What’s Not to Love About Cameron Diaz and Her Iconic Rom-Coms?

Cameron Diaz turns 49 August 30th and, to celebrate, we’re looking back on some of her most iconic romantic comedy roles.

By Nami Hoffman Aug 30, 2021 10:00 AMTags

There is something about Cameron Diaz. Especially today. Oh, that's right, it's her 49th birthday!

Though currently retired, the mom of daughter Raddix has a resume that is a work of art worth celebrating. Over two decades, she transformed into Lotte Schwartz in 1999's Being John Malkovich, Natalie Cook in the 2000's Charlie's Angels and voiced Fiona in all of the Shrek movies. Truly, what can't she do? We don't know. 

And as much as we loved her in those iconic roles, we want to especially highlight her illustrious romantic comedy history, in which she has played characters who ranged from sweet to spicy (and dare we even say raunchy?) and made her co-stars seem just as obsessed with her as we always are. 

The list of our favorite rom-coms our favorite heroine has starred in seems endless, but we are going to give it our best shot and applaud them all.

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Cameron Diaz's Best Roles

So, in honor of Diaz's big day, keep scrolling...

1994: The Mask

At just 21, Cameron Diaz made her acting debut in the less-than-conventional romantic comedy The Mask. She played Tina Carlyle, the love interest of Jim Carrey's character Stanley Ipkiss, who also had a bizarre mask persona. This out-of-the-box flick put Diaz on the path to superstardom.

1996: She's The One

Focusing more on the dynamics of brotherhood, She's The One follows brothers Mickey (Edward Burns) and Francis (Mike McGlone). Mickey, a taxi driver, marries a woman he had picked up just a few days before. Meanwhile, Francis is worried about being unfair to his mistress, Heather (Diaz), who is the ex-fiancée of Mickey. You could say it's complicated.

1997: My Best Friend's Wedding

When Julianne Potter (Julia Roberts) finds out her best friend (Dermot Mulroney) is about to marry Kim (Diaz), she has the sudden realization that she wants to be with him. And that can only mean one thing: drama. Despite all of Julianne's efforts, Kim seems to be perfect—and in the end, Julianne learns that sometimes friends aren't supposed to be anything more than just friends.

1998: There's Something About Mary

Mary (Diaz) has an allure that no man in this movie can seem to resist. So much so that a pizza guy pretends to be an English architect who needs crutches to get her attention. But can you blame them?

2002: The Sweetest Thing

The Sweetest Thing may be a romantic comedy, but the love between friends comes first. This raunchy film follows Christina (Diaz) on her quest for Mr. Right Now, not Mr. Right. Once she meets Peter, she changes her mindset and takes a road trip with her friend Courtney (Christina Applegate) to find him. The duo experience maggots, glory holes and an iconic duet of the Piña Colada Song to only find out Peter is getting married that day.

2006: The Holiday

This 2006 classic is a Christmas favorite with a star-studded cast. Signing up to do a house swap, Amanda (Diaz) and Iris (Kate Winslet) find love in each other's homes. This movie is a must-watch when you want to get into the holiday spirit.

2008: What Happens in Vegas

What happened in Vegas doesn't stay in Vegas for the newlyweds Joy (Diaz) and Jack (Ashton Kutcher), who cannot agree on who a 3 million jackpot belongs to. Agreeing to try to be a real married couple for six months, they spend their time scheming instead. But will their forced proximity make them fall in love despite their devious tricks?

2011: Bad Teacher

Dumped by her rich fiancée, Ms. Halsey (Diaz) sets her sights on substitute teacher Scott Delacorte (Justin Timberlake), especially once she finds out he comes from a wealthy family. On a mission to win a bonus to fund a boob job to impress him, she begins a rivalry with fellow teacher Ms. Squirrel (Lucy Punch).

2014: Sex Tape

Spicing up your love life can lead to disaster. Just ask Jay and Annie (Jason Segel and Diaz, respectively). When they realize their sex tape has been uploaded to iPads they have gifted to friends, they go on a mission to collect them back.

2014: The Other Woman

What happens when one mistress meets the wife, and then another mistress? The movie The Other Woman. Carly (Diaz), Kate (Leslie Mann) and Amber (Kate Upton) form an unlikely friendship to take down their shared, cheating partner Mark (Nikolaj Coster-Waldau).

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