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Episode #856: The Departed (2006, W❤️M) (Patreon)

Published:
2026-04-02 08:00:04
Imported:
2026-04
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“Martin Sheen pops like a grape!” - Andrew on Captain Queenan’s demise

On this month’s We ❤️ Movies, Remake-ril is in full effect as we chat about Martin Scorsese’s Oscar-winning remake, The Departed!

A reimagining of Andrew Lau Wai-Keung & Alan Mak’s Infernal Affairs, this is the flick that finally won Scorsese his first (and only) Oscar for directing. How majestic are all these wild-ass accents flying around this movie? Is this Marty’s most grim look at the mob? How great is this Damon/Farmiga elevator meet cute? Isn’t it great looking back at all this quaint cell phone technology? And how lucky are we to have gotten one last amazing Nicholson psycho performance? PLUS: If Yondu from Guardians of the Galaxy shows up at your apartment wearing paper booties, look out!

The Departed stars Leonardo DiCaprio, Matt Damon, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Anthony Anderson, Alec Baldwin, Kevin Corrigan, James Badge Dale, and Jack Nicholson as Frank Costello; directed by Martin Scorsese.

We hope you are enjoying We ❤️ Movies! Thanks so much for being the kick-ass Patreon supporter that you are. You help keep the lights on around the old clubhouse and us on the air. We know you have a lot of options for podcast enjoyment and we're stoked you chose to spend some time with us!

Original cover art by Felipe Sobreiro.

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Comments

LoganTheWise

Oh shit boys we're shipping up to Boston . Between this episode and the upcoming Marty series on Blank Check the hype is so real

Tim O'

How's ya mutha? Good, she's tired from fuckin' my fatha.

Jacob Ferguson

Speaking of Ray Winstone, has anyone seen Ladies and Gentlemen, the Fabulous Stains?

MarkNM

You got me back on Patreon with this one. "Fuck it."

Craig

I saw Infernal Affairs first, so that might be a factor in why I prefer it. The pacing differences can be summed up by Martin Sheen’s death - a long, slow motion shot of him falling. In the Hong Kong version the body just slams down behind Tony Leung without warning - much more shocking and effective (especially when you don’t know it’s coming!)

Tim O'

I wonder if Marty saw Fargo and thought, "Hm, a fantastic crime drama, with a relentless undercurrent of silly accents. This opens up exciting new cinematic possibilities."

James Richie

Nah, “Tessie” was the Dropkicks go to at the ballpark before Departed came out. And I always thought the suggestion was that there was a good chance DiCaprio was actually Nicholson’s biological kid.

Barista Bran

I had the Godzilla '98 soundtrack on CD and the Godzilla roars on the Green Day track FUCKING RIPPED! Too bad they didn't transition it into Jaded with some Godzilla stomps and roars

Zack Hansen

The blue screen of death.

Watch_N_Rewatch

"I'm the guy who does his job, you must be the other guy!" Love hearing the WLM boys quote their favorite lines and reminiscing the most memorable shots of the Departed, terrific movie and excellent episode boys, cheers 🍻

Matt

How mad was Wahlberg he wasn't in the scene where they beat up that shopkeeper?

Chris

He watched it from the cuck chair

RJ Cunningham

Leo sounds like he might have the same father as Will Salas

Smaug

The big knock I have against this movie is that the writing and character development for Vera Farmiga is such silly, juvenile male wish-fulfillment. "Omg Leo, your troubled past and trauma and emotional unavailability is such a turn-on, let me jeopardize my career as a professional physician and psychiatrist by fucking my patient." It's typical of the writing of the 90s and 00s that I've always felt was "I, as a Hollywood writer, have no idea what mental health professionals do and I'm vaguely disdainful of the field." So dumb.

