The Mask (1994)
![THE MASK (US1994) JIM CARREY, CAMERON DIAZ](https://ew.com/thmb/C3EIz0CmDC_inYtgvu6iljYJVzc=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/htra213_vv232-2000-6b061619563b459bb112ab5d370e6d52.jpg)
Her first movie role, opposite Jim Carrey — and Jim Carrey's mask.
The Mask premiere (1994)
!["The Mask" Los Angeles Premiere](https://ew.com/thmb/7bs-U3_eUqUKrpMkoXYBwLHXWfg=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-75498333-2000-059a9e2812fd4c6d9fcd247cdf200e7b.jpg)
At the Samuel Goldwyn Theater in Beverly Hills, Calif.
My Best Friend's Wedding (1997)
![MY BEST FRIEND'S WEDDING, Julia Roberts, Cameron Diaz, 1997. © TriStar Pictures/ Courtesy: Everett C](https://ew.com/thmb/O8v9aocj8G8ch6t8Wdi8DpQ04CE=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/msdmybe_ec008-2000-b1d1238f10ed4a079da44f9be0742fd8.jpg)
If you ask us, Diaz could be crème brûlée or Jell-O.
My Best Friend's Wedding premiere (1997)
!["My Best Friend's Wedding" New York City Premiere Party](https://ew.com/thmb/53X6V6KtqxOeZNz8KzlOcxke2gA=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-88627701-2000-812567cf953c470ea41e2bf9f136610f.jpg)
At Sony Theatres Lincoln Square in New York City.
My Best Friend's Wedding premiere (1997)
!["My Best Friend's Wedding" New York City Premiere Party](https://ew.com/thmb/KlaAG67qsnTGw-BMjMfV2Uh33CA=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-76135697-2000-e89b14b15a374c119a71ea84e1fdbb95.jpg)
Diaz cozies up to costar Julia Roberts.
There's Something About Mary (1998)
![THERE'S SOMETHING ABOUT MARY, Cameron Diaz, 1998. TM and Copyright ©20th Century Fox Film Corp. All](https://ew.com/thmb/bapokSgACxhqMjitt4FJnmbF6WY=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/msdthso_fe005-2000-bb30b709cadc4582a5c4040b4066f9ba.jpg)
The hairstyle she'll never live down.
There's Something About Mary premiere (1998)
!["There's Something About Mary" Los Angeles Premiere](https://ew.com/thmb/jo1F0B9FmYl_o_fwEF0UdM6STRg=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-75482790-2000-b7eacb7e5cd64b929634b9895231a539.jpg)
A young Diaz and a young Matt Dillon.
Any Given Sunday (1999)
![ANY GIVEN SUNDAY, Cameron Diaz, Al Pacino, 1999](https://ew.com/thmb/ja5Cp-loVVS-wQW53dabNd7rc2M=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/msdangi_ec004-2000-8368290ede7c40eb8ab5c851d4f32848.jpg)
Diaz's character, football team owner Christina Pagniacci, dresses down Coach Tony D'Amato (Al Pacino).
Any Given Sunday premiere (1999)
!["Any Given Sunday" Los Angeles Premiere](https://ew.com/thmb/_6xk8BhyMHwy1YM73C8LZOl_Uk4=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-104601184-2000-93a3ddd1ab7c4a9e91a439ecce69f9b2.jpg)
At the Mann Village Theatre in Los Angeles.
Charlie's Angels (2000)
![CHARLIE'S ANGELS, Drew Barrymore, Cameron Diaz, Lucy Liu, 2000, (c) Columbia/courtesy Everett Collec](https://ew.com/thmb/SihrQuq5hghIbGmW62RdBJYAB5E=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/mcdchan_ec272_h-2000-2ccdf42ca170400aafe14364f775ae3a.jpg)
Diaz with Drew Barrymore and Lucy Liu.
Charlie's Angels premiere (2000)
!["Charlie's Angels" Los Angeles Premiere](https://ew.com/thmb/dl_GwlQYoEXr9lWtJ3rLPVqfZ1s=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-115371208-2000-3c228db1a4984d9abb7317871709b0cc.jpg)
At the Mann Chinese Theatre in Los Angeles.
Vanilla Sky (2001)
![VANILLA SKY, Tom Cruise, Cameron Diaz, 2001](https://ew.com/thmb/Jk8E5XvSRGEwB1JZ8OixlPt0eQI=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/msdvask_ec003-2000-a84104b758fe40e4ab6a517699369d48.jpg)
That's Tom Cruise, if you couldn't tell.
Vanilla Sky premiere (2001)
!["Vanilla Sky" Los Angeles Premiere](https://ew.com/thmb/6iWZ3jOGi4pbMl5wPGNUywuLj_4=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-75503180-2000-14677c6a175e469fa0cef2d40424f5ae.jpg)
At Grauman's Chinese Theatre in Los Angeles.
