1. “White & Nerdy” (2006)
“White & Nerdy” is a minor miracle of sorts. Well into his third decade as a performer, “Weird Al’’ Yankovic claimed his first-ever Top 10 hit with this parody of “Ridin’,” a hip-hop anthem from Chamillionaire and Krayzie Bone. He reached such heights because he not only adapts to current fashion, he’s sharpened his skills as a writer over the years: the jokes on “White & Nerdy” are specific, detailed and stand apart from the satire. Of course, they’re meant to be heard as this booming, bass heavy single, where Yankovic manages to nail the speedy cadences of Charmillionaire without seeming patronizing. Ultimately that’s the key to his long-lasting success: his parodies come from affection, not anger.
Read More: Ranking Weird Al Yankovic’s 25 best songs and parodies