Amy Winehouse's shocking upsets made Grammy history [Video]
She entered the contest with six nominations, but was expected to win just three. Most pundits predicted she'd bag best new artist in a close contest with Taylor Swift and that she'd fend off Christina Aguilera ("Candyman"), Fergie ("Big Girls Don't Cry") and Nelly Furtado ("Say It Right") to claim best female pop vocalist for "Rehab." In the race for best pop vocal album, odds were good that her "Back to Black" CD would squash Maroon 5's "It Won't Be Soon Before Long," but it wasn't a sure thing.
In the end, she won all three.
However, pundits weren't eager to stick out their necks for Winehouse in the top Grammy contests. In the past, those prestigious honors had never been won by music's trash divas like Madonna. Most Grammy gurus believed "Rehab" would lose best record and song to Rihanna's "Umbrella." They were wrong. Ultimately, the only contest Winehouse lost was for best album. "Back to Black" was expected to lose to Kanye West's "Graduation," but -- surprise -- both got trounced by Herbie Hancock's "River: The Joni Letters."
At the end of Grammy night, Winehouse tied Lauryn Hill, Alicia Keys, Norah Jones and Beyonce for the record of achieving the most wins by a female artist in one year. Beyonce would claim that crown solo in 2010 by winning six.
Below, Winehouse at the 2008 Grammys accepting the award for best record of the year from Tony Bennett and Natalie Cole via satellite from London.
-- Tom O'Neil
Photo: The "Back to Black" CD cover. Credit: Republic Records