Photographer Jeff Dunas spots 16-year-old Diaz at a party and offers to help her land modeling work. Within days she has a contract with Elite and shortly thereafter is working for clients such as Coca-Cola and Nivea. "She has an energy, an electricity in her face, a sparkle that is unmistakable," Dunas tells PEOPLE in 1998.
While shooting an ad for L.A. Gear, Diaz falls for video producer Carlos de La Torre, 27. "I spent the entire day trying to get him to talk to me," she tells PEOPLE in 1994.
Diaz hits the big screen in the Jim Carrey comedy The Mask. The model, whose only acting experience was in a high school drama class, "tried out as a joke," according to her agent, Robin Levy. Diaz lands the part after 12 callbacks. Still, "the first day was hell," Diaz tells PEOPLE. "When Carlos was driving me to the studio it was like, 'Babe, pull over. I'm going to throw up.'"
After ending her relationship with de La Torre, Diaz goes on to date Matt Dillon for two years. The couple met while filming in Minnesota (his, Beautiful Girls; hers, Feeling Minnesota). "I love him incredibly," she tells Britain's Guardian in 1997.
Diaz appears as Julia Roberts' annoyingly-perfect nemesis in the romantic comedy My Best Friend's Wedding, which eventually earns $127 million. In addition to the blockbusters, Diaz takes roles in smaller films, such as Head Above Water with Harvey Keitel.
After being named one of PEOPLE's 50 Most Beautiful, Diaz takes a gross-out comedic turn in There's Something About Mary. The movie becomes a smash hit, earning $172 million, and the hair-gel joke makes movie history. Diaz only agreed to the scene after long negotiations – and a couple of beers, the film's co-director Bobby Farrelly told PEOPLE. "She was thinking, 'I have a career going here, guys, and I don't want to ruin it over one of your ridiculous gags.'"
It's a new look for Diaz in Being John Malkovich: The actress dons a mousy brown wig and contact lenses to play the dowdy Lotte Schwartz opposite John Cusack and the film's namesake in the indie directed by Spike Jonze. PEOPLE calls the flick a "fabulously bizarre comedy, a dizzy original."
After a quiet breakup with Dillon, Diaz begins a low-profile romance with actor and 30 Seconds to Mars frontman Jared Leto. The couple will later dodge wedding rumors, first sparked when Diaz wears a $15,000 ring of rose-cut diamonds to the 2003 Golden Globes. Their relationship lasts four years.
Diaz joins Lucy Liu and Drew Barrymore in Charlie's Angels. "I laughed every day I went to work. I got to kick ass. I got to drive fast cars and fast boats. I got to laugh my ass off. I got to dance my ass off. And I got paid to do it," she tells tells Harper's Bazaar. They all return for Charlie's Angels: Full Throttle in 2003, which features Demi Moore and grosses more than $100 million.
Shrek premieres and a franchise is born. Diaz voices the object of the ogre's affection, Princess Fiona. In April, Diaz accepts the Nickelodeon Kids' Choice Award for Best Burp (as Princess Fiona). She signs on for 2004's Shrek 2 and 2007's Shrek the Third.
BIOGRAPHY (top to bottom): Classmates Yearbook Archives; Ted Soqui/Corbis Sygma; Everett; Kevin Mazur/WireImage; Glenn Watson/20th Century FOX; Kobal Collection/Wireimage; Jeff Kravitz/FilmMagic; Darren Michaels/columbia Pictures; Eriko Sugita/Reuters/Landov