Don’t Be Cruel

With 1988’s Don’t Be Cruel, Bobby Brown transformed himself from a teen idol into a seductive crooner with a rapper’s brash self-confidence. Overseen by producers Babyface and L.A. Reid, “Don’t Be Cruel” and the unapologetic “My Prerogative” pair Brown’s sneering-but-sexy attitude with hip-hop’s rugged breakbeats. Even the slow jams—“Roni,” “Rock Wit’cha”—conceal sharpness beneath Brown’s smooth delivery. Rap, pop, and soul converge on “Every Little Step,” a dazzling hit that proves R&B doesn’t have to be corny to be catchy.