Debra Messing
Debra Messing, acclaimed for her roles in television shows like “Will & Grace” and “Ned and Stacey,” as well as movies including “The Wedding Date” and “Along Came Polly,” was once a high school student who actively participated in her school’s productions of “Grease” and “Annie.”

Messing chose a long white gown for her prom dress and complemented it with voluminous curly hair. Her date wore a suit and tie, and the two looked joyous as they strolled arm in arm. In a peculiar way, although she has transformed since her high school days, the actress actually appears older in her prom photo, likely owing to the old-fashioned clothing and hairstyle.