Top 10 Biggest GRAMMY Upsets Of The Past 10 Years (billboard.com)

8th GRAMMY Awards (2006)
BEST RAP/SUNG COLLABORATION: Jay-Z & Linkin Park, "Numb/Encore"

Jay Z is no stranger to GRAMMY acclaim -- he's nominated for nine awards at the upcoming ceremony, after all -- but the fact that his rap-rock single with Linkin Park earned him an award is pretty mind-blowing in retrospect. The single from the collaborative album Collision Course actually won more GRAMMYS than Jay Z's "Encore," from The Black Album, and Linkin Park's "Numb," fromMeteora; the song also trumped hits by Destiny's Child, Ciara and Gwen Stefani & Eve ("Rich Girl") in the process.