20. Carrie Underwood

Well, here's Carrie Underwood giving the 'Rachel from Friends' look a try. We think she rocks it! We're just a little sad that we only have this grainy black and white photo to judge it by. We hope she didn't destroy all the evidence from her prom night. Everybody had 90s hair once, and Underwood doesn't have to be ashamed of it!

The photographer has done Underwood something of a disservice here. This picture should all be about her - it's her big night, after all! Instead, her date dominates the scene, pushing her to the fringes. Maybe there are better photos of this evening somewhere within the Underwood household, safely under lock and key so people like us can't get our hands on them!

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