Debra Messing
Debra Messing is known for her roles in the shows Will & Grace, Ned and Stacey, and Prey as well as movies including The Wedding Date and Along Came Polly. But before she got her big break, she was simply a high school student who starred in the school’s productions of Grease and Annie.

Messing chose a long white gown for her prom dress, and paired it with some voluminous curly hair. Her date wore a suit and tie, and the two looked happy as they strolled arm in arm. In a weird way, although she’s changed quite a bit since her high school days, the actress actually looks older in her prom pic, but that’s probably just the old-fashioned clothes and hairdo.