People.com Celebrity Cameron Diaz's Most Iconic Photos, on Her Path from Movie Star to Motherhood The actress, who turns 48 on Aug. 30, has been a trendsetter and trailblazer since her 1994 debut in The Mask. Look back at some of her most major style moments and career highlights — as well as her recent focus on her happy home life with husband Benji Madden and their daughter Raddix By People Staff Published on August 30, 2021 08:00 AM Share Tweet Pin Email 01 of 24 Jim Smeal/Ron Galella Collection via Getty Images Cameron Diaz, 22, was the epitome of "fresh faced" when she attended a promo event for her breakout film, The Mask, in 1994. 02 of 24 David Keeler/Getty Images Diaz and costar Jim Carrey had the bright idea at the film's Hollywood premiere. (This whole gallery of photos of Diaz from that time is all the frosted brown lipstick inspiration you need.) 03 of 24 Jim Smeal/Ron Galella Collection via Getty Her appearance at the 1995 Oscars also marked the appearance of her seriously iconic blunt bob. 04 of 24 Kevin Mazur/WireImage This is the 1995 MTV Movie Awards, which you have definitely already guessed from looking at it. 05 of 24 Ron Galella, Ltd./Ron Galella Collection via Getty Images Diaz and Matt Dillon were one of the "It" couples of the '90s; in this 1996 shot, they're hitting all the major style notes from loose chinos to mock turtlenecks. 06 of 24 Kevin Mazur Archive/WireImage No word on whether Julia Roberts and Diaz fought in the bathroom at the 1997 premiere of My Best Friend's Wedding. 07 of 24 The LIFE Picture Collection/Shutterstock Things took a darker turn — literally and follicularly — for the 1999 premiere of Being John Malkovich. 08 of 24 Jim Smeal/Ron Galella Collection via Getty Images We say a little prayer for cute reunion moments between Diaz and Roberts any time they're on a red carpet — like the 2000 Golden Globes. 09 of 24 Gregg DeGuire/WireImage Perhaps no star has loved a formal hat moment more than Diaz (wearing one of her signature chapeaus at the 2001 premiere of Vanilla Sky). 10 of 24 Jeff Kravitz/FilmMagic You might not recognize Diaz and Shrek costar Mike Myers (in 2001) out of their ogre suits. 11 of 24 Scott Gries/Getty Images If the phrase "the cast of The Sweetest Thing on TRL in 2002" doesn't give you intense nostalgia, we don't what will. (Diaz is seen with costars Selma Blair and Christina Applegate.) 12 of 24 Frank Micelotta/Getty Diaz calls the look she wore to the 2002 Oscars her favorite she's ever worn — and it came together last minute. Makeup artist Gucci Westman called in a favor to get the Emanuel Ungaro gown when she needed it at the last minute, and she tossed on a $20 turquoise bracelet to finish it off. 13 of 24 The actress made a memorable Cannes debut in 2002 for Gangs of New York. 14 of 24 Jim Smeal/Ron Galella Collection via Getty Images At the 2003 Charlie's Angels: Full Throttle premiere, Diaz and costars Lucy Liu and Drew Barrymore decided to go positively angelic in coordinating white looks. (And Diaz ditched her shoes entirely after a snapped heel incident.) 15 of 24 Frank Micelotta/Getty We assume this photo from the 2003 Kids' Choice Awards is framed on all of their mantels. 16 of 24 Lisa Blumenfeld/Getty Images Cameron Diaz and Justin Timberlake dated from 2003 to 2007, after meeting at the Kids' Choice Awards the year before. 17 of 24 KMazur/WireImage Fun fact: Diaz and her future husband Benji Madden (pictured with brother and Good Charlotte bandmate Joel, Lance Bass and Beverley Mitchell) first crossed paths at an 'NSYNC-hosted charity basketball tournament in 2004, where Diaz was there on team Timberlake. 18 of 24 Snap Stills/REX Shutterstock Gratuitous The Holiday content time. 19 of 24 Brian ZAK/Gamma-Rapho via Getty Images The star has had many memorable trips up the Met Gala steps, but this magenta Christian Dior Couture with turquoise Fred Leighton jewelry (from 2007) is a perpetual favorite. 20 of 24 Alberto E. Rodriguez/Getty Images The star glittered in a golden Oscar de la Renta gown at the 2010 Oscars. 21 of 24 Theo Wargo/NBC/Getty Images The star dropped by (so to speak) pal Jimmy Fallon's talk show in 2014. 22 of 24 Cameron Diaz Instagram 2014's Annie would be her last film to date. In recent years, Diaz has been open about her pivot away from acting, saying she "wanted to make my life manageable." That means taking on new projects like wellness books and a natural wine brand, Avaline. 23 of 24 Benji Madden and Cameron Diaz. Donato Sardella/Getty She's also been married since Jan. 2015 to Benji Madden (which yes, makes her sisters-in-law with Nicole Richie, married to his brother Joel). They welcomed daughter Raddix in Dec. 2019. 24 of 24 Noel Vasquez/GC Images "Now I'm here and this is the most fulfilling thing that I've ever done in my life," Diaz has said about her newfound focus. "[To] have a family and be married and have our little nucleus of a family. It's just completely the best thing."