Cameron Diaz’s 10 Best Movies, Ranked

Warning: This article discusses topics of suicide and terminal illnesses.

Cameron Diaz is a fabulously talented actress with a scope of incredible movies from her long-spanning career. Diaz’s acting kicks off with the hilarious Jim Carrey film The Mask, making her debut at just 21, but in recent years, she is best known for her performance in Will Gluck’s remake of Annie. Although she has retired from the silver screen before, she is still remembered and is an actress that many audiences hoped would return. Since her start in the ‘90s, Cameron Diaz’s net worth has soared from her most memorable roles.

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Thankfully, Cameron Diaz’s movie comeback is finally happening. The actress is due to appear opposite Keanu Reeves in Apple TV’s Outcome, and she is once again lending her voice to Princess Fiona in the fifth installment of the Shrek franchise. While Diaz is generally prominent in romantic comedy movies, some of her best projects see her taking on more dramatic and profound characters. Cameron Diaz has many amazing movies, but some are better than others.

10 What Happens In Vegas (2008)

Role: Joy McNally

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What Happens in Vegas isn’t one of the best rom-coms of all time, but it is a very memorable one. Diaz stars as Joy McNally, a woman who meets Ashton Kutcher’s Jack Fuller Jr. in Las Vegas and drunkenly marries him. However, when Jack wins a huge fortune on a slot machine, which Joy provides the quarter for, they try to force their marriage to work for six months in order to keep half of the winnings each. Kutcher and Diaz’s chemistry is excellent, and both demonstrate the constant bickering and underlying tension between their characters brilliantly.

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PG-13

Director Tom Vaughan Release Date May 9, 2008 Cast Cameron Diaz , Ashton Kutcher , Rob Corddry , Lake Bell , Jason Sudeikis , Treat Williams , Deirdre O’Connell , Michelle Krusiec , Dennis Farina , Zach Galifianakis , Queen Latifah , Krysten Ritter , Ricky Garcia , Andy Daly , Benita Robledo , Dennis Miller , Amanda Setton , Toni Busker , Jessica McKee , Ricardo Walker Runtime 99 minutes Expand

What Happens in Vegas is from the relatively early days of Ashton Kutcher’s career, but it isn’t the first film of his where he plays a struggling groom, having appeared in 2003’s Just Married, and this shows in his rapport with Diaz. While the critic reviews for What Happens in Vegas aren’t the best, Diaz still stands out. Joy is quite unlikeable when she is first introduced, but her later growth makes her easy to root for. Portraying Joy proves that Diaz can take on any type of character easily, even if the film’s story doesn’t do her any favors.

9 My Best Friend’s Wedding (1997)

Role: Kimmy Wallace

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My Best Friend’s Wedding is a classic title in which Diaz stars as Kimmy Wallace, the fiancé of the closest companion to Julia Roberts’ Jules Potter. Unbeknownst to Kimmy, Jules realizes she is in love with her best friend, Dermot Mulroney’s Michael O’Neal, and plans to capture his heart. Kimmy is a fascinating character for Diaz, who is often cast as a romantic lead.

While Diaz isn’t supposed to be the main focus, she is still a scene stealer.

However, her supporting role in My Best Friend’s Wedding is what cemented her in the world of Hollywood cinema, and her multiple accolade wins and nominations for Kimmy prove this. While Diaz isn’t supposed to be the main focus, she is still a scene stealer. Kimmy is enthusiastic and rather sweet, which makes her unique in comparison to other rom-com characters who serve as a romantic obstacle.

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Director P.J. Hogan Release Date June 20, 1997 Cast Julia Roberts , Dermot Mulroney , Cameron Diaz , Rupert Everett , Philip Bosco Runtime 105 Minutes

Kimmy’s most awkward moments allow Diaz to show off her comedic talents, though, such as her painfully tone-deaf performance at the karaoke bar and her final rant at Jules at the climax of the movie. Overall, My Best Friend’s Wedding is a prime example of Diaz’s ability to grab the spotlight naturally, even when she isn’t the protagonist.

