TIM ROBBINS & SUSAN SARANDON
Though famous for their political activism and their smoldering scenes together in Bull Durham, Tim Robbins and Susan Sarandon are arguably just as famous for having had a high-profile Hollywood romance—and two children as the results of it—without ever getting married. During the course of their 21-year relationship, they became one of the industry's most recognizable couples, but mutually decided never to tie the knot—since they broke up in 2009, maybe they made the right choice. Robbins won a Best Supporting Actor Oscar in 2004 for Mystic River, and was nominated in 1996 for directing Dead Man Walking; Sarandon took home her Best Actress gold that same year for the same film, and she'd been nominated on four previous occasions.
WARREN BEATTY & EVERYBODY
It's a little unfair to include Warren Beatty on this list; he's probably slept with every female Academy Award winner since 1960. But he definitely belongs, and he made it easy on us by dating a few high-profile superstars who matched him Oscar for Oscar. Beatty—who won a Thalberg award and a Best Director Oscar in 1982 for Reds, as well as six other nominations—has been romantically involved with the likes of Julie Christie (three nominations and a Best Actress win in 1966 for Darling) and Diane Keaton (three nominations and a Best Actress win in 1978 for Annie Hall).