Martin Scorsese joked in his Oscar acceptance speech for Best Director that The Departed was his first movie with a plot. The director’s previous classics, like Taxi Driver and Goodfellas, had effectively been sprawling character studies more concerned with the people than the events surrounding them, but in helming an English-language remake of the Hong Kong crime thriller Infernal Affairs, Scorsese had to juggle a real plot.
While Matt Damon, Leonardo DiCaprio, and Jack Nicholson ended up being the perfect stars for this movie, they weren’t the first ones considered. There are unsubstantiated rumors that Al Pacino was considered to play Frank Costello, RZA turned down the role of Trooper Brown, and Mel Gibson rejected an offer to play Ellerby because he was preparing to direct Apocalypto.
Brad Pitt As Colin Or Billy
Brad Pitt produced The Departed through his Plan B production company. Although he doesn’t appear in the final film, he was originally planning to play one of the lead roles himself. It’s unclear if Pitt wanted to play mob informant Colin Sullivan or undercover cop Billy Costigan, or if he was waiting to see the completed script before choosing which role to take on.
However, during the development of the story, Pitt decided that he was too old to play one of the lead roles and bowed out of the race. During the time when Pitt would’ve shot The Departed, he starred in Babel instead. Pitt ended up teaming up with Leonardo DiCaprio to play his character’s stunt double Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood.
Ray Liotta As Dignan
While Martin Sheen’s Captain Queenan can break difficult news lightly, his right-hand man Dignan, a sergeant played by Mark Wahlberg, is refreshingly blunt with the officers who find themselves in the captain’s office. Although Wahlberg ended up being the perfect actor to bring a vengeful edge to Dignan and a dry hilarity to his insults, he wasn’t the first person to be offered the role.
Scorsese’s original choice for the role was Ray Liotta, with whom he’d previously worked on Goodfellas. However, the actor ended up having to turn down the part due to scheduling conflicts. Liotta proved to be perfect for the role of Henry Hill, but it’s hard to imagine him nailing the role of Dignan in The Departed quite as well as Wahlberg, so maybe this was for the best.
Robert De Niro As Captain Queenan
In a movie filled with nefarious criminals and cold-blooded killers, Martin Sheen’s Captain Queenan gives viewers a glimmer of hope in humanity. He’s a sweet, sensitive guy who’s always looking out for his cops and ultimately makes a very difficult sacrifice to protect Billy’s identity. This gets him thrown off the roof of a building, after which his corpse lands conveniently at Billy’s feet. Sheen’s portrayal of this character was completely sympathetic, which gave his death scene maximum emotional impact. Sheen wasn’t the first choice for the role, though.
Originally, Scorsese approached Robert De Niro with the role of Queenan. This would’ve marked the iconic duo’s first collaboration since 1995’s Casino, more than a decade later. However, since De Niro was prepping his next directorial effort The Good Shepherd at the time, he had to turn down the role. Scorsese fans had to wait another decade before the director would reunite with De Niro on the 2019 crime epic The Irishman.
After the success of The Departed, there were rumors of a sequel revolving around Mark Wahlberg’s vigilante Dignan character and De Niro as a corrupt politician, but even if this project was once in the cards (which seems unlikely), it never came to fruition.
Denis Leary As Dignan
After Ray Liotta turned down the role of Dignan and before Mark Wahlberg was cast, the part was offered to Denis Leary, but like Liotta, he had to turn it down due to scheduling conflicts. While Leary may seem like an odd choice for such a dark role, Scorsese had apparently been impressed with Leary’s dramatic work on the show Rescue Me, which ended up running for another five seasons after The Departed hit theaters.
Although Leary had already proven himself as an actor, he’s primarily known as a standup comic. Scorsese has a history of casting comedians in his movies, having cast Ray Romano in dramatic roles in a few projects in addition to bringing in comics like Henny Youngman to cameo as themselves in various gangster epics.
Tom Cruise As Colin Or Billy
When Brad Pitt was planning to play one of the lead roles in The Departed, Tom Cruise was being eyed by the studio for the other. This wasn’t the first time that Cruise was up for the lead role in a Scorsese movie, as he’d previously been Warner Bros.’ top choice to play Ray Liotta’s role of Henry Hill in Goodfellas.
Cruise previously worked with Scorsese on The Color of Money, the director’s belated 1986 sequel to The Hustler, in which he played the young protégé of Paul Newman’s now-aging pool hustler character “Fast Eddie” Felson.
