Movies Cameron Diaz through the years: From The Mask to EW's My Best Friend's Wedding reunion By EW Staff Published on February 7, 2019 12:00PM EST 01 of 28 The Mask (1994) Everett Collection Her first movie role, opposite Jim Carrey — and Jim Carrey's mask. 02 of 28 The Mask premiere (1994) Jim Smeal/WireImage At the Samuel Goldwyn Theater in Beverly Hills, Calif. 03 of 28 My Best Friend's Wedding (1997) Everett Collection If you ask us, Diaz could be crème brûlée or Jell-O. 04 of 28 My Best Friend's Wedding premiere (1997) Kevin Mazur/WireImage At Sony Theatres Lincoln Square in New York City. 05 of 28 My Best Friend's Wedding premiere (1997) Kevin Mazur Archive/WireImage Diaz cozies up to costar Julia Roberts. 06 of 28 There's Something About Mary (1998) Everett Collection The hairstyle she'll never live down. 07 of 28 There's Something About Mary premiere (1998) Steve Granitz/WireImage A young Diaz and a young Matt Dillon. 08 of 28 Any Given Sunday (1999) Everett Collection Diaz's character, football team owner Christina Pagniacci, dresses down Coach Tony D'Amato (Al Pacino). 09 of 28 Any Given Sunday premiere (1999) Steve Granitz/WireImage At the Mann Village Theatre in Los Angeles. 10 of 28 Charlie's Angels (2000) Everett Collection Diaz with Drew Barrymore and Lucy Liu. 11 of 28 Charlie's Angels premiere (2000) Jim Smeal/WireImage At the Mann Chinese Theatre in Los Angeles. 12 of 28 Vanilla Sky (2001) Everett Collection That's Tom Cruise, if you couldn't tell. 13 of 28 Vanilla Sky premiere (2001) Gregg DeGuire/WireImage At Grauman's Chinese Theatre in Los Angeles. 14 of 28 The Sweetest Thing (2002) Everett Collection Diaz raises a glass with Selma Blair and Christina Applegate. 15 of 28 The Sweetest Thing premiere (2002) Jim Spellman/WireImage The trio don all black on the red carpet. 16 of 28 Gangs of New York (2002) Miramax With Daniel Day-Lewis and his mustache. 17 of 28 Gangs of New York premiere (2002) Kevin Mazur/WireImage Diaz and Leonardo DiCaprio in — where else? — New York. 18 of 28 The Holiday (2006) Jude Law and Cameron Diaz in 'The Holiday'. Everett Collection What we would all give to have Jude Law look at us that way… 19 of 28 The Holiday premiere (2006) C. Uncle/FilmMagic Cam, Jude, and Kate Winslet in London. 20 of 28 What Happens in Vegas (2008) K.C. Bailey/Fox Diaz and Ashton Kutcher get (drunkenly) married. 21 of 28 What Happens in Vegas premiere (2008) Jun Sato/WireImage Ashton and Cameron take Tokyo. 22 of 28 Bad Teacher (2011) Everett Collection Good actress, bad teacher. 23 of 28 Bad Teacher premiere (2011) Steven Lawton/FilmMagic At the Colosseum at Caesars Palace in Las Vegas. 24 of 28 The Other Woman (2014) Barry Wetcher/Fox Diaz's character gets wooed by Nikolaj Coster-Waldau. 25 of 28 The Other Woman premiere (2014) Dave J Hogan/Getty Images …in London, baby. 26 of 28 Sex Tape (2014) Claire Folger/Columbia Pictures With costar Jason Segel. 27 of 28 Annie premiere (2014) Scott Roth/Invision/AP/REX/Shutterstock Diaz poses with the P.S. 153 chorus at the Ziegfeld Theatre in New York. 28 of 28 The My Best Friend's Wedding EW reunion Ruven Afanador for EW Diaz poses with her costars Rupert Everett, Dermot Mulroney, and Julia Roberts for the cover of our special rom-com-themed issue. Every day until Valentine’s Day, Entertainment Weekly is celebrating our special romantic-comedy-themed Untold Stories issue. Check out all our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram. Close