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In 2013, Diaz was named the highest-paid actress over 40 in Hollywood. Her mother, Billie (née Early; born August 11, 1950), was an import/export agent, and her father, Emilio (Queso) Diaz (July 3, 1949 – April 15, 2008), worked for the California oil company Unocal as a foreman. She began her career as a fashion model at the age of 16 and did contract work with a modeling agency, Elite Model Management.
For the next year, she worked all over the world on contracts for companies including Calvin Klein and Levi's.
The film was a global box-office hit In 1998, Diaz starred in There's Something About Mary, as the titular role of a woman living in Miami having several men vying for her affections.
SPLICEDwire found Diaz to be "in a tough spot as Mary [but] strikes an amazingly nimble balance between her character's endearing preciousness and the movie's twisted humor", and Austin Chronicle remarked: "As the Mary at the center of it all, Diaz certainly exudes that irresistible “something” expressed in the title.
For her role, Diaz earned Best Supporting Actress nominations at the Golden Globe, BAFTA, and SAG Awards.
Her next film release in 1999 was Oliver Stone's sports drama Any Given Sunday, where she played a young team owner who a veteran coach (Al Pacino) has fallen out of favor with.
A wide critical response and commercial success greeted Vanilla Sky upon its release; Los Angeles Times called her "compelling as the embodiment of crazed sensuality" and The New York Times said she gives a "ferociously emotional" performance.