Cameron Diaz had a dream entry into Hollywood when she was cast as Tina Carlyle in The Mask. Before her movie role, she had no intention of pursuing acting. She began her career in modeling and briefly relocated to Paris to further her modeling career.
Diaz was persuaded to audition for the Jim Carrey film by one of her modeling agents, and she caught the attention of director Chuck Russell. Her first movie turned into one of the highest-grossing movies in her career. She appeared in a string of comedy movies during the 1990s and 2000s, making her a prominent face in romcoms.
Interestingly, her highest-grossing movie came much earlier in her career. Fans would be surprised to know that her biggest box office hit was There’s Something About Mary, the popular comedy flick she starred alongside Ben Stiller in 1998.
She went on a hiatus from Hollywood in 2014 and made her return to acting in the 2025 Netflix movie, Back in Action. Diaz is also set to appear in more acting projects. Here are the top five movies in Diaz’s filmography, ranked based on their box office collections.
5. Knight and Day (2010)
Box Office: $262 million
Cameron Diaz collaborated with Tom Cruise for the second time in the action comedy film, Knight and Day. Diaz played June Havens, a classic car restorer, who gets caught up with Cruise’s secret agent character. The satirical action movie was helmed by James Mangold.
While critics praised the action sequences and the performances of Diaz and Cruise, many of them weren’t impressed with the film’s script. According to the website consensus on Rotten Tomatoes, the movie was “pure formula”.
Diaz even joined Cruise in doing a daring motorcycle stunt for the film. Diaz was also intrigued by her character, June, who evolves from someone unaware of her capabilities to someone who can drive, shoot, and fight people effortlessly (via The Mirror).
The film was made on a budget of $117 million, with Cruise being offered a share of revenue in exchange for a lower advance fee. The film became a sleeper hit at the box office, grossing $262 million worldwide.
Knight and Day is now available for streaming on Disney+, Hulu, and Prime Video.
4. Charlie’s Angels (2000)
Box Office: $264.1 million
One of Cameron Diaz’s most notable roles in the early 2000s was playing Natalie Cook in the action comedy film, Charlie’s Angels. She took one of the three lead roles in the film, alongside Lucy Liu and Drew Barrymore. In fact, her role in the film came via Barrymore, with whom she had been friends since their teen years.
The movie was a continuation of the television series of the same name, created by Ivan Goff and Ben Roberts. The movie was McG’s feature film directorial debut. It starred Bill Murray, Sam Rockwell, Tim Curry, Matt LeBlanc, Luke Wilson, and Kelly Lynch. Barrymore also served as a producer of the movie.
In the film, the three female superspy detectives investigate the kidnapping of an elite billionaire. It wasn’t the best effort of the three lead actresses, but it provided all the fun and the laughs that audiences wanted in the theaters. The film grossed $264.1 million at the box office.
The three actresses would return once again for a sequel, Charlie’s Angels: Full Throttle, which wasn’t nearly as good as the first film.
Charlie’s Angels is now available for streaming on Netflix.
3. My Best Friend’s Wedding (1997)
Box Office: $299.3 million
My Best Friend’s Wedding is a heartwarming watch, which we would love to go back to often. Julia Roberts‘ Julianne is the protagonist of the story, while Cameron Diaz plays a wealthy heiress who is engaged to Julianne’s best friend, Michael, played by Dermot Mulroney. Julianne arrives at this wedding with the intention of winning Michael’s heart.
If this plot appears to be a formulaic romcom storyline, you couldn’t be more wrong. It received widespread acclaim, particularly for subverting the tropes of this genre. While any other rom-coms of the era could’ve easily turned Diaz’s Kimmy into a villain to justify Julianne’s actions, this movie refuses to do so.
It was nominated for one Academy Award and three Golden Globe Awards. The film emerged as a global hit and an all-time classic romcom story, earning $299.3 million against its $38 million budget. While Diaz had a supporting role, her good luck charm at the box office in the late ’90s worked perfectly well for this movie.
My Best Friend’s Wedding is now available for rent on AppleTV and Amazon.
2. The Mask (1994)
Box Office: $351.8 million
Jim Carrey‘s 1994 flick, The Mask, is full of cartoonish chaos and gigs, and he pretty much carries the film on his shoulder. However, it was also a breakthrough role for Cameron Diaz. Carrey’s electric performance, coupled with his chemistry with Diaz, made the film into a memorable outing even three decades later.
Chuck Russell’s first film in the Mask franchise was based on John Arcudi, Doug Mahnke, and Mike Richardson’s comic book series, published by Dark Horse Comics. New Line Cinema wasn’t happy with Russell’s casting choice of Carrey and Diaz because they were both relatively unknown at the time. However, Russell was able to convince the studio and the rest was history.
The film had a budget of $18 million and made almost 20 times more with its worldwide gross of $351 million (via The Numbers). It is not just Diaz’s best comedy film, but it is also the movie that launched her career and made her a prominent sex symbol in the romantic comedies of the late 1990s and early 2000s. Diaz and Carrey didn’t return for the sequel movie.
The Mask is now available for streaming on Netflix and TBS.
1. There’s Something About Mary (1998)
Box Office: $369.9 million
Before he was the director of a critically acclaimed sci-fi drama like Severance, Ben Stiller was the funny guy from There’s Something About Mary. Cameron Diaz was one element that kept this film within the confines of a romcom and not a raunchy, gross-out comedy. Diaz gained critical acclaim for her performance in this movie.
Stiller’s Ted uses a private investigator to track down his high school sweetheart, Mary. However, this PI, played by Matt Dillon, turns the villain in his story when he starts dating Mary. The charming film won over many audiences with this simple premise. Diaz looked gorgeous as ever in the Farrelly brothers’ comedy, which earned $369.9 million against a $23 million budget.
There’s Something About Mary is now available for streaming on Hulu and YouTube TV.
What’s your favorite movie among these highest-earning movies from Cameron Diaz’s filmography? Let us know in the comments below!
