Whitey Bulger and Hollywood: Books, TV Shows, and Movies Inspired by the South Boston Crime Boss

From nonfiction books and adapted screenplays, to television episodes and a few too many upcoming biopics, Hollywood is thriving off of the image of Boston mobster Whitey Bulger, who is currently on trial, charged with 19 killings.

By | Arts & Entertainment |

whitey bulger

The Boston image portrayed in the media has come a long way since its hunky-dory Cheers days, and we have South Boston Irish mobster and mass murderer Whitey Bulger to thank for that. Bulger notoriously inspired many Boston-based crime dramas and books, and since his capture two years ago, is inspiring several more biopics.

With all the chaos currently surrounding Bulger’s trial, here is everything you should know about Whitey Bulger and Hollywood—from past, to present, and to future:

For 16 years, Bulger was on the run until he was captured, and in the meantime, a more ominous image of Boston surfaced in Hollywood. Films increasingly catered to stories that took place in Southie, Bulger’s crime location of choice, and he undoubtedly inspired filmmakers, producers, and writers to shed a more sinister light on Boston. It was this rebranding of the city, however, that brought some of the nation’s finest and iconic crime dramas to American audiences.

Movies Based on Whitey Bulger

The Departed

Image via The Departed / Facebook

The Departed, 2006

Directed by Martin Scorsese, this Oscar-winning movie has a cast of many household names—Leonardo DiCaprio, Matt Damon, Mark Wahlberg, and Alec Baldwin are among them. Jack Nicholson plays the fictional South Boston Irish mobster, Frank Costello, a character directly based on Whitey Bulger. Costello is a gangster working with law enforcement to sell out other gangsters, but simultaneously plants his own informant in the police department.

Untitled Project with Ben Affleck and Matt Damon

Well, who better to make a crime drama based in Boston than the two Boston guys who do it best. Damon and Affleck told GQ last year that they were excited to announce the partnership on their Whitey Bulger project. The plan is as follows: Damon will star as Whitey Bulger, Affleck will direct, and Terence Winter—writer of The Sopranos and Boardwalk Empire—will write the screenplay. “If it’s a straight biopic, we’ll do it over a period of time. But it’s always a question of what part of the story do you tell, and biopics are always a little cumbersome,” Damon said. “So do we find another way in? We’re still figuring it out.”

Black Mass

Black Mass is based on the book of the same title written by two Globe writers, Dick Lehr and Gerard O’Neill. Very recently, Johnny Depp dropped out of the film as the lead role of Whitey Bulger over a petty salary dispute (shame, shame, Depp). Supposedly, the script was written and shooting was ready to begin rolling before Depp’s dropout. No word yet on new casting.

Street Soldier with Peter Facinelli

Facinelli, best known for his role as the vampire daddy Carlisle Cullen in the Twilight saga, will produce this movie. The screenplay is based on the book titled Street Soldier: My Life as an Enforcer for Whitey Bulger and the Boston Irish Mob by Edward MacKenzie Jr. According to the Huffington Post back in 2011, Facinelli had the script written and ready to shoot prior to Bulger’s capture. It is now being rewritten.

“Untitled John Martorano” with Graham King and Chuck Hogan

Deadline reported years back that Chuck Hogan, whose book Prince of Thieves was turned into Ben Affleck’s box office hit The Town, has signed to write a script based on the Winter Hill Gang and its enforcer John Martorano. Supposedly, the pic will “chronicle the reign of the notorious criminal gang run by James ‘Whitey’ Bulger and the court case that exposed a corrupt relationship between the mob and the Boston office of the FBI.” Graham King, who won the Best Picture Oscar for The Departed, will produce the film.

Television Storylines Inspired by Whitey Bulger

whitey bulger

Image via Showtime

Brotherhood, 2006-2008

The Showtime TV series follows two brothers in Providence, one a politician and the other a gangster, who both living corrupt and secretive lives. Created by New Englander Blake Masters, the show is based on Whitey’s relationship with brother William, who was a huge political figure, a Democratic Party leader in Massachusetts, and a former president of State Senate from 1978-1996.

The 4th Reich, TBA

Showtime and Robert Di Niro are producing a crime-thriller series together about a neo-Nazi group out of a dominantly Irish neighborhood in South Boston. The project is currently in pre-production. The Showtime project is described as “American History X meets The Town. The central character is a former leader of the group who’s been released from jail to become an FBI informant.” Sounds a lot like Whitey has influence here.

Madso’s War, 2010

The Spike TV crime drama was about the Irish Mob of Boston. It was referred to as the “Irish Sopranos” during post-production, but unfortunately never got picked up. The show was loosely based on the sinister underworld of South Boston that Whitey left behind when he fled in the ’90s.

Untitled Peter Mehlman TV Comedy

Time magazine reported after Whitey’s capture that Seinfeld writer/producer Peter Mehlman is spearheading a comedy about a young couple that moves in next door to a mass murderer mobster—a character based on Whitey Bulger. The half-hour comedy does not feature Whitey as a character, but was inspired by the fact that Bulger was discovered living a life of leisure in Santa Monica for his 16 years of hiding. FOX reportedly purchased the comedy in 2011.

Books About Whitey Bulger

whitey bulger

Image via DickLehr.com

Black Mass by Dick Lehr and Gerard O’Neill, 2000

Written by correspondents at the Boston Globe, this book recounts Bulger’s story with his brothers and his crime scenes in South Boston during the ’70s and ’80s. As mentioned earlier, this book is being adapted for the big screen, the very same Bulger biopic that Johnny Depp will no longer be a part of.

Where’s Whitey? by Kevin Weeks and Phyllis Karas, 2010

This book is a combination of fact and fiction, written by Bulger’s former right-hand acquaintance Kevin Weeks. The book tells of the possibilities of Whitey’s whereabouts while in hiding for 16 years. It is also a follow-up of Weeks’s book titled Brutal, an account of his relationship with Whitey.

Falling for Johnny by Alison McLennan, 2012

Falling for Johnny is about the relationship between Johnny, a vicious gangster character inspired by Bulger, and Riley, a woman whose family were victims of Johnny’s criminal organization. “It’s not really about Johnny being a controlling bad guy. It’s about the people who fall for him. They fall for his charm, and quick money and bookmaking and drugs,” says author Alison McLennan. “And if somebody was looking to do a screenplay [on Falling for Johnny]—that’s the beauty of fiction. You can create the suspense and the drama without having to stay true to anything. You’re just inspired by real life.”

Whitey Bulger is just the kind of criminal that Hollywood’s been craving, to say the least, and now the overwhelming number of biopics in the works are projects that all of America are looking forward to seeing. So who will do it best? My money’s on Ben Affleck. (When is it not?)