If Meg Ryan’s gloriously cozy ’90s oeuvre—When Harry Met Sally, Sleepless in Seattle, You’ve Got Mail—is the rom-com equivalent of a steaming hot cup of cocoa, and Julia Roberts’s—Pretty Woman, Notting Hill, Runaway Bride—is more akin to a large glass of merlot, Cameron Diaz’s resembles a tall, fizzy flute of Champagne: impossibly glamorous, heady, and just a whole lot of fun. She’s been the dressed-to-kill bombshell, the wholesome girl next door, and everything in between.
Now, after a decade-long hiatus from acting, Diaz has made her triumphant return: In the new Netflix thriller Back in Action, she and her longtime friend, Jamie Foxx, play a pair of married 50-something former CIA operatives whose secret identities are exposed, drawing them back into the perilous world of espionage. Navigating high-octane car chases and fist fights alongside goofing around with her partner and jointly parenting two young kids, she’s as charming as ever—her comic timing just as precise and her star power wholly evident.
To celebrate its release, we shortlist five of Cameron Diaz’s most memorable rom-com performances from the ’90s and aughts—all of which are well worth a rewatch.
The Mask (1994)
Wind the clock back by just over three decades, and you’ll arrive at Diaz’s scintillating screen debut. Aged 21, she played the irresistible Tina Carlyle—an arch-eyebrowed, glossy-haired femme fatale (though, ultimately, one with a heart of gold) who has everyone, including Jim Carrey’s titular fleet-footed menace, wrapped around her little finger in Chuck Russell’s madcap romp. From that devastating entrance shortly after the opening credits to her breathy musical number, it marked one hell of a breakout moment.
My Best Friend’s Wedding (1997)
Then, in P. J. Hogan’s ’90s classic, she’s the anti-Tina Carlyle: Kimmy Wallace, the wide-eyed, kind-hearted, twinset and pearls-wearing Pollyanna who wins the heart of Dermot Mulroney’s dashing sports writer and acts as the sugary sweet foil to Julia Roberts’s whip-smart, no-nonsense food critic. But underestimate her at your peril: a reckless driver who is horrifyingly bad at karaoke, she defies our expectations at every turn, and most dramatically at the end, when she confronts our leading lady with a ferociousness that no one could have seen coming. A delight.
There’s Something About Mary (1998)
As the utterly luminous Mary Jensen—a Princeton graduate with a successful orthopedic practice, who loves to golf and has a deliciously deadpan sense of humor—the actor more than holds her own alongside the likes of Ben Stiller and Matt Dillon in the Farrelly brothers’ gross-out comedy. (She also earned her first Golden Globe nomination for the role.) Yes, you’ll remember the film for her, er, unconventional hair gel, but there’s also a wealth of late-’90s style inspiration, from her barrettes and micro shades to her denim, sleeveless knits, strappy party dresses, and, of course, that enviable layered bob.
In Her Shoes (2005)
Aimless wild child Maggie Feller (Diaz) is the freewheeling, irresponsible antithesis of her straight-laced older sister, Rose (Toni Collette), in Curtis Hanson’s touching family saga. There’s a certain steeliness and venom to the former that sets her apart from Diaz’s previous, more angelic creations—a younger sibling entitlement, a simmering resentment, a dangerous recklessness—but as we get to know her, her edges soften, revealing an anxious, fearful woman who’s never fully grown up. It’s a tightrope walk that she handles with flair.
The Holiday (2006)
Pour one out for Amanda Woods, the always unlucky-in-love, supremely unemotional, high-powered Hollywood executive who had to endure a cheating ex, trudging through the snow with all her luggage, driving past vans on narrow country roads, and the lack of adequate central heating in her tiny, picturesque Surrey cottage—while Kate Winslet got to literally jog through her LA mansion—all before she got a chance to romance Jude Law’s Mr. Napkin Head in Nancy Meyers’s Christmas staple. The “Mr Brightside” sequence sums up Diaz’s eternal appeal perfectly: She somehow manages to be both a stunningly beautiful, almost mythological creature and also entirely, hilariously relatable.
