Witherspoon breaks into modeling and lands an acting gig at age 7, shooting a TV commercial for a florist. She continues doing local commercials and takes first place in a Ten-State Talent Fair at age 11.
The Nashville debutante develops her confidence while attending an all-girls high school. "I really believe in single-sex education," she tells PEOPLE in 2002. "There are no inhibitions. You can walk to school with your zit cream on and your hair in rollers and nobody cares."
At 14, Witherspoon debuts in the coming-of-age drama The Man in the Moon, giving her first onscreen kiss to costar Jason London. She makes her television premiere the same year in the Diane Keaton-directed drama Wildflower.