9. Best New Artist (1981): Christopher Cross Sails Away With Grammy Gold
The 1981 Grammys were all about Christopher Cross. In a feat never matched before or since, the Yacht Rock king walked away with Record of the Year, Album of the Year, Song of the Year and Best New Artist. He beat out the Pretenders, Irene Cara, Robbie Dupree and Amy Holland for the latter award. Sadly, the evening was the peak of his career, though later that year he did release "Arthur's Theme (Best That You Can Do.)" He does remain a popular live act and his performance of "Ride Like the Wind" with the Roots on Late Night With Jimmy Fallon a couple of years back was one of the great moments in the show's history. The dude is a sick guitarist. Seriously.