James C Harris

I was half expecting a Flintstones/Pulp Fiction xover

I.C. Weiner

Two things not really related to the episode 1. I am a Clippers fan and fairly often go to their games. Anthony Anderson is also a Clippers fan. One night after a game he is standing outside of Staples and there is a kid selling candy bars. Anthony Anderson is lightly ribbing the kid and then buys all the boxes of chocolate the kid had. I thought it was a very sweet moment from a celebrity. 2. Bill Simmons is basically is Leo. He pretends to be an everyman from Boston but his step-dad was super rich who paid his way through everything, and his dad, the lower income parent, was the superintendent of Boston and has had Celtics season tickets for like 50 years. Everytime someone mentions him I always think of that scene from the beginning of this movie

Arthur Cunningham

There’s a You Tube vid of Damon talking about Nicholson vamping on the “she fell funny” scene that is absolutely hysterical

RJ Cunningham

Using T9 on a phone with physical buttons….I think I could pull off the long pocket text. Wish I could get buttons and T9 back on my phone

RJ Cunningham

As famous as it is this might be Nicholson’s most underrated performance

Jason

The best fun fact about Simmons is that he has spent maybe 15 months in Boston. The type of guy who would says he knows where he’s going cause he “lived here” but immediately gets lost. As a New Yorker, we got tons of those guys.

Jason

Hopefully they cover “Me Farted” the Larry the Cable Guy version. It takes place in Nashville where Larry goes undercover as a former sanitation worker with a flatulence problem. He wants to uncover the scheme of the black market Gas-X trade. Toby Keith plays Frankie Poostello and the post 9/11 commentary is way more prominent.

I.C. Weiner

Yea, dude also moved to LA as soon as possible (which, as far as I can tell from all the Bostonians who live here, they all do) and had his parents pay for his apartment so he could be a bartender and write at the same time to pull himself up by his own bootstraps.

I.C. Weiner

That is really interesting. Also, Damon has a pretty good Nicholson impression

Paul

“Just when you thought you was out, they pull you back in.”

Robert

“Wait, I'm confused about the movie. So the cops knew that Internal Affairs was setting them up?”

jribs

MVP Baseball 04-05 flashbacks

Kennieth Miles

Me in the car yelling over and over when hearing you all asking, has he made an action movie?! Gangs of New York! GANGS OF NEW YORK! GANGS OF NEW YORKKK!

Tim Batson

For anyone who is skeptical about Heat 2, I cannot recommend it enough. It's absolutely riveting and does the characters justice!

Ronnie Gardocki

I just watched that the other day. Fun City put out a 4K.

Felipe Sobreiro

Can confirm that Winstone's AH, FAHCK IT suicide impression is a long time WHM reference

RJ Cunningham

Would love to hear Cabin's thoughts on Scorsese's Cape Feare. The Departed is less frenetic, which is crazy since The Departed is fast-paced as hell. The runtime and pacing complaints are valid but 2:30 hours in 2006 is like 4:00 hours in 2026. I need to revisit Cape Feare but I do remember finding the editing was overshadowing De Niro's performance. De Niro in Cape Fear might be his greatest performance ever but it's tough to tell. The Departed is a masterpiece and still might not be a top 10 Scorsese but I feel its fame and relevance make people detract from it. Almost like some assume Scorsese overrode his directorial sense for a popcorn movie but that's not the case at all. This movie is overflowing with iconography while containing a Murderer's Row of actors, all knowing exactly how to play it. Easily Monahan's greatest script, so many lines that hit quite hard. The movie spiritually takes place in the late 80s/90s which is why the tech in the movie being so clunky almost make sense, feels like a necessity to set the movie in "current times." One final note is Southie's romanization is pretty media driven, since Good WIll Hunting. People of Boston, even the street trash of other neighborhoods, saw Southie as a no-go zone since it was a psychotic/sociopathic culture there. This explains the incestuous relationship amongst many from Southie as it was extremely insulated (The Bussing Riots centered around Southie) which led to kids from the projects ALL knowing each other. You can see this with Martin Sheen and Nicholson having a history, but also is the reason why Whitey Bulger was protected by the FBI. It was a scumbag Southie Projects kid (Connolly) that joined the FBI, but had that Southie connection which took precedent.

