48. Andre Nickatina
From: San Francisco, CA
Signature Song: Andre Nickatina "Smoke Dope and Rap" (1993)
A hero in his native Fillmore District of San Francisco, as well as a regional star throughout the West Coast, Andre Nickatina is known to most as the artist behind crossover cult hit "Ayo for Yayo," even though the song is more of a feature for fellow San Franciscan San Quinn. But Nickatina's catalog is deep, with two decades in the business and a career's worth of classic, unusual music.
Initially known as Dre Dog, Nickatina's first two albums both made some noise on Billboard. After his 1997 name change he released a series of records that would develop his cult fanbase, beginning with that year's Cocaine Raps, 1998's Raven in My Eyes. and 1999's Tears of a Clown. He was also a significant collaborator, releasing several records with San Fran rapper Equipto and helping launch the career of the Mob Figaz with the flawless Mob Trial compilation.
An unapologetically louche rapper with an eccentrically mannered flow, Nickatina's unusual musical choices are epitomized on his 2003 album Conversation With a Devil, when he first transitioned from Fillmore rap scene mainstay to dorm room stoner eccentric. The playful opening title track sets the stage for a record that alternates between Ren Faire production and bagpipes, a perverse, oddball sense of humor, and moments of genuinely intense revelation, like the harrowing morality tale, "Soul of a Coke Dealer."