When: 1990-1993

When Pitt started to get regular work, he was inarguably handsome, but his leading-man potential was unclear. Two of his best-received performances were as slimebag criminal boyfriends, in the TV movie Too Young to Die? (1990) and the theatrical release Kalifornia (1993). Both were made with wild-child Lewis—literally a child, as she was 16 when they started dating.

Brad ended up going down the path of stardom suggested by A River Runs Through It, but you have to wonder who he'd be if he had stayed with Lewis. Perhaps the Mickey Rourke of his generation? Alas! We'll never know.

Smash Probability: Due to the laws regarding age of consent in various states, we must respectfully decline to answer this one, your honor.