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 resumé, The Bodyguard actress' reputation was tarnished by her drug addiction and her poisonous relationship with husband Bobby Brown.