The real-life figure who hated being played by Jack Nicholson: “Shook his head in disgust”
Throughout Hollywood history, biopics of real-life figures have been a reliable source of acclaim and box-office success. However, Tinseltown also has a history of basing fictional characters on real-life people, even when not making a straight biopic. It’s often a way to inject a strain of reality into a film, lending it a believability that might not have existed otherwise. For example, in 2006, Jack Nicholson played a fictionalised version of a notorious criminal in a movie that won plaudits from all corners. Well, almost all corners – because the outlaw reportedly hated Nicholson’s interpretation of him.
In ’06, an off-duty California Sheriff’s deputy was catching a new movie in a San Diego cinema when he noticed something strange. You see, this deputy wasn’t originally from California. Instead, he hailed from Boston and was positive that he had spotted one of his hometown’s most infamous gangsters in the theatre. He took a closer look and became convinced that the man was indeed James ‘Whitey’ Bulger, a mob boss known for his propensity for violence – not to mention his 20-year side gig as an FBI informant who squealed on his gangster cohorts to avoid being prosecuted himself.
There were two things about the situation that struck the deputy as particularly unusual, though. For one thing, Bulger was on the lam from the FBI at that time, having disappeared in late 1994 when his corrupt FBI handler tipped him off that a RICO indictment was about to come down on his head. He was one of the most wanted men in America, yet he had jeopardised his freedom to go to the movies.
Then the deputy realised why Bulger had stuck his neck out for this particular film. It was because he wanted to see one of Hollywood’s most iconic performers play him. You see, Bulger was watching The Departed in that San Diego movie house.
Martin Scorsese’s Oscar-winning undercover cop versus undercover gangster flick featured Nicholson as Frank Costello, a terrifying Boston mob boss who ruled over the city with an iron fist. In the movie, he is quick to violence and is obsessed with rooting out a ‘rat’ in his organisation, but a late twist reveals that he is a hypocrite who has been an FBI informant. Sound familiar? It should.
In Directors Close-up 2, Scorsese revealed that he was struggling to get Nicholson to commit to playing Costello in the movie. But then screenwriter William Monahan had a brainwave: what if they based the character on Bulger? “Nobody knows where he is, or they claim not to know where he is,” Scorsese explained. “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.”
“Whitey Bulger…was…given kind of a carte blanche to do what he wanted in Boston,” Scorsese continued. “Jack heard that, and he said, ‘That’s interesting because then nobody knows where anybody stands.” Unfortunately for Nicholson, though, his performance didn’t go over well with Bulger. The deputy reported that the ageing mobster “shook his head in disgust many times while watching Jack Nicholson’s fictional version of him on the big screen.”
In the end, the deputy knew he had to make a move on Bulger, but because he was off-duty, he didn’t have his service weapon with him. By the time he made a quick trip to retrieve it and returned to the cinema, though, the slippery fugitive was long gone. He was eventually caught in Santa Monica on June 22nd, 2011, having survived the risk he took five years earlier to watch “himself” on the silver screen. He was 81 years old and had spent 16 long years on the run.
