Bon Iver (2011)
Has anyone looked so tortured at the idea of winning a Grammy? (And he refused to participate in the ceremony's Beach Boys homage. Go get 'em, tiger.) Justin Vernon may be the most obscure artist to get nominated for BNA, much less win, but that just makes him part of this gloriously nonsensical Grammy tradition. And his finest song, "Beth/Rest," sounds exactly like Christopher Cross, so this means a de facto second Best New Artist win for C.C. Always bet on Christopher Cross. Always.