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

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Cameron Diaz
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.

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Cameron Diaz
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.)

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Cameron Diaz
Jim Smeal/Ron Galella Collection via Getty

Her appearance at the 1995 Oscars also marked the appearance of her seriously iconic blunt bob.

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Cameron Diaz
Kevin Mazur/WireImage

This is the 1995 MTV Movie Awards, which you have definitely already guessed from looking at it.

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Cameron Diaz
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.

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Cameron Diaz
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.

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Cameron Diaz
The LIFE Picture Collection/Shutterstock

Things took a darker turn — literally and follicularly — for the 1999 premiere of Being John Malkovich.

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Cameron Diaz
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.

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Cameron Diaz
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).

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Cameron Diaz
Jeff Kravitz/FilmMagic

You might not recognize Diaz and Shrek costar Mike Myers (in 2001) out of their ogre suits.

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Cameron Diaz
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.)

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Cameron Diaz
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.

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Cameron Diaz

The actress made a memorable Cannes debut in 2002 for Gangs of New York.

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Cameron Diaz
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.)

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Cameron Diaz
Frank Micelotta/Getty

We assume this photo from the 2003 Kids' Choice Awards is framed on all of their mantels.

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Cameron Diaz; Justin Timberlake
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Cameron Diaz and Justin Timberlake dated from 2003 to 2007, after meeting at the Kids' Choice Awards the year before.

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Cameron Diaz

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.

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Snap Stills/REX Shutterstock

Gratuitous The Holiday content time.

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Cameron Diaz
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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.

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Cameron Diaz
Alberto E. Rodriguez/Getty Images

The star glittered in a golden Oscar de la Renta gown at the 2010 Oscars.

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Cameron Diaz
Theo Wargo/NBC/Getty Images

The star dropped by (so to speak) pal Jimmy Fallon's talk show in 2014.

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Cameron Diaz Instagram
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.

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Benji Madden Cameron Diaz
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.

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Cameron Diaz
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."

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