The Sweetest Thing (2002)
![MSDSWTH EC004](https://ew.com/thmb/SWbqJ4X-sEVhBuJcH-gLY3fRI_I=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/ct414_h-2000-22f585fe97524870a5886e259ae79907.jpg)
Diaz raises a glass with Selma Blair and Christina Applegate.
The Sweetest Thing premiere (2002)
!["The Sweetest Thing" - Premiere](https://ew.com/thmb/8au2HODfU19tTmiU8Nu-ni5JfJU=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-112343132-2000-3373a533f4f8409bba3a6354dd234fb3.jpg)
The trio don all black on the red carpet.
Gangs of New York (2002)
!["Gangs of New York"](https://ew.com/thmb/uMm_jHgGt2Xm8ivLYLMFNRlf9xc=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gangs-of-new-york-11-2000-d9fcb4ef23c44272a79ad64c09088ac6.jpg)
With Daniel Day-Lewis and his mustache.
Gangs of New York premiere (2002)
!["Gangs of New York" World Premiere](https://ew.com/thmb/LMIrOtyQEY0jPO0NKxzHfy1JA9g=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-105029163-2000-dec3311f0e5b4dd4a70306b365b68dbc.jpg)
Diaz and Leonardo DiCaprio in — where else? — New York.
The Holiday (2006)
![THE HOLIDAY, Jude Law, Cameron Diaz, 2006. ©Columbia Pictures/courtesy Everett Collection](https://ew.com/thmb/KgS3s2yfcKsaHlojde1uuDlJeXM=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/MCDHOLI_EC015-2000-5d538cde8f5b4de6b4f59c9d1e52c956.jpg)
What we would all give to have Jude Law look at us that way…
The Holiday premiere (2006)
!["The Holiday" - London Premiere - Outside Arrivals](https://ew.com/thmb/OFGYWQC5E1UoOw8uKvTYw5wlA0E=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-111573496-2000-9de9b6224ac84fceb7bebd80c13bdbcb.jpg)
Cam, Jude, and Kate Winslet in London.
What Happens in Vegas (2008)
![WHAT HAPPENS IN VEGAS](https://ew.com/thmb/W5iZpaamUimQgMH_i7x_2M09kaA=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/vks-145-2000-65839ad02dda4f33bfbca11b7542deee.jpg)
Diaz and Ashton Kutcher get (drunkenly) married.
What Happens in Vegas premiere (2008)
!["What Happens In Vegas" Japan Premiere](https://ew.com/thmb/ATkvpMsdE82L3HQnMdF9rTz81c8=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-82192379-2000-b2115beac29e462186a500770ce18578.jpg)
Ashton and Cameron take Tokyo.
Bad Teacher (2011)
![BAD TEACHER, Cameron Diaz, 2011. Ph: Gemma LaMana/©Columbia PictureS/Courtesy Everett Collection](https://ew.com/thmb/_QLPjvyCCD_04zeAE61FcP1833Q=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/MCDBATE_EC032-2000-e763d25d0954415d96181124c6212e20.jpg)
Good actress, bad teacher.
Bad Teacher premiere (2011)
![2011 CinemaCon - Day 3](https://ew.com/thmb/tGWUujgM2Inb4J3xVSAQmqUI4Gk=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-111211950-2000-156c431c853f469c81c472a918fd5e1f.jpg)
At the Colosseum at Caesars Palace in Las Vegas.
The Other Woman (2014)
![THE OTHER WOMAN](https://ew.com/thmb/_j9aX3lrXPV-maAy3CLykcXTBPs=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/df-12266r_rgb-2000-3194a0a320da41d5a34271d8c829a8c7.jpg)
Diaz's character gets wooed by Nikolaj Coster-Waldau.
The Other Woman premiere (2014)
!["The Other Woman" - UK Gala Premiere - Inside Arrivals](https://ew.com/thmb/tEWpZEIJ5wAEp5la6xiC-in1XeM=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/gettyimages-482011429-2000-ba1c91405c0c432894979f9811949613.jpg)
…in London, baby.
Sex Tape (2014)
![Cameron Diaz;Jason Segel](https://ew.com/thmb/SOg_T_RYfPm9tjzZtqpgPegs3II=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/df-03159_r-2000-2c2935e4a00a43b6b9639d7d1b42fabb.jpg)
With costar Jason Segel.
Annie premiere (2014)
![NY Premiere "Annie" - Red Carpet, New York, USA](https://ew.com/thmb/ge-u7B_CktT6GPYVIVS3D5-JxfU=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/shutterstock_editorial_9082802am_huge-2000-b02f871ebf4e4c149b039a30449f43c3.jpg)
Diaz poses with the P.S. 153 chorus at the Ziegfeld Theatre in New York.
The My Best Friend's Wedding EW reunion
![EW1549_mbfw_37832738289321](https://ew.com/thmb/pkzVQQtBqFKARw11xqcDGEPGIRo=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/ew1549_mbfw_37832738289321-2000-3ff881fc1f594e729a41ffbc3c1f2bb9.jpg)
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.