Later that year, she turned in a brazen performance as the glamorous, hard-nosed new owner of a professional football team in Oliver Stone’s Any Given Sunday, costarring Al Pacino and Dennis Quaid.

Despite her undeniable box office appeal, Diaz continued to appear in relatively low-budget independent films—including the black comedy Very Bad Things (1998), Malkovich, and the ensemble film Things You Can Tell Just by Looking at Her (2000), which aired on Showtime cable television in 2001 and costarred Glenn Close, Holly Hunter, and Calista Flockhart—as well as more mainstream projects. In the fall of 2000, she starred alongside Drew Barrymore and Lucy Liu as one of the three female detectives at the heart of the hit big-screen remake of Aaron Spelling’s campy 1970s television show, Charlie’s Angels.

In early 2001, Diaz appeared as a free spirited older sister in The Invisible Circus. She also provided the voice for the spirited Princess Fiona in that summer's animated hit Shrek, also featuring the voices of Mike Myers and Eddie Murphy. Her upcoming projects include Martin Scorsese’s Gangs of New York, costarring Leonardo DiCaprio, and Cameron Crowe’s Vanilla Sky, costarring Tom Cruise (both 2001).

Diaz’s five-year relationship with video producer Carlos de La Torre ended in 1995. She dated her There’s Something About Mary costar Matt Dillon from 1996 to 1998. In 1999, she began dating the actor Jared Leto.