Jack Nicholson's Character In The Departed Was Based On A Real-Life Gangster

Jack Nicholson's character in The Departed was actually based on a real-life gangster. Watch the trailer below:

Martin Scorsese's 2006 epic crime-thriller picked up four Oscars at the 79th Academy Awards and for those unaware of the film, the official synopsis reads: "An undercover agent (Matt Damon) and a spy (Leonardo DiCaprio) constantly try to counter-attack each other in order to save themselves from being exposed in front of the authorities.

"Meanwhile, both try to infiltrate an Irish gang."

So, if that plot isn't exciting enough for you, the film features one of the most star-studded cast you'll ever see.

Leonardo DiCaprio plays Trooper William 'Billy' Costigan Jr., while Matt Damon stars as Staff Sergeant Colin Sullivan, Mark Wahlberg plays Staff Sergeant Sean Dignam, Martin Sheen is Captain Oliver 'Charlie' Queenan. And let's not forget Alec Baldwin who plays Captain George Ellerby, while Robert Wahlberg is FBI Special Agent Frank Lazio.

Last, but not least, Jack Nicholson stars as Frank Costello.

Paramount Pictures

Now, the film itself isn't based on a true story, however Nicholson's character is based on real-life Boston gangster James 'Whitey' Bulger, who led the infamous Winter Hill Gang out of Somerville, Massachusetts, in the late 20th century, as per The Wrap.

Remarkably, similar to the Costello character, Bulger was a real-life FBI informant and worked with corrupt FBI agents who helped cover up his crimes, according to The American Conservative.

Alamy

However, that's where the similarities end, as (Spoiler Alert) Nicholson's character is killed halfway through the film, while Bulger ended up fleeing Boston in 1994 and was finally arrested in Santa Monica, California, in June 2011, as per The LA Times.

He was then murdered in prison in 2018.

Scorsese was keen to base the character on Bulger so he could add 'something a little more' to the role. However, it was screenwriter William Monahan's initial idea to base the character on the Boston gangster.

"Once we began to read the books on these people and the situation in Boston at that time, nothing that we did in the film was, in a sense, exaggerated in any way," Scorsese said.

Paramount Pictures

Let's not forget Matt Damon's character, Colin Sullivan, who meets Frank Costello as a minor and is groomed to work as a mole for Costello within the Massachusetts State Police.

The character isn't too far off from real-life FBI agent John Connolly, who actually grew up in the same South Boston housing project as James 'Whitey' Bulger. 

Alamy

According to The Boston Globe, Connolly and Bulger made a deal in 1975, and for the next two decades, Bulger fed information to the bureau about the Winter Hill gang's rivals in the criminal underworld in exchange for Connolly's help preventing the FBI from prosecuting Bulger and his associates.