With The Girlfriend Experience, the recent film by Steven Soderbergh that screens today at the Gene Siskel, adult film star Sasha Grey attempts one of the trickiest maneuvers in show business—the move from porn movie trashiness to art film respectability.

(Then again, Grey already knows more than a few tricky maneuvers. Hey-o!) You can judge for yourself whether Grey’s acting chops will warrant future roles in mainstream films, but history shows that porn stars often have the odds stacked against them when they try spending more than five minutes on screen without doinking somebody. Decider looks back on how six other porn stars fared.