Year Arrested: 1999

Crime: Drunk driving.

Imagine you're one of the greatest workers your company has ever seen, but there's always a guy who outshines you and gets all the glory and dough while you solidly plug away year after year. Of course you're going to have a few drinks when you're off-the-clock! That's how Pippen must've felt in 1999 when he was arrested for pulling into the opposite lane to drive around cars stopped at a red light. The t-shirt under the blazer is a classic late '90s move, as is the hoop earring that Scottie (and, of course, Jordan) was known for.