performance sits.
Who Won the Movie: The hosts name the person who came out of the film best off.
The Ebert review: Roger Ebert's original review and star rating read aloud. Ebert is cited, never on the show.
Casting what-ifs: Who was almost cast, or who should have been.
Most rewatchable scene: The scene each host would stop on while flipping channels.
Aged best / aged worst: What holds up and what does not.
Picking Nits: The little things in a film the hosts love that they don't think totally work: the nits.
Double feature: The film each host would pair it with; a programming pick.

Names the transcriber got wrong

Seek Geek / seekeek.com = SeatGeek
mold = mole
Tuna lady = Tuna / 'Tuna lady' unclear
Dingham / Dignam
Kevin Costigan = Sean Costigan (Kevin Corrigan's character)
Kevin Morgan / Kevin Corrigan
Mark Ralston / Mark Boone Junior
Boggs from Shawshank = Bogs Diamond
Viking from Bad Boys = Vincent D'Onofrio? uncertain
Lace curtains = 'lace curtain Irish'
Bugs = Bogs
Zach Mac = producer Zach McCormick
Rizza = RZA / possibly Method Man
Winston = Winstone
James Badgedale = James Badge Dale
Trooper Kerrigan = Trooper Barrigan
Sign of the Lambs = Silence of the Lambs
Fugum Man = A Few Good Men
Josh Berlin = Josh Brolin
Wahberg = Wahlberg
Dion Waiters game = refers to a basketball player
JG and Noni = J. Gianoni
Moynihan = William Monahan
Mecha trip industry = Chinese microchip subplot
Castaway = Cast Away
Peter Mullen = Peter Mullan