[1] Her output of romantic comedies in the late 1990s and early 2000s established her as a prominent sex symbol and one of Hollywood's most bankable stars, and in 2013 she was named the highest-paid actress over 40.

Diaz received praise for her supporting roles in Cameron Crowe's Vanilla Sky (2001) and Martin Scorsese's Gangs of New York (2002) and had greater commercial success in the action comedy Charlie's Angels (2000) and its 2003 sequel, as well as for voicing Princess Fiona in the Shrek franchise (2001–present).

[19][20][21] At the age of 21, Diaz auditioned for The Mask, playing a jazz singer named Tina Carlyle,[22] based on the recommendation of an agent for Elite, who met the film's producers while they were searching for the lead actress.

[26] Diaz subsequently starred in the independent black comedy The Last Supper (1995), playing one of several liberal graduate students who invite a group of extremist conservatives to a dinner in an attempt to murder them.

[27] Roger Ebert deemed the film "a brave effort in a timid time, a Swiftian attempt to slap us all in the face and get us to admit that our own freedoms depend precisely on those of our neighbors, our opponents and, yes, our enemies.

"[28] She then had a lead role as an ex-stripper in the dramatic comedy Feeling Minnesota (1996), in which she co-starred opposite Keanu Reeves, Vincent D'Onofrio, and Courtney Love.

[29] Emanuel Levy of Variety noted: "Sadly, with the notable exception of the attractive Diaz, who's well cast as the sexual aggressor and romantic manipulator, there are no exciting performances in the film.

"[29] The same year, she was cast opposite Jennifer Aniston in the Edward Burns-directed comedy She's the One (1996),[30] followed by a starring role in Head Above Water (1996), a crime-comedy in which she played an unfaithful wife implicated in her ex-lover's murder.

[41] For her role, Diaz earned Best Supporting Actress nominations at the Golden Globe, BAFTA, and SAG Awards, however, she was snubbed for the Oscar, which was met with backlash.

Her next film release in 1999 was Oliver Stone's sports drama Any Given Sunday (1999), in which veteran coach Tony D’Amato (Al Pacino) has fallen out of favor with her character Christina Pagniacci, the young woman who owns the team.

[43] In 2001, Diaz starred in the Sundance-premiered independent drama The Invisible Circus, as a young woman who commits suicide in Europe in the 1970s, and next in the year, she appeared in Vanilla Sky, as the former lover of a self-indulgent and vain publishing magnate (Tom Cruise).

[47][48] In 2002, Diaz headlined the romantic comedy The Sweetest Thing, playing a single woman educating herself on wooing the opposite sex when she finally meets the man of her dreams.

[50][51] A. O. Scott of The New York Times, agreeing with other top critics on co-star Daniel Day-Lewis's presence overshadowing Diaz and DiCaprio,[52][53] felt that the actress "ends up with no outlet for her spitfire energies, since her character is more a structural necessity — the linchpin of male jealousy — than a fully imagined person.

Diaz received substantial defamation damages from suing American Media Incorporated, after the National Enquirer posted an article and pictures with the headline "Cameron Caught Cheating" on their website in May 2005.

The magazine apologized to Diaz, Timberlake, Nickerson and his wife for the distress caused and said the story was untrue and the picture showed no more than a goodbye hug between friends.

The film received generally positive reviews from critics,[57] and Diaz garnered acclaim for her performance of a dyslectic wild child engaged in a love-hate struggle with her plain, sensible sister (Collette), with USA Today calling it "her best work" at the time.

[58] She followed In Her Shoes with a role in Nancy Meyers' romantic comedy The Holiday (2006), also starring Kate Winslet, Jude Law, and Jack Black.

[62] Diaz earned an estimated US$50 million during the period of a year ending June 2008, for her roles in the Shrek sequel and her next film What Happens in Vegas opposite Ashton Kutcher.

[63][64] A romantic comedy by Tom Vaughan, Diaz and Kutcher portrayed two strangers who awaken together to discover they have gotten married following a night in which they won a huge jackpot after playing the other's quarter.

Directed by Michel Gondry, Diaz starred alongside Seth Rogen, Jay Chou, and Christoph Waltz in the superhero action comedy film.

Released to mixed to negative reviews from critics, who called it an "overblown, interminable and unfunny update",[79] the film ended its theatrical run on April 21, 2011, with a worldwide gross total of US$228 million.

Again, it received mostly negative reviews from critics who felt that "in spite of a promising concept and a charmingly brazen performance from Diaz, Bad Teacher is never as funny as it should be.

[88] Diaz also voiced Sigmund Freud in A Liar's Autobiography (2012), a British animated comedy film that is a (deliberately) completely inaccurate portrayal[89] of the life of Monty Python alumnus Graham Chapman.

Diaz's only film project of 2013 was Ridley Scott's The Counselor, co-starring Michael Fassbender, Javier Bardem, Penélope Cruz, and Brad Pitt.

In the thriller about greed, death, the primal instincts of humans and their consequences, Diaz plays a pathological liar and a sociopath, an immigrant who is now living the high-life after escaping a sordid past as an exotic dancer.

[99] Upon its December premiere, Annie made US$133 million worldwide, with Diaz's performance garnering polarized reviews; critics praising her effort, but ultimately calling it too "vampy",[100] as well as "strident and obnoxious".

[102] Diaz decided to take a break from acting following the release of Annie, stating in July 2017 that she became tired of traveling for filming,[103] and confirmed her retirement the following March.

[113] In 2022, she appeared as a guest judge in the season opener episode of RuPaul's Drag Race All Stars 7, and stated she was a huge fan of the show.

[124][125] The couple had been introduced ten months earlier by her close friend Nicole Richie who is married to Madden's twin brother Joel.

[131] Known for her environmental activism, Diaz was an early adopter of the Toyota Prius hybrid and worked to promote Al Gore's Live Earth campaign, raising awareness of climate change.