Certain actors thrive when playing heroes. Tom Cruise, Chris Evans, Bruce Willis, Harrison Ford … they are most comfortable when playing the good guy. 
 
Brad Pitt often prefers being bad. Sometimes psychotic. This doesn’t define him or his career. But Pitt spends more time occupying cloudy moral areas, often unearthing fascinating character portrayals. 
 
Pitt once again plays a hardened criminal in Andrew Dominik’s Killing Them Softly, which opens Friday. His character, Jackie Coogan, is hired to hit a rival crime gang after they decide to steal from a high-stakes neighborhood card game. As usual, Pitt surrounds himself with major talent in supporting roles. But the focus is on Pitt playing a bad guy once again. 
 
It got us thinking about Pitt’s finest criminal roles. We’re going with five. Tell us if you have a favorite, or if we missed anybody.
 
1. Tyler Durden, Fight Club
Arguably Pitt’s most popular role – ironic, since his character doesn’t exist. Spoiler alerts shouldn’t be necessary at this point. We all know that Tyler Durden was the devil sitting on Edward Norton’s shoulder, inspiring him to anarchy as David Fincher’s revolutionary drama came to an explosive finale. Contrary to popular belief, the second rule of Fight Club says that we can’t stop talking about Pitt’s performance. 
 
 
 
2. Jesse James, The Assassination of Jesse James by the Coward Robert Ford
Pitt’s first collaboration with his Killing Them Softly director, Dominik, cast the handsome A-lister as the famous (and infamous) train robber. And while some might argue that Pitt was overshadowed by his co-star (the hero-worshipping Casey Affleck) or by Roger Deakins’ breathtaking cinematography, Pitt’s subtle turn as one of the world’s most recognized men acts as the glue that holds this long production together. 
 
 
3. Early Grayce, Kalifornia
An early role for Pitt, yet one of his most terrifying. And we're not just talking about the greasy hair and the trucker's cap Pitt sports throughout Dominic Sena’s road-trip thriller. The actor plays a parolee who hitchhikes with a journalist (David Duchovny) who happens to be researching serial killers. As the film unfolds, you learn Pitt IS a killer, triggering a murder spree that pulls the reporter and his photographer girlfriend (Michelle Forbes) into his personal hell. 

 
 
4. Rusty Ryan, the Ocean’s franchise
Criminals don’t have to be all sneers, jeers and vicious threats. Sometimes they are smooth-talking, well-dressed casino robbers who are always hungry. (Watch Pitt in the Ocean’s movies … dude’s constantly eating something). Steven Soderbergh’s Ocean’s ensemble overflows with charisma. And yes, ladies, the men are easy on the eyes. But we’ll always adore the interplay between Pitt and his real-life close friends, George Clooney and Matt Damon. 
 
 
5. Joe Black, Meet Joe Black
OK, fine, Joe Black wasn’t necessarily criminal. But he was the Angel of Death, and that’s dark enough to make our list. Also, Martin Brest’s somber, sentimental meditation on death gets a bad rap, but Pitt, Anthony Hopkins and Claire Forlani are so open-hearted and honest in the film that we beg you to give it another chance. To ignore it would be … well, criminal.
 
 
 
Follow along on Twitter @Sean_OConnell and @Fandango.