3rd Bass, "Gas Face" (1989)
Before he was the masked supervillain who "came to destroy rap" Daniel Dumile was the politically minded teenager Zev Love X of Long Island's KMD. Though they would go on to record two albums on their own, his first appearance was in the Yo! MTV Raps staple "Gas Face" by 3rd Bass, showing off the internal rhyme schemes that would gain him critical acclaim decades later. (Peep it: "Is I'm talkin coffee or cocoa, is you loco?/Cash or credit for unleaded at Sunoco.") His bandmate and brother, Subroc, passed away in 1993, and Zev Love X would go into hiding, only to emerge four years later as the iconic masked villain.