As a student at Margaret O'Brien's Charm School in Toledo, Holmes studies both modeling and acting. After attending a talent convention in New York City, she signs with a manager in L.A.
While still a senior in high school, Holmes lands a role in Ang Lee's The Ice Storm. She plays opposite Toby McGuire (left), and her part calls for her to pass out in his lap. The performance catches the eye of Kevin Williamson, who wants her to audition for his new show, Dawson's Creek.
In her mother's sewing room, Holmes records a home-video audition for Dawson's Creek. Williamson asks her to fly out to L.A. for a screen test, but Holmes declines; the trip coincides with her performance in her high school musical Damn Yankees. Williamson reschedules, and Holmes wins the part of girl-next-door Joey Potter, opposite James Van Der Beek, Michelle Williams and Joshua Jackson.
Dawson's Creek debuts on the WB. The show's creator intends for title character Dawson, played by James Van Der Beek, to anchor the show. However, Holmes steals the spotlight as witty and charming tomboy Joey Potter and is the only cast member to appear in all 128 episodes.
During filming of the first season of Dawson's Creek, Holmes and her Dawson's Creek costar Joshua Jackson, who plays Pacey Witter, have a brief romance. She considers Jackson her "first love." "It was something so incredible and indescribable that I will treasure it always," she tells Rolling Stone.
Holmes takes top billing in David Nutter's Disturbing Behavior as a girl from the wrong side of the tracks. She wins a MTV Movie Award for Breakthrough Performance Female in 1999 for her role.
Holmes starts dating American Pie's Chris Klein, a fellow Midwesterner. He is based in L.A., and the distance, combined with the pace of their film careers, proves difficult. "We don't see each other as much as we'd like," Klein tells PEOPLE.
Onscreen for six and half minutes in Wonder Boys, Holmes plays a coed temptress trying to seduce her aging professor played by Michael Douglas, who calls Holmes "a natural." She continues to break her wholesome image with her first nude scene in The Gift opposite Greg Kinnear (right). "I thought it was important to the scene and to the character," she tells GQ. "I just hope there aren't a lot of pauses on DVD players."
As the lead in Pieces of April, Holmes plays the black sheep in a family she eventually reconciles with over Thanksgiving dinner. The film is a critical success and earns raves. That May, Holmes leaves Joey behind as Dawson's Creek ends after six successful seasons, and in December she becomes engaged to Klein.
Holmes and Klein call off their engagement, and by April, the 26-year-old actress secretly goes out with 42-year-old movie star Tom Cruise. They have been dating for several weeks when they make their first public appearance in Rome at the David di Donatello Awards, the main national film awards in Italy.
BIOGRAPHY (top to bottom): Splash News; Warner Bros.; Screen Scenes; Tom Rodriguez/Globe; Everett; MGM; CHRIS HELGREN/REUTERS/Landov