Whitey is heading for the big house and the tale of his notorious life is heading for the big screen.
James "Whitey'' Bulger, the longtime boss of the Winter Hill Gang, the Irish mob that ruled the Boston underworld for decades, is scheduled to be sentenced Wednesday in federal court. In August, a jury found Bulger guilty on 31 of 32 counts - including murder, extortion, money laundering, drug dealing and weapons possession.
The 83-year-old Bulger, who had spent 16 years on the run before being captured in Santa Monica, Calif., in 2011, won't be doing any more running. He will almost certainly spend the rest of his life sitting quietly behind bars.
One film about Bulger's life of crime is already in production. Producer/director Barry Levinson, who brought us "Diner," "The Natural," "Good Morning Vietnam" and "Rain Man," is working on "Black Mass," a film based on the book of the same name that chronicles Bulger's relationship with John Connolly, a disgraced FBI agent and fellow South Boston crony. Reports have been swirling that Ben Affleck and Matt Damon are also planning a film about Bulger, with Damon earmarked for the leading role.
When Whitey's story does hit the theaters, it won't be the first film about Irish gangsters. In fact, it won't even be the first time Bulger is portrayed on screen. In Martin Scorsese's Oscar-winner "The Departed," Jack Nicholson has the role of the vile Frank Costello, a character loosely based on Bulger.
Additionally, Irish criminals have been portrayed in prominent roles in a number of great movies – "Goodfellas," "On the Waterfront," "Mystic River," "The Sting," "Sleepers," to name a few. But those flicks don't exactly fit into the genre of Irish gangster films, as "The Departed" does.
While the preponderance of American organized crime movies have focused on the Mafia, there are a fair number of very good films about the world of the Irish-American gangster. Here's one man's top 10:
- Miller's Crossing (1990) – Gabriel Byrne plays the role of Tom Regan, the top adviser to Prohibition-era crime boss Leo O'Bannion (Albert Finney), who gets caught in the middle of a gang war between O'Bannion's Irish crew and the up-and-coming Italian mob. Directed by the Coen brothers, Joel and Ethan, this brilliant but underrated film had the misfortune of being released two weeks after the debut of Goodfellas, and was thus overshadowed.
- The Town (2010) – Ben Affleck directed this film based on Chuck Hogan's novel, "Prince of Thieves." Affleck portrays Doug McCray, a Charlestown bank robber who yearns to change his life and who falls into a romantic relationship with a bank manager he encountered on a heist, all while trying to elude the FBI.
- Kill the Irishman (2011) – Ray Stevenson gives a riveting performance in his portrayal of real-life Cleveland mobster Danny Greene, the labor leader turned gangster who survived a bevy of assassination attempts as his Irish crew, dubbed the "Celtic Club,'' went head-on against the Mafia in a deadly gang war in the 1970s. Like "Miller's Crossing," this movie boasts an all-star cast and is an underrated gem.
Page 2 of 2 - - The Departed (2006) – Director Martin Scorsese won Best Picture for this film about an undercover state police officer (Leonardo DiCaprio as Billy Costigan) who infiltrates the Boston Irish mob, all the while staying a step ahead of the mobsters' mole in the state police (Matt Damon as Colin Sullivan). A tremendous cast in a tremendous film.
- State of Grace (1990) – Sean Penn plays the role of Terry Noonan, who returns to his New York home after a 10-year absence and falls right in with his old friends in the West Side Irish mob. Little do his pals know that Noonan is a Boston cop brought in to be a mole in their crew. This film is inspired by "The Westies," T.J. English's brilliant non-fiction book about the Hell's Kitchen Irish mob. Gary Oldman provides a magnificent performance portraying Jackie Flannery, a character based on real-life Westies enforcer Mickey Featherstone. Like "Miller's Crossing," "State of Grace" was overshadowed by "Goodfellas," which was released the same week.
- Road to Perdition (2002) – Tom Hanks portrays Michael Sullivan, a Depression-era hit man for Irish crime boss John Rooney (Paul Newman), whose life takes a life-altering twist when his young son witnesses him commit a killing.
- The Friends of Eddie Coyle (1973) – Robert Mitchum portrays Quincy-based Eddie Coyle, a small-time hoodlum who decides to hand up his Boston crime associates to the feds in order to avoid a prison sentence. Eddie's friends turn out to be not so friendly.
- Gangs of New York (2002) – Set in 1863 Manhattan, Martin Scorsese directed this film about Amsterdam Vallon (Leonardo DiCaprio), who arrives in the Irish slum of Five Points to avenge the killing of his father. Daniel Day Lewis provides a sensational portrayal of Bill "The Butcher" Cutting, the crazed gang leader whom Vallon is targeting. A great cast.
- Angels With Dirty Faces (1938) – Fresh out of prison, Rocky Sullivan (James Cagney) returns to his Hell's Kitchen home and rekindles his friendship with his boyhood pal, Father Jerry Connolly (Pat O'Brien). As Sullivan grows friendly with the boys in the neighborhood, Father Connolly frets that the young men will emulate their hero and follow Rocky into a life of crime. The climax of this film provides one of the most chilling scenes ever.
- Monument Ave. (1998) – While this film did not do well at the box office, it is a personal favorite because of its uniquely Boston cast, setting and story. Denis Leary portrays a small-time Charlestown wiseguy, Bobby O'Grady, who must struggle with his neighborhood's renowned code of silence after his cousin is murdered by the brutal boss of Bobby's crew (Colm Meaney as Jackie O'Hara).