1. Bobby Brown "My Prerogative" (1988)
Album: Don't Be Cruel
Producer: Bobby Brown, Gene Griffin, and Teddy Riley
In "Don't Be Cruel," Bobby Brown played the role of a helpless lover with a vulnerable heart. It was a good song, but he really took control in the very next track—"My Prerogative." With this track Bobby Brown shed his boyish New Edition image and become a full-fledged icon who remains on many of our playlists today. Raw, nasty, and over-the-top, "My Prerogative" was a track that everybody could get down to.