5. "Fat" (1988, Michael Jackson's "Bad")
No other artist has provided Weird Al with more spoof-worthy material than the iconic Michael Jackson. Specifically, the King Of Pop's post-Thriller statement "Bad" is a comedian's wet dream. But rather than play up the ridiculousness of a hooded MJ channelling his inner-thug, Al broke left and sped down the road to sophomoric cheekiness. "Fat" is the kind of politically incorrect, brazenly wrong number that could never be released today ("Your butt is wide, well mine is too/Just watch your mouth or I'll sit on you..."). Which makes the song even more of a guilty pleasure.
4. "Smells Like Nirvana" (1992, Nirvana's "Smells Like Teen Spirit")
The late Kurt Cobain was not known for his cheery optimism. But the transformative frontman of Nirvana still had a biting sense of humor. Not only did Cobain give Weird Al the green light to cover his band's groundbreaking single, he wore the delirious jab as a badge-of-honor as proof that the grunge innovators had finally made it.
3. "Eat It" (1984, Michael Jackson's "Beat It")
Another Michael Jackson nod and arguably Weird Al's most beloved parody, "Eat It" transformed the amusing oddity into a mainstream star. The gag track won a Grammy Award for Best Comedy Recording and peaked on the Billboard charts at no. 12, Al's highest positioning until more than two decades later.
2. "Amish Paradise" (1996, Coolio's "Gangsta's Paradise")
Coolio was none too pleased when Weird Al took on his sobering tale of gangsta life, prompting Yankovic to write a personal letter of apology to the West Coast rapper. Years later, Coolio admitted that "Amish Paradise" was pretty damn funny. We wholeheartedly agree.
1. "White & Nerdy" (2006, Chamillionaire's "Ridin")
Weird Al's biggest charting hit and the veteran act's first top 10 single is also his most impressive artistic effort. Yankovic should never be confused as a topflight MC, but he gamely flips Chamillionaire's and Krayzie Bone's rapid-fire lyrics. "Spend my nights with a roll of bubble wrap/Pop pop, hope no one sees me gettin' freaky/I'm nerdy in the extreme and whiter than sour cream." Good night, folks.