PREVIOUS APPEARANCES ON THE TIME 100: 1
PRO: After a jolting breakup with his fiancée, West flew to Hawaii for a few weeks and returned with 808s & Heartbreak, a deep-digging confessional that had him singing instead of rapping. It was the riskiest album of his career, and it still managed to go platinum.
CON: His constant reminders of how awesome he is kind of take away from his awesomeness.
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