The Oscars may be the belle of the awards-season ball, but—Björk aside—it isn't the place to take any risks on the red carpet. Nope, the good stuff seems to always come out at the Grammys, like Jennifer Lopez's attention-grabbing turn in that Versace dress in 2000, which put her on the fashion map.

Sometimes, taking a chance pays off. Fergie (above) opted to cover herself in little more than a sparkly tea towel in 2007 and got away with it.

Sometimes, the big reveal bombs. Pink might as well have fished her 2003 costume out of a bargain bin at Frederick's, while Sheryl Crow's 2005 Grammy dress looks like it did battle with a pack of moths...and lost.

Still, we're grateful for these looks we love to hate—at least they make us sit up and take notice. Rock on with your bad (taste) selves!