21. Bob Dylan, 'Christmas in the Heart' (2009)
Christmas in the Heart is a great title for this utterly unexpected, weirdly inspired album – because with Dylan on the mic, it certainly isn't Christmas in the voice. In fact, his grizzled baritone is exactly what gives his 34th record a subversive charm: No music worships good singing like Christmas music, and by doing a carol like "The First Noel" or a post-War pop tune like "Christmas Island" straight and earnest, he makes you hear them with new ears. With help from musicians like Los Lobos' David Hidalgo and guitarist Phil Upchurch, he sings with real nostalgia as well as tender frailty, honoring this as vintage American music and making it part of his own story.