When: 1992

Kriss Kross may have been a one-hit wonder in the '90s, but the duo's ass-backwards contribution to fashion—no pun intended—will be forever remembered. Mac Daddy (R.I.P.) and Daddy Mac made teenagers think that wearing jeans backwards was a good look in the '90s (youthful rebellion or maybe the worst hip-hop decision ever, right up there with MC Hammer's pants). In 2013, Jermaine Dupri paid homage to the memory of Mac Daddy by wearing his Levi's backwards to Mac's funeral.