Not necessarily a movie you'd expect to see on a list of Pitt's best shirtless roles... In this drama, Pitt plays Rick, a strapping young man diagnosed with a horrible disease that will cause him to die within three days if exposed to the sun. Best to overlook the glaring question of how exactly Rick got quite so tan and toned if all he does is sit around in the dark -- apparently there isn't much to do in there besides work on his abs. The suspension of disbelief this one requires keeps Rick at the bottom of the list.

Dark Side of the Sun, Guy Boyd, Brad Pitt 1997. Photo Courtesy of The Everett Collection