The Rapper: Drake
Nominated For "Best New Artist" At: The 2011 Grammy Awards
Beat Out By: Esperanza Spalding
Why He Should Have Won: Spalding's victory on Grammy night was huge for the jazz community. But, let's be honest: If you look back at the year leading up to the 2011 Grammys, no rappers, rookie or veteran, had an impact like the one that Drake had. So, it's a crime that he didn't get rewarded for it.