"Weird Al" Yankovic
The undisputed king of the rock song parody, Yankovic has been inducing cringes and laughs in equal proportion since the early 1980s. Not an especially gifted singer (to put it politely), he relies instead on cornball puns, clever videos and sheer trial and error. After a string of '80s classics like the Michael Jackson takeoffs "Fat" and "Eat It," things started to look a little ugly, as anyone who saw the film UHF can attest. Undaunted, he bounced back with '90s efforts such as "Smells Like Nirvana" and the Coolio parody "Amish Paradise." In 2006, after once again losing his clout as a pop culture commentator, a parody of Chamillionaire's "Ridin'" (as "White and Nerdy") landed Al in the top 10 for the first time ever. He's best taken in small doses -- sitting through an entire CD might be considered the musical equivalent of cooling off on a 95 degree day with a glass of warm gravy. Still, whether he's busting out schwag rhymes about computer software ("It's All About the Pentiums") or resurrecting unwelcome oldies (the "Jurassic Park" parody of "MacArthur Park"), Weird Al proves that stupidity, when used wisely, can truly be a virtue.