Whitey Bulger's Casting Call

The Boston Globe‘s gripping play-by-play of the arrest of Whitey Bulger in this Sunday’s paper had all the elements of a Hollywood crime thriller: an Icelandic beauty queen tipster, a hipster rocker who collaborates with police, a homeless man duped into sharing his identity, trips to Tijuana for pills and Santa Monica farmers markets for dried apricots and nectarines, and a cat named Tiger who tied it all together.

Bulger’s already been the basis for one film, The Departed, and news came out this summer that a new movie, based on the book “Street Soldier” and produced by Twilight actor Peter Facinelli, is in the works. But as the lineup of characters is beginning to be fleshed out further, it’s time to speculate as to which stars Hollywood will cast.

Whitey Bulger: Dabney Coleman has been doing a fair turn as a crime boss in Boardwalk Empire, HBO’s series about Atlantic City’s criminal underbelly during prohibition. (He also played Tom Hank’s philandering dad in You’ve Got Mail.) Sean Connery is another obvious choice, he’s got the beard, and it’d be fun to watch the ultimate Bond take on the role of a hardened criminal.

Catherine Greig: Helen Mirren could do a turn as the silver-haired cat-lover Greig, but Meryl Streep, Annette Benning, or Judi Dench could also be fabulous. Streep may actually get bonus points for the physical similarity. Imagine her with a short haircut … it’s not that much of a stretch.

Anna Bjornsdottir: The Icelandic beauty queen already bares a striking resemblance to Diane Keaton, at least from the few photos published of her yesterday.

Joshua Bond: The 28-year old building manager in Bulger and Grieg’s apartment complex, who’s also in an country band, collaborated with the FBI to ensnare Bulger in his building’s garage, coming up with a ruse that a storage locker had been burglarized. Jake Gyllenhaal seems to have both the country and criminal aspects of the role down, but Mark Ruffalo, in his always-clueless “How did I get in the middle of this?” way, could inject some unforeseen humor into the role.

Who’s going to play the bumbling FBI agents? The intrepid reporters who connect all the dots? Have other suggestions for the cast? Let me know in the comments.