Jonnie Sea

I’m only like 20 minutes into this episode but Watched the movie for the second time last night (hadn’t seen it since it came out) But is Damon’s character closeted? He’s really really really comfortable dropping those F bombs (which normally would be reserved for a “dumb” character, and not taking ya know working for organized crime while being a cop into the equation, he’s not “dumb”) Plus his relationship with Vera seems very much like a shield. He’s not able to perform sexually (and we have no knowledge of a medical condition) Plus since we don’t have the politics of HK/UK/China to play off of like IA does, i thought this could be an interesting additional layer of “duplicity” Overall great movie and I’m usually not a fan of “mob movies”

Gryphon

After doing some investigating Jeff Wahlberg played Diego in that live action Dora the Explorer movie with Isabella Merced

RJ Cunningham

I was having similar thoughts, and going with the theme of pretending to be the opposite of what you are, would lend to Damon being a gay man in a straight relationship. What really makes me think Scorsese was saying that was Baldwin specifically telling Damon that married men don’t get questioned for being gay. There is also the realtor 100% being under the impression and acknowledging the fact he thinks Damon has a “house guest.” His character is definitely gay. Also feel Scorsese was touching on the Catholic Church scandal with the all these men who were boys who (as a collective) were abused by older men, thus the obsession with heterosexuality and the discussion of young boys being sexualized with a bevy of comments regarding the topic, all delivered as insults from me insecure about it

Billie Jackson

Ray Winstone's strangler that pretty much retracted on its own? He went to the Dario Argento's Trauma prop sale?

Billie Jackson

After the Winstone Pol Pot talk I was just imagining a Nil By Mouth/The Killing Fields crossover.

Aaron Dowler

“He was a cahpet layah for Jordan Mahsh” when Leo says what his uncle did for a living is my favorite bit of Boston dialogue from this movie, it feels more Boston than anything to me

Alethia St. Joan

Scorsese is currently shooting What Happens at Night, with DiCaprio and J Law.

James Richie

Yeah, there’s a lot of suggestions of Damon’s character maybe being closeted. There’s a lot that’s understated or just suggested which is weird for a film this, I dunno the right word, loud with macho deflection. The whole film seems to work like that, saying something by saying nothing. Why did Costello send a wreath to Billy’s mom’s funeral and why was Billy so seemingly pissed about it? Things like that. And there’s also a lot of Boston specifically that’s in there like the church scandal and also the whole cops are crooks, crooks are cops. The scene with Costello and Queenan where they’re talking fathers raised the question of how far these guys go back. A lot of the FBI that was supposed to be taking down Whitey and were kind of doing his job for him grew up with him in the same neighborhood with him. Everyone knew each other. The movie

Tim Cooney

Not ten minutes in and I do find the story of going to the bar they filmed at really interesting, considering how Worcester, MA has been doubling for New York in movies and for the Walking Dead (whichever one is still going on for whatever reason). Anyways, as the local vernacular goes, I’ve been wicked psyched for this ep.

Darcy MacDonald

A cut of this movie where Nicholson said "funny lookin'" at least 7 times exists

RJ Cunningham

Baldwin is so so fucking funny in this movie

Jonathan Lyons

Haven't listened yet, but I have a petition to digitally remove cabin because he is the contrarian of the podcast and it's too on the nose to have involved in We HATE Movies

profondo robbo

True, but then the trade-off is that Leung getting shot in the elevator is done in slow-motion, which (even as someone who prefers IA) I have to concede is not as effective as DiCaprio getting shot instantly.

profondo robbo

I have to assume this was at least partially inspired by having to sit through Boondock Saints and feeling the need to watch a much better Boston crime movie. I know I was rewatching those guys killing Russians and Italians and wondering how they would feel about going up against the Irish mob.

Sehnsucht666

Got me needing to watch this again ASAP. Also maybe I'm listening to the podcast too much, it's starting to suggest the guys for people I may know on Facebook

Frank Grimes

Love this movie. I think I’d put it in my top five. It’s endlessly re watchable in my opinion. This beautiful Greek tragedy where no one can pronounce the letter R.

Matt Watterson

I know part of it was being on an uncomfortable call with Nicholson’s character, but that was a particularly unenthusiastic “yes I do 😐” he gave when asked whether he wanted to keep seeing her.

Jigsaw9856

Love this film, it was my introduction to Scorsese. If you haven't seen the Simpsons parody the Debarted, I recommend checking it out, it's a pretty solid episode.