Road to Perdition
In both the graphic novel and the film versions of Road to Perdition, Tom Hanks' character Sullivan (O'Sullivan in the book, but I'll stick to Sullivan here), on the run from his double-crossing mob boss Rooney, forces a wedge between Rooney and his Chicago ally Al Capone by robbing banks with their money. Sullivan shrewdly gives the bankers a share of the cash to ensure their silence.
The book has a poignant scene between Sullivan and his son Michael where he explains this money will be Michael's one day, to do with as he pleases.
Michael is overjoyed at the amount they have, especially since this takes place during the Depression, but Sullivan makes it clear it means nothing without their family, his wife and younger son, murdered by Rooney's son Connor.
I liked the film version, but thought, and still think, Hanks was miscast as Sullivan. The role needed a Clint Eastwood type. While Hanks can do tough-guy roles, I just wasn't convinced of him as a stone-cold killer, partly because of who he is. He's Tom Hanks! He wouldn't hurt a fly, would he?
If I was director Sam Mendes, I might have put Hanks in the Rooney role and had Daniel Craig play Sullivan, but that would've deprived us of a great performance from Paul Newman (one of his last, as it turned out) as Rooney, so maybe it's just as well.
In the introduction to the 1998 Paradox Press edition of Perdition, writer Max Allan Collins acknowledges how much truth there is to this tale: John and Connor Rooney (nee Looney) were real - a father and son who ran an organized crime business in the Iowa-Illinois Tri-Cities region.
Capone and Frank Nitti were real, obviously (Eliot Ness appears in the book too), and according to Collins, there was an actual enforcer whom Looney betrayed.
Perdition, however, is a work of fiction; for Collins, the fusion of fact and legend, as exemplified in films like Bonnie and Clyde, are what give it its strength:
...These things had really happened, right where I lived; there was a truth underlying the noir fantasy, more than moldy old books, musty magazines and library microfilm had ever brought to life for me... and that was where my impulse to develop what has been termed the "true-crime fiction" subgenre began.
Other movies about theft (an abbreviated list):
Across 110th Street
Bob le Flambeur