August 17, 2017
'The Departed'
HBO and The Ringer's Bill Simmons is joined by Chris Ryan to revisit and examine the Oscar-winning 'The Departed,' directed by Martin Scorsese and starring Matt Damon and Leonardo DiCaprio. They break down everything from who was in the original intended cast to the film's most memorable moments, as well as what the movie is trying to say about society through DiCaprio's and Damon's characters. And, of course, they unpack Jack Nicholson's memorable Boston accent.
Cast
Leonardo DiCaprio as Billy Costigan
Matt Damon as Colin Sullivan
Jack Nicholson as Frank Costello
Mark Wahlberg as Sgt. Dignam
Alec Baldwin as Cpt. Ellerby
Martin Sheen as Cpt. Queenan
Ray Winstone as Mr. French
Vera Farmiga as Dr. Madolyn Madden
Anthony Anderson as Brown
James Badge Dale as Trooper Barrigan
Mark Rolston as Fitzy
Kevin Corrigan as Costigan's cousin
Directed by: Martin Scorsese
Written by: William Monahan
Cinematography by: Michael Ballhaus
Notes
- Not a good movie year (2006) – other Best Picture nominees were Babel, The Queen, Little Miss Sunshine, and Letters from Iwo Jima. 'It feels a little makeupy but it really wasn't.'
- The F word and its derivatives are used 238 times in the movie.
- Nicholson refused to wear a Red Sox hat during filming and banned all Celtics hats on set.
- Leo got nominated for 'Blood Diamond' instead of 'The Departed' because the same studio did both – they wanted to put Leo in Best Supporting but he didn't want to campaign against everyone else in the movie.
- Wahlberg was the only cast member nominated for an acting Oscar (Best Supporting Actor).
- Chris Ryan's theory: the DiCaprio and Damon characters are a metaphor for the two ways you can live in America – compartmentalize and be blindly ambitious, or feel everything and make yourself vulnerable. Either way, America destroys you. Guys like Dignam survive.
- The movie is 'a great bad movie' – not bad like Snakes on a Plane, but bad in the sense that it doesn't make any sense. The dialogue, performances, and music make it a blast to watch. 'Perfect movies aren't always rewatchable.'
- It's a remake of the Hong Kong film Infernal Affairs, which is 'tighter than this, for sure.'
- Comparison to Heat: 'Heat was crafted, every decision well thought out. Departed feels like they're flying by the seat of their pants half the time.' But that contributes to its rewatchability.
- Nicholson had some crazy scene with prostitutes and a dildo he wanted to shoot – they talked him out of it but he kept the dildo as a prop and ad-libbed it into a scene.
Categories
Most re-watchable scene
- The first meeting with Dignam and Costigan – Chris orients his rewatch around how far back he has to rewind to get to that scene.
- 'Are you still a cop?' – the Nicholson-DiCaprio showdown. Something to be said for two giant stars in a scene together.
- Martin Sheen's death off the roof – 'the body coming off the roof, landing right in front of Leo.'
- The cranberry juice scene – 'a perfect movie scene. Everything from the music to the wide shot to Winstone's delivery.'
- Leo getting killed in the elevator – 'one of the only times I can ever remember the theater gasping like a sporting event. It's the Red Wedding of this movie.'
- Wahlberg killing Damon at the end – the outfit, the slippers, the DNA-proof getup.
What aged the best?
- Leo versus Matt Damon – the rivalry driving the whole movie.
- The title sequence coming in 18 minutes with Dropkick Murphys and Leo doing jail workouts – has to be a record for latest title card.
- Baldwin and Wahlberg running a department together – 'really could have been any department. I would have joined it.' Their department is where 'the cops watch the cops watch the cops.'
- The cranberry juice scene – 'What is it, a natural diuretic? My girlfriend drinks it when she's got her period. What, do you got your period?'
- The Nicholson death scene.
What aged the worst?
- Nicholson's entire performance – didn't even get nominated for an Oscar for a role that should have been a guaranteed Best Supporting nom. 'I don't know what accent he was going for.'
