When: 1989

Brad Pitt was still finding a foothold in Hollywood and fumbling around with famous babes in 1989, when he briefly dated Applegate. She, of course, was a mega-star, having endeared herself to high school boys everywhere playing TV's favorite sexy daughter, Kelly Bundy on Married With Children. When the pair showed up at the 1989 MTV Movie Awards, viewers had to be told the identity of this studly young fellow. Many years later, Applegate expressed regret at having left the awards show with someone else.

Smash Probability: Applegate said the relationship evolved from "just friends" to something more, and then quickly ended. Is it possible they didn't do it? No, that's not possible.