4. Boyz II Men "Motownphilly" (1991)
Producer: Dallas Austin
Picture this: Four dudes from Philly form a New Jack Swing group, but instead of wearing jewelry, bomber jackets, and shades, they're dressed in cardigans, bifocals, and bow ties in their first "New Jack" video. They would go on to become one of the most successful groups of the '90s. This isn't the punchline. This was Boyz II Men, and the single—"Motown Philly"—was one of the decade's greatest. Never mind the preppy outfits; Boyz II Men meant business.