31. Whitney Houston
Most Infamous Moment: In a 2002 interview with Dianne Sawyer, when questioned about drugs causing her scary thin appearance, Houston responded, "Crack is cheap. I make too much money to smoke it...We don't do crack...Crack is whack."
Houston's ups and downs were constantly under public scrutiny; she was the one pop star everyone was rooting for to "get better." Despite her remarkable music career and impressive film resumĂ©, The Bodyguard actress' reputation was tarnished by her drug addiction and her poisonous relationship with husband Bobby Brown.