Kanye West got a reputation for being a bit of a sore loser at the Grammys, but at a certain point, it was hard to say it was unfounded. He lost Album of the Year three times in a row for his first three records, and each time, it was to artist who peaked creatively decades early. No disrespect intended to Ray Charles, an American icon and musical legend, but his late-period A&R'd-to-death Genius Loves Company is not a record on par with The College Dropout. Nor is U2's How to Dismantle an Atomic Bomb a bad record, but the band's creative peak was in the 1980s and 1990s; by 2006, Late Registration deserved to run the board. Perhaps the strangest of all was when jazz pianist Herbie Hancock—an incredible artist whose most celebrated work was released 40 years earlier—snagged Album of the Year over not just Kanye's biggest crossover smash Graduation, but Amy Winehouse's indelible Back to Black as well. Then, the 2011 Grammy Awards snubbed West's My Beautiful Dark Twisted Fantasy from the Album of the Year category entirely, to the surprise of onlookers everywhere.
Kanye West always loses AOTY to old people (when he's nominated at all)