16. Herbie Hancock Winning Album of the Year over Amy Winehouse & Kanye West

Year: 2008

Both Amy Winehouse's Back to Black and Kanye West's Graduation were up for the award but lost to Herb. Granted, Herbie Hancock's tribute to Joni Mitchell was a solid piece of work. But good grief, Amy's record was a game-changer. And we totally wouldn't have minded if Kanye stormed the stage to claim the gramophone that year.