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).