1Snapped in New York City
Mitchell Gerber//Getty Images Here, Diaz is posing for a photo in New York City in early-1994. However, Diaz was no stranger to the lens—she grew up in Long Beach, CA, and signed a modeling contract with Elite Model Management while in high school. She soon modeled in campaigns for brands such as Levi’s and Calvin Klein and landed a Seventeen magazine cover when she was still 17.
2With Jim Carrey at Cannes
Eric Robert//Getty Images The actress made her major film debut in 1994 when she snagged one of the lead roles in the Jim Carrey-lead film, The Mask. The two can be seen here at the Cannes Film Festival, promoting the film which would be releasing in the coming months.
3The Mask Los Angeles Premiere
Jim Smeal//Getty Images A few short months later, Diaz was snapped on the red carpet for the first of her many Hollywood premieres, wearing a gorgeous magenta gown paired with translucent heels. The movie was nominated for one Oscar and is still considered a cult classic today.
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4Chatting on The Tonight Show with Jay Leno
NBC//Getty Images That same year, Diaz appeared on The Tonight Show with Jay Leno to discuss her recent projects. The guest she's sitting next to is Richard Lewis, an actor and stand-up comedian known for Curb Your Enthusiasm and Anything But Love.
51995 Toyota Grand Prix Celebrity Race
Mitchell Gerber//Getty Images In 1995, the young actress put on her racing gear and hopped into one of the cars at the Toyota Grand Prix. She was a part of the Celebrity Car Race, which included other Hollywood icons like Matt LeBlanc from Friends and Mark-Paul Gosselaar from Saved by the Bell. The big celebrity winner that year was Alfonso Ribeiro from The Fresh Prince of Bel-Air.
6In Costume Filming She’s the One
Ron Galella//Getty Images In October of that same year, she filmed She’s the One, a romantic comedy that Edward Burns wrote, directed, and starred in as her character Heather's ex-fiancé.
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7Posing Expertly for the Camera
mikel roberts//Getty Images In 1996, she returned to her modeling roots and posed for photographer Mikel Roberts wearing a strapless bathing suit and a colorful swim cap. She had a huge year in 1996 along with She's The One, also starring in Feeling Minnesota alongside Keanu Reeves and Head Above Water with Harvey Keitel.
8My Best Friend’s Wedding Premiere Party
Ron Galella, Ltd.//Getty Images One year later, Diaz stopped by the premiere party for her classic romantic comedy My Best Friend’s Wedding, where she played the fiancé of star Julia Roberts' love interest. The event was held at The Plaza Hotel and Diaz was glowing even in a simple gown.
9There’s Something About Mary Los Angeles Premiere
Steve Granitz//Getty Images 1998 was a busy year for Diaz. She appeared in Fear and Loathing in Las Vegas and acted in Very Bad Things just to start. It was also the year she released one of her biggest movies, the romantic comedy There’s Something About Mary, which earned her a nomination for a Golden Globe award. Here, she can be seen at the movie’s red carpet premiere with her co-star (and then-boyfriend), Matt Dillon.
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10Being John Malkovich New York City Premiere
Robin Platzer/Twin Images//Getty Images Diaz donned dark tresses at the NYC premiere of Being John Malkovich. The twenty-something-year-old star plays the main character’s wife, Lotte Schwartz, in the creative film that was helmed by Her director Spike Jonze.
11New York Screening of Charlie’s Angels
Steve.Granitz//Getty Images Remember how big the 2000 remake of Charlie’s Angels was when it came out? Here, Diaz poses with her two co-stars, Lucy Liu and Drew Barrymore, before the movie’s NYC screening. The three reunited over 20 years later on an episode of Drew Barrymore’s talk show. “We’ve been through everything together,” Barrymore said during the 2022 sit-down interview.
12Rocking the Vanilla Sky Premiere
Jeff Kravitz//Getty Images In 2001, Diaz attended Vanilla Sky’s red carpet premiere wearing an eye-catching patterned hat, chandelier earrings, and a black denim jacket. She starred in the early-2000s thriller flick, joining other big names, including Tom Cruise, Penelope Cruz, and Kurt Russell.
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13The Sweetest Thing New York City Premiere
Evan Agostini//Getty Images Here, Diaz poses with co-stars Christina Applegate and Selma Blair during the NYC premiere of their film, The Sweetest Thing. It's a solid comedy flick that was nominated for multiple Teen Choice Awards that year.
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