Conversation so far:
What were some of Weird Al Yankovic's parodies?
White & Nerdy is the second single from Weird Al Yankovic's album Straight Outta Lynwood. It parodies the song Ridin' by Chamillionaire and Krayzie Bone.
Did White & Nerdy by Weird Al Yankovic win any awards?
Both White & Nerdy and Straight Outta Lynwood were certified gold, and later platinum, by the RIAA, the first time any of Weird Al Yankovic's singles has been certified platinum.

Question: How did he start doing parodies?
Self-contained rewrite: How did Weird Al Yankovic start doing parodies?