As a follow-up to The Mask, Diaz chose a small, independent film called The Last Supper, which featured an ensemble cast that included Annabeth Gish, Ron Eldard, Jonathan Penner and Courtney B. Vance.

Her third feature was writer/director Steven Baigelman's offbeat love story Feeling Minnesota, in which she co-starred with Keanu Reeves and Vincent D'Onofrio. She went on to play a cold, manipulative New Yorker in Edward Burns' She's the One. She next starred opposite Harvey Keitel and Craig Sheffer in the thriller Head Above Water. In 1996, Diaz was named ShoWest's Female Star of Tomorrow by the National Association of Theatre Owners. In the summer of 1997, she co-starred with Julia Roberts, Dermot Mulroney and Rupert Everett in My Best Friend's Wedding, which became one of the ten top-grossing films of the year. Her performance earned her the Blockbuster Entertainment Award for Favorite Supporting Actress in a Comedy.

Diaz then starred opposite Ewan McGregor as a spoiled, unhappy rich girl who falls in love with a janitor who accidentally kidnaps her in Danny Boyle's A Life Less Ordinary.

For her performance in the title role of the romantic comedy There's Something About Mary, Diaz was honored with the New York Film Critics Circle Award as Best Actress. She also received a Golden Globe nomination, the American Comedy Award, the Netherlands' Best Actress Rembrandt Award, the Blockbuster Entertainment Award for Favorite Movie Performance and the MTV Movie Award for Best Female Performance.

Following Peter Berg's dark comedy Very Bad Things Diaz starred in the critically acclaimed Being John Malkovich opposite John Cusack, Catherine Keener and John Malkovich. Directed by Spike Jonze, her performance was nominated for a Golden Globe, the Screen Actors Guild Award and the British Academy Film Award.

In Oliver Stone's Any Given Sunday, Diaz co-starred with Al Pacino, Jamie Foxx, Dennis Quaid, LL Cool J, James Woods and Ann-Margaret. She appeared in The Invisible Circus, based on an acclaimed novel by Jennifer Egan and was seen on Showtime in Rodrigo Garcia's "Things You Can Tell Just By Looking At Her" with Glenn Close, Calista Flockhart, Amy Brenneman and Holly Hunter.

She provided the voice of the feisty Princess Fiona in Shrek with Mike Myers, Eddie Murphy and John Lithgow. The animated movie was one of the most successful films of 2001, setting box-office records and appearing on dozens of critics' lists of the year's best movies. She will reunite with the original voice cast for Shrek 2. The film will be released in summer, 2004.

Last year, she costarred in Martin Scorsese's Gangs of New York opposite Leonardo DiCaprio, Liam Neeson and Daniel Day-Lewis, and before that she co-starred in Cameron Crowe's Vanilla Sky with Tom Cruise, Penelope Cruz, Jason Lee and Kurt Russell. Her performance was nominated for a Golden Globe Award, an AFI Award and a SAG Award, and Diaz was chosen Best Supporting Actress by the Boston Society of Film Critics. She also co-starred in the comedy The Sweetest Thing with Christina Applegate and Selma Blair.