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.
A newbie to red carpet functions, Witherspoon attends a tribute to Al Pacino on the arm of actor Chris O'Donnell, Pacino's Scent of a Woman costar. Attempting to nip rumors in the bud, O'Donnell's rep tells PEOPLE, "Chris really likes her," adding, "They're just friends."
Before graduating high school, Witherspoon appears in three more films this year, winning her first lead role in A Far Off Place. "She has charisma and that 'thing,'" Marshall Herskovitz, her director in 1993's Jack the Bear, tells PEOPLE. "The camera loves her; she is down to earth and sexy."
In a fortuitous first meeting, Witherspoon takes note when a mutual friend brings actor Ryan Phillippe to her 21st birthday party. "I think you're my present," the actress tells Phillippe, reports PEOPLE. Both acknowledge an intense initial emotional connection; after five weeks of phone calls, letters, and e-mails, the two go out on their first date, moving in together soon after.
Costarring with then-boyfriend Phillippe in Cruel Intentions was a trial. Witherspoon tells Entertainment Weekly, "I had to see him make out with a lot of really cute chicks. That was definitely difficult."
Critics gush about Witherspoon's sharp comedic turn in Election (opposite Matthew Broderick) as go-getter Tracy Flick, gunning to become student council president. Says New York Times critic Janet Maslin: "Ms. Witherspoon, narrowing her eyes into slits whenever Tracy is thwarted, charges through the film with all due comic monstrousness and turns her character into somebody everyone knows."
A summer wedding follows their December engagement, and a six-months-pregnant Witherspoon, 23, and Phillippe, 24, marry on a plantation near Charleston, S.C. That September, Witherspoon gives birth to daughter Ava. "There's nothing better to me than being at home on a Friday night and eating pizza, watching movies or hanging out with Ava," she tells PEOPLE.
Grossing a surprise $140 million, the film Legally Blonde catapults Witherspoon to leading-lady status. "Part of what I love about Elle [her character] is she's fun," Witherspoon tells PEOPLE. "She's laughing and she's girly and she likes to have her nails done. But she's also successful and ambitious." The 2003 sequel, Legally Blonde 2: Red, White & Blonde, earns the star a $15 million paycheck.
BIOGRAPHY (top to bottom): RUSS HARRINGTON; Splash News; Samuel Goldwyn/Everett; Ron Galella/Wireimage; Steve Granitz/WireImage; Bob Frame; Bob Akester; David Rohmer/X 17; Sam Emerson/MGM