8 Charlie’s Angels (2000)

Role: Natalie Cook

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Diaz plays Natalie Cook in the Charlie’s Angels movies from the 2000s, a continuation of the hit 1970s TV show. She stars in the 2000 title, as well as the 2003 sequel, Charlie’s Angels: Full Throttle, alongside Drew Barrymore as Dylan Sanders and Lucy Liu as Alex Munday.

Diaz, Barrymore, and Liu are outstanding as the Angels, and the trio brings the action-packed world of Charlie’s Angels to life beautifully. There is a lot of argument about whether Elizabeth Banks’ Charlie’s Angels is better than the 2000 movie, but Natalie as a character cements that Diaz’s version is superior.

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PG-13

Director McG Release Date November 3, 2000 Cast Drew Barrymore , Cameron Diaz , Lucy Liu , Bill Murray , Sam Rockwell , Kelly Lynch , LL Cool J , Matt LeBlanc , Tim Curry , Crispin Glover , Luke Wilson , Tom Green Runtime 98 Minutes

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While all three of them are prominent figures throughout the film, Natalie’s characterization is the very best. Diaz’s fight scenes in Charlie’s Angels are spectacular, and her wild stunts are incredibly memorable. Natalie is also a complete badass, yet she approaches everything with a bubbly attitude and a solid sense of humor, which proves she is someone who shouldn’t be messed with. Diaz isn’t known for being an action star, but in Charlie’s Angels, it’s easy to forget that she isn’t.

7 The Mask (1994)

Role: Tina Carlyle

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The Mask is a notable title out of Jim Carrey’s best movies, in which Diaz plays Tina Carlyle, who develops a crush on Jim Carrey’s Stanley Ipkiss despite being in a relationship with Peter Greene’s Dorian Tyrell. The blonde bombshell is a crucial character in The Mask, and she is a very layered character. Lounge singer Tina is full of sass and confidence but also has a sweet side. She even likes Stanley as himself, without the mask. She grabs Stanley’s attention immediately after he spots her for the first time, and Diaz embraces the role of leading lady perfectly.

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PG-13

Director Chuck Russell Release Date July 29, 1994 Cast Richard Jeni , Peter Riegert , Peter Greene , Cameron Diaz , Amy Yasbeck , Jim Carrey Runtime 101 minutes

What’s so interesting about Diaz in The Mask is that she has zero acting experience and is only 21 years old. Her casting in the film is astounding, and her lack of previous performances makes her career breakthrough in The Mask even more impressive. Tina is a great and eye-catching character from her first scene. She is intriguing and addictive to watch, and many of The Mask’s funniest quotes are aimed toward her. Diaz’s interactions with both Carrey and Greene are amazing, too, and she holds her own against two titans of industry.

6 The Holiday (2006)

Role: Amanda Woods

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The Holiday is one of the best Christmas movies of all time, and a large chunk of the film’s success is because of Diaz. The actress portrays Amanda Woods, a young woman who escapes to the English countryside after she discovers her boyfriend cheating. While she tries to enjoy her heartbreak vacation, Amanda unexpectedly meets and falls for Jude Law’s Graham.

Related Cameron Diaz Almost Didn’t Star In The Mask

Cameron Diaz almost didn’t star opposite Jim Carrey in The Mask back in 1994, but it’s the part that became the actress’ breakout role.

The chemistry between Law and Diaz is absolutely spectacular, and their twist-of-fate love story is even more believable because of their performances. While Jack Black and Kate Winslet’s narrative is good, Diaz’s acting proves that the UK storyline in The Holiday is better.

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Director Nancy Meyers Release Date December 14, 2006 Cast Cameron Diaz , Jude Law , Jack Black , Kate Winslet Runtime 138 Minutes

Amanda’s experiences in England are hilarious and provide some of the funniest moments throughout the film, such as her driving on the wrong side of the road or her drunken dancing. Amongst the laughter, however, the development of her relationship with Graham is captivating and very romantic, which highlights Diaz’s versatility as a dramatic and comedic actress.

5 Shrek (2001)

Role: Princess Fiona

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One of Diaz’s best-known roles is Princess