63. Kanye West, '808s and Heartbreak'
In 2008, pop went bonkers for Auto-Tune, and on his fourth album, Kanye West jumped on the cyborg soul bandwagon, largely forsaking rapping to (kinda sorta) sing the blues. (West's mother had recently died and he had just split with his fiancée.) The results were occasionally gauche, and always monumentally self-pitying. ("How could you be so heartless?" he sobbed.) But no one before or since has wrung so much pathos from Auto-Tune; West sings in the voice of a man so stupefied by grief that he's become not quite human.
• Rolling Stone's Original 2008 Review