WORST: Kate Hudson attempted a Western-style look in 2001, wearing her blond hair in tight curls, pulled back into a horrific updo. Blue eye shadow did nothing to help the failed look.

WORST: Heidi Klum rocked a double pouf in 2008—pre Snooki!

WORST: From the teased updo to the purple eyeshadow, Lisa Rinna looked like she belonged in a Las Vegas show at the Awards in 2009.

BEST: The subtle addition of purple eyeliner in 2009 made Natalie Portman’s eyes pop.

BEST: Taraji P. Henson looked tres sophisticated in 2009, skillfully parting her short hair on the side, and opting for the dark eyes/nude lips look.

WORST: Jessica Biel looked like she hadn’t slept for days when she showed up to the Oscars in 2009. Her frizzy hair refused to be tamed, while her makeup completely washed her out.

BEST: Kate Winslet looked impeccably flawless, opting for reddish-toned lipstick and eye shadow, and a pulled back ‘do in 2009.

WORST: Parting her hair straight down the middle was not a great choice for Sarah Jessica Parker in 2009.

WORST: At the 72nd Annual Academy Awards Angelina Jolie looked like Elvira, wearing her jet-black hair below her waist, and giving herself pungent, black cat-eyes.

BEST: Salma Hayek looked smoldering, going for a dramatic, smoky-eye/nude lips look, and sweeping her dark hair back into an updo in 2005.

BEST: Michelle Williams was a refreshingly ravishing in 2006, showing off her perfect pout in red lipstick and opting for a gracefully sleek updo.

WORST: Tilda Swinton’s orange-red hair was an awful start to her Oscar beauty. The actress opted for a completely fresh-faced look, wearing absolutely no makeup!

WORST: Calista Flockhart looked like she hopped out of the shower and threw her hair up without looking in the mirror at the Oscars in 2008.

BEST: Jennifer Aniston was a true California girl in 2009, looking sun drenched and sexy.