Cameron Diaz then cooperated with Oliver Stone in his 1999 film Any Given Sunday. She portrayed the owner of the Miami Sharks, who inherits the team from her father. Diaz made a radical switch in this picture, from her previous girl-next-door image to a tough team owner.

It was her 2000 movie Charlie's Angels that captured the bulk of attention. The action-comedy is based on the 1970s TV series of the same name. Cameron Diaz starred with Drew Barrymore and Lucy Liu as three women working for a private investigating agency. The film won enthusiastic response from theater-goers for its stunning action scenes and model-like lead roles with fast-changing fancy dress.

Cameron Diaz went on to star in a number of films. In 2001 she was nominated for Best Supporting Actress at the Golden Globes, and the SAG Awards for Vanilla Sky, playing opposite Tom Cruise. In 2003 Diaz received another Golden Globe nomination for Martin Scorsese's epic Gangs of New York, and became the third actress to earn 20 million for a role, after Julia Roberts and Reese Witherspoon.

Diaz also appeared in The Holiday, and What Happens in Vegas. In 2007, People Magazine ranked her as the Best Dressed Female Celebrity.