Hef's Movie Notes: The Departed

By Hugh Hefner

Violence, bloodshed, and mobsters; it's just another night at the mansion with Hugh Hefner.

Tonight: Leonardo DiCaprio, Matt Damon, Jack Nicholson and Mark Wahlberg in Martin Scorsese’s new American classic The Departed.

Though set in Boston, The Departed is actually an adaptation of a 2002 Hong Kong film, Infernal Affairs. Warner Bros. bought the rights for $1.75 million in 2003.

The film is about a notorious Irish mob boss Frank Costello (played by Nicholson) who plants an informant within the Massachusetts State Police. Simultaneously, the police assign an undercover cop (played by DiCaprio) to infiltrate Costello’s crew.

When both sides of the law realize the situation, each man attempts to discover the other’s true identity before being found out himself.

The Nicholson character is based on James “Whitey” Bulger, an Irish-American mobster in Boston who was secretly an FBI informant for more than three decades. The revelation that the FBI had long protected Bulger and his gang from prosecution caused a major scandal in Boston law enforcement.

Damon’s character is based on John Connolly, the FBI agent who tipped off Bulger, allowing him to evade arrest for years. Today, Connolly is in prison for his role in Bulger’s criminal activities.

DiCaprio’s undercover role as a former state trooper who joins the Irish mob parallels the story of Richard Marimick, a former state trooper who later joined Bulger’s gang.

DiCaprio had worked for Scorsese before—in The Gangs of New York (2002) and, more recently, in The Aviator as Howard Hughes in 2004.

Scorsese’s first important film, Mean Streets (1973), starred Robert De Niro; De Niro was originally scheduled to appear The Departed, but he dropped out to work on The Good Shepherd in 2006, which he also directed and produced—an unfortunate decision. De Niro’s role was then given to Martin Sheen.

Nicholson originally turned down his role in The Departed, but then Scorsese and DiCaprio ganged up on him.

He finally decided to take the part because he thought a change of pace would be good for his career after a string of comedies. Scorsese let Nicholson improvise many of his scenes because his character is supposed to be unpredictable.

In real life, Nicholson is a Lakers and Yankee fan. That’s why he refused to wear a Boston Red Sox hat and wore a Yankees hat instead.

Damon’s role originally went to Brad Pitt. But he dropped out to appear in Babel (2006). Pitt’s company (Plan B, Inc.), co-owned by then-wife Jennifer Aniston, still co-produced the film.

Wahlberg based his role on recollections of how police behaved during the approximately 25 times he was arrested. Wahlberg got the part when Denis Leary had a scheduling conflict and couldn’t accept the role. Ray Liotta was offered the part, but he, too, had other commitments.

Alec Baldwin won his role when Mel Gibson was otherwise occupied making Apocalypto (2006).

Vera Farmiga is the highest billed woman in the cast. She played George Clooney’s girlfriend in Up in the Air. Scorsese chose her over better-known stars Hilary Swank and Kate Winslet.

The Departed was shot mostly in Brooklyn and Boston. New York offered a 15-percent state tax credit so the producers frequently used New York to represent Boston.

The production ran from April 25 to September 15, 2005, on a $90 million budget.

22 people are killed on screen.

The word fuck is used 23 times.

The film premiered on September 26, 2006, to rave reviews and blockbuster box office.

Kenneth Turan declared in the L.A. Times, “The Departed is almost impossible to resist….”

Variety stated: “Mixing it up with modern mobsters for the first time since Casino 11 years ago, Martin Scorsese cooks up a juicy and bloody steak of a movie in The Departed. … Pulses with energy, tangy dialogue and crackling performances from a fine cast, combining to give Warner Bros. a winning hand commercially in all markets….”

The worldwide gross was nearly $290 million, the most successful Scorsese film in history—outgrossing The Aviator by $70 million.

The Departed won Oscars for Best Picture, Best Director (Scorsese’s first Academy Award), Best Screenplay and Best Editing. Wahlberg was nominated as Best Supporting Actor.

Many thought Scorsese’s Oscar was long overdue. In accepting the award he said, “This is the first movie I have ever made with a plot!”

So now, Martin Scorsese’s crime classic, The Departed.


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