10. Tony Bennett & Amy Winehouse (2012) - 'Body and Soul' won unexpectedly for Best Pop Duo,Group Performance.
9. Esperanza Spalding (2011) - Best New Artist over Justin Bieber.
8. Bobby McFerrin (1989) - 'Don't Worry, Be Happy' won Song of the Year.
7. Steely Dan (2001) - Album of the Year win for 'Two Against Nature'
6. Herbie Hancock (2008) - Album of the Year win surprised many.
5. Macklemore & Ryan Lewis (2014) - Beat Kendrick Lamar for Best Rap Album.
4. Christopher Cross (1981) - Swept major categories over established artists.
3. Bon Iver (2012) - Won Best New Artist despite being relatively unknown.
2. Jethro Tull (1989) - Beat Metallica for Best Hard Rock, Metal Performance.
1. Milli Vanilli (1990) - Won Best New Artist, later found they didn't sing on their album.