Pitt won his first of two sexiest awards in 1995 while he was dating Gwyneth Paltrow. (That all-star-couple element seems to be a ticket into the sexy club.) That year, he also starred in the sci-fi film "Twelve Monkeys" and psychological thriller "Se7en," but he was clearly in the running for the title after his sexy roles the previous year in the Western drama "Legends of the Fall" and the horror film "Interview With the Vampire."