- Damon sending a whole complicated text in his pocket with T9 – 'the triple crown of texting. You could not do that on an iPhone.'
- Leo immediately panicking after seeing the Citizen Bank envelope – 'for the 1400 SATs, not great, Leo.' Leaves the envelope in a different spot; Damon spots it immediately.
- Leo's plan to trap Damon on the roof – 'these are all going to not age well because none of them make sense.' Why does he have to go to a roof with one elevator and no outs?
- Scorsese using Gimme Shelter for a third time – 'Goodfellas: home run. 'Casino': OK, maybe. 'The Departed': like Cheap Trick playing Surrender three times in a concert.'
- Mark Wahlberg's hair – 'the last relic of Mark Wahlberg hair before his hair really fell off the mountaintop.'
Casting what-ifs
- Brad Pitt was supposed to play Damon's part – dropped out, ended up producing the movie instead.
- Al Pacino was the first choice for Frank Costello – 'totally different movie.' Nicholson was second choice.
- Ray Liotta was supposed to be Dignam – couldn't do it. Dennis Leary was second choice, also couldn't do it. Wahlberg had to film all his scenes in 4 days at the start.
- De Niro turned down Martin Sheen's part because he wanted to be in The Good Shepherd.
- Mel Gibson was the first choice for Alec Baldwin's part – was filming Apocalypto.
- The RZA was offered Anthony Anderson's role – couldn't do it.
- Alternate Departed universe: Leo, Pitt, Pacino, De Niro, Mel Gibson, Ray Liotta, and the RZA. 'I think I like that movie better.'
Best "that guy"
- Mark Rolston (Boggs from Shawshank) – 'How is there a better that guy than Boggs from Shawshank?' Has a key role as the guy who turns when they arrest Fitzy.
- Kevin Corrigan as Costigan's cousin – 'the perfect cousin.' Possibly from 'Dazed and Confused', been in tons of stuff. 'Anytime you can describe someone as an idiot fucking cop magnet of a cousin, they're going to win that guy.'
- Ray Winstone as Mr. French – English guy who pulled off Boston. Turned down the role of Jimmy McNulty on The Wire.
- James Badge Dale as Trooper Barrigan – 'I've never really remember seeing this guy again.' He was in Rubicon and 13 Hours.
- Anthony Anderson – 'that guy in 2006.' He was a that guy before he became Anthony Anderson.
- David O'Hara as Fitzy – 'such a that guy that you wouldn't even know his name.'
Picking nits
- Why would Leo agree to this undercover deal? – 'You're too smart to be a cop, so instead we're going to erase your identity and send you to jail.' Great career choice.
- The apartment with the perfect State House view – 'no apartment I had ever heard of had such a great view of the State House. They made it up.'
- Leo's plan to trap Damon on the roof – has all the goods, tapes from the lawyers, but decides to meet on a random roof with an elevator and no outs instead of just handcuffing him on the street.
- Martin Sheen not suspecting Matt Damon – runs internal affairs but doesn't notice the guy who's constantly on the phone, switching things off, turning cameras off. 'Trace that call!'
- Why didn't Vera Farmiga turn Damon in? – she knows he's a liar and a bad cop. Leo's dead. Just turn him in.
- Why didn't a more famous actor play Leo's killer? – 'In the moment, I was like, I didn't know who that guy is. Where'd that guy come from?' Should have been a Ryan Gosling-level actor.
- The rat on the balcony at the end – 'if I was his assistant director, I'd be like, Martin, if you put that rat on there, I'm quitting.'
Who won the movie?
- Leonardo DiCaprio – 'After a while I just think it's Leo's movie.' First viewings you're blown away by Wahlberg, but Leo took this most seriously. 'One of his three best performances' along with Wolf and Django.
- Matt Damon credit for playing the creep well – 'Damon's best performances are always the ones where he plays the creeps, like Ripley.' But ultimately it's Leo's movie.
- Nicholson loses the movie – should have been the Jessup/Hannibal Lecter home-run part. Didn't even get an Oscar nomination. 'One of the most embarrassing moments of his career.'