Issue: January 1995

Drew was just 19 when she posed for Playboy, but she'd already lived a rock-star life. And not the good kind of rock-star life—she was going to Studio 54 and doing coke as a pre-teen. She got her shit together, though, and today is a bankable star, but in 1995 she was still a wild child. It was around this time, you may recall, that she flashed birthday boy David Letterman on his talk show.