The 51st Grammy Awards ceremony, held last night in L.A. at the Staples Center, could go down as one of the most hip-hop friendly (read: least boring) ceremonies we've watched in a good minute. Jay-Z, T.I., Lil' Wayne and Kanye all held it down with their respective performances. So much so that we thought the powers that be would drop a gold gramophone on 'em for Album of the Year.
Truth be told, we all thought Weezy'or at least Coldplay or Radiohead'would take home the award. But when Allison Krauss and Robert Plant got called up to the stage, you could almost hear the collective "what the fuck?" This isn't the first (nor will it be the last) time the Grammy board gives their most prestigious award to an artist who hasn't made culturally relevant music for 30 years. Take a look back at five of the most head scratching moments in Grammy history...
2008 
• WHAT WON: Herbie Hancock River: The Joni Letters
• WHAT SHOULD HAVE WON: Kanye West Graduation
• WHY: We have nothing against Herbie Hancock, but not only did dude go into the ceremony with 10 Grammys already on his mantle, his 47th album wasn't even full of original work, it was a Joni Mitchell cover album! So the Grammy board would like you to believe that Herbie covering Joni is better than Amy Winehouse's breakthrough sophomore album and Kanye's best album to date. Right. They obviously haven't been in a club when "Flashing Lights" comes on.
2007
• WHAT WON: Dixie Chicks Taking the Long Way
• WHAT SHOULD HAVE WON: Justin Timberlake Futuresex/LoveSounds
• WHY: Along with being JT's Thriller, Futuresex/LoveSounds was the album that every R&B artist attempted to make. We don't know anyone who still talks about, plays or tries to recreate Taking the Long Way.
2005
• WHAT WON: Ray Charles Genius Loves Company
• WHAT SHOULD HAVE WON: Usher Confessions
• WHY: We get it, it was Ray Charles' year. But that was no excuse to snub Usher's melodrama of an album, which was also the best R&B effort in years and sold 1.1 Million its first week. Now that he's wifed with children, Usher is never going to be able to top his platinum in a week opus. Well, unless he pulls an Usher (and by that we mean, he gets divorced and writes and album about the divorce).
2002
• WHAT WON: O Brother, Where Art Thou? Soundtrack
• WHAT SHOULD HAVE WON: Outkast Stankonia
• WHY: It may not count for much, but there's a reason why Stankonia (the last real Outkast album) made it onto TIME magazines 100 best albums of all time list and no one can remember who exactly was on the O Brother, Where Art Thou soundtrack.
2001
• Who Won: Steely Dan Two Against Nature
• Who Should Have Won: Eminem The Marshall Mathers LP
• WHY:This Steely Dan win was definitely retribution for the fact that they've never won a Grammy. Cool. But did they need to deny Em the award for his magnum opus? Maybe they'll give it to him when Relapse finally comes out in 2025.
