Cameron Diaz through the years: From The Mask to EW's My Best Friend's Wedding reunion

01 of 28

The Mask (1994)

THE MASK (US1994) JIM CARREY, CAMERON DIAZ
Everett Collection

Her first movie role, opposite Jim Carrey — and Jim Carrey's mask.

02 of 28

The Mask premiere (1994)

"The Mask" Los Angeles Premiere
Jim Smeal/WireImage

At the Samuel Goldwyn Theater in Beverly Hills, Calif.

03 of 28

My Best Friend's Wedding (1997)

MY BEST FRIEND'S WEDDING, Julia Roberts, Cameron Diaz, 1997. © TriStar Pictures/ Courtesy: Everett C
Everett Collection

If you ask us, Diaz could be crème brûlée or Jell-O.

04 of 28

My Best Friend's Wedding premiere (1997)

"My Best Friend's Wedding" New York City Premiere Party
Kevin Mazur/WireImage

At Sony Theatres Lincoln Square in New York City.

05 of 28

My Best Friend's Wedding premiere (1997)

"My Best Friend's Wedding" New York City Premiere Party
Kevin Mazur Archive/WireImage

Diaz cozies up to costar Julia Roberts.

06 of 28

There's Something About Mary (1998)

THERE'S SOMETHING ABOUT MARY, Cameron Diaz, 1998. TM and Copyright ©20th Century Fox Film Corp. All
Everett Collection

The hairstyle she'll never live down.

07 of 28

There's Something About Mary premiere (1998)

"There's Something About Mary" Los Angeles Premiere
Steve Granitz/WireImage

A young Diaz and a young Matt Dillon.

08 of 28

Any Given Sunday (1999)

ANY GIVEN SUNDAY, Cameron Diaz, Al Pacino, 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)

"Any Given Sunday" Los Angeles Premiere
Steve Granitz/WireImage

At the Mann Village Theatre in Los Angeles.

10 of 28

Charlie's Angels (2000)

CHARLIE'S ANGELS, Drew Barrymore, Cameron Diaz, Lucy Liu, 2000, (c) Columbia/courtesy Everett Collec
Everett Collection

Diaz with Drew Barrymore and Lucy Liu.

11 of 28

Charlie's Angels premiere (2000)

"Charlie's Angels" Los Angeles Premiere
Jim Smeal/WireImage

At the Mann Chinese Theatre in Los Angeles.

12 of 28

Vanilla Sky (2001)

VANILLA SKY, Tom Cruise, Cameron Diaz, 2001
Everett Collection

That's Tom Cruise, if you couldn't tell.

13 of 28

Vanilla Sky premiere (2001)

"Vanilla Sky" Los Angeles Premiere
Gregg DeGuire/WireImage

At Grauman's Chinese Theatre in Los Angeles.

14 of 28

The Sweetest Thing (2002)

MSDSWTH EC004
Everett Collection

Diaz raises a glass with Selma Blair and Christina Applegate.

15 of 28

The Sweetest Thing premiere (2002)

"The Sweetest Thing" - Premiere
Jim Spellman/WireImage

The trio don all black on the red carpet.

16 of 28

Gangs of New York (2002)

"Gangs of New York"
Miramax

With Daniel Day-Lewis and his mustache.

17 of 28

Gangs of New York premiere (2002)

"Gangs of New York" World Premiere
Kevin Mazur/WireImage

Diaz and Leonardo DiCaprio in — where else? — New York.

18 of 28

The Holiday (2006)

THE HOLIDAY, Jude Law, Cameron Diaz, 2006. ©Columbia Pictures/courtesy Everett Collection
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)

"The Holiday" - London Premiere - Outside Arrivals
C. Uncle/FilmMagic

Cam, Jude, and Kate Winslet in London.

20 of 28

What Happens in Vegas (2008)

WHAT HAPPENS IN VEGAS
K.C. Bailey/Fox

Diaz and Ashton Kutcher get (drunkenly) married.

21 of 28

What Happens in Vegas premiere (2008)

"What Happens In Vegas" Japan Premiere
Jun Sato/WireImage

Ashton and Cameron take Tokyo.

22 of 28

Bad Teacher (2011)

BAD TEACHER, Cameron Diaz, 2011. Ph: Gemma LaMana/©Columbia PictureS/Courtesy Everett Collection
Everett Collection

Good actress, bad teacher.

23 of 28

Bad Teacher premiere (2011)

2011 CinemaCon - Day 3
Steven Lawton/FilmMagic

At the Colosseum at Caesars Palace in Las Vegas.

24 of 28

The Other Woman (2014)

THE OTHER WOMAN
Barry Wetcher/Fox

Diaz's character gets wooed by Nikolaj Coster-Waldau.

25 of 28

The Other Woman premiere (2014)

"The Other Woman" - UK Gala Premiere - Inside Arrivals
Dave J Hogan/Getty Images

…in London, baby.

26 of 28

Sex Tape (2014)

Cameron Diaz;Jason Segel
Claire Folger/Columbia Pictures

With costar Jason Segel.

27 of 28

Annie premiere (2014)

NY Premiere "Annie" - Red Carpet, New York, USA
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

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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.

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