Following the indie films “The Last Supper” and “Feeling Minnesota”, Cameron Diaz then had a starring role in “Head Above Water”, a crime-comedy in which she played an unfaithful wife implicated in her ex-lover's murder.

She was scheduled to perform in the film “Mortal Kombat” but had to resign after breaking her hand while training for the role. Besides a starring part in the indie “A Life Less Ordinary”, Diaz returned to mainstream in 1997 with the romantic comedy “My Best Friend's Wedding”. In it, she starred opposite Julia Roberts, playing the wealthy fiancée of a sportswriter who is the long-time friend of Roberts' character. The film was a global box-office hit and is considered one of the best romantic comedy films of all time.

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. Directed by Peter Farrelly, who had previously worked on “Dumb and Dumber” in 1994 and “Kingpin” in 1996, most of the film was shot in Miami, Florida. The Big Pink Restaurant is where Healy meets with Sully and the Miami-Dade Cultural Center was the location for the architecture exhibit Mary and Healy attended together. The hair gel scene was filmed at the Cardozo Hotel, while Churchill's Pub was used as a strip club for a scene with Healy.

In 1998, Diaz also starred in the critically panned comedy “Very Bad Things” alongside Jon Favreau, Daniel Stern, Jeremy Piven, Christian Slater, Leland Orser, Kobe Tai and Jeanne Tripplehorn. The film was noted for having a very similar plot setup to “Stag”, a film which originally aired on HBO in June 1997.

In 1999, Diaz starred in Spike Jonze's directorial debut “Being John Malkovich”, portraying the pet-obsessed wife of an unemployed puppeteer who, through a portal, finds himself in the mind of actor John Malkovich. The film received widespread acclaim and was an arthouse success. The film was partly shot in New York and included the locations; Broadhurst Theatre at 235 West 44th Street and the apartment building at 620 Park Avenue. For her role, Diaz earned Best Supporting Actress nominations at the Golden Globe, BAFTA, and SAG Awards.

To close out the decade, her next film release was Oliver Stone's sports drama “Any Given Sunday”, where she played a young team owner who a veteran coach played by Al Pacino has fallen out of favour with.

Oliver Stone developed a script called “Monday Night” written by Jamie Williams, a former tight end for the Nebraska Cornhuskers and later the San Francisco 49ers, and Richard Weiner, a sports journalist. Stone separately acquired the spec script “On Any Given Sunday”, by John Logan. Stone later amalgamated a third screenplay, “Playing Hurt” by Daniel Pyne, into the project. The screenplay was also based in part on the 1994 book “You're Okay, It's Just a Bruise: A Doctor's Sideline Secrets” by Robert Huizenga. Huizenga was the intern doctor for the Los Angeles Raiders in their 1980s heyday, working under Dr. Robert T. Rosenfeld, who dismissed many players' injuries with the phrase, ‘You're okay, it's just a bruise’. James Woods' character was based on Rosenfeld, and his first diagnosis of Cap Rooney's career-threatening injury at the beginning of the film is ‘you're okay, it's just a bruise’. Huizenga left the Raiders in the early 1990s, disgusted at the way the medical advice was kept from players and Rosenfeld being allowed to continue treating them after several mishaps, one of which is closely mirrored in the film Shark's neck injury and risk of sudden death, based on the real-life Mike Harden case.

The film was shot in Miami, Florida and Irving, Texas. Miami's Orange Bowl stadium represents the home of the fictitious American football team, the Miami Sharks. When the team travelled to California, the stadium used was Pro Player Stadium, which is located in Miami Gardens. Texas Stadium is used for the home of the fictitious Dallas Knights.

Continues tomorrow with roles in “Charlie’s Angels”, “Vanilla Sky” and “Gangs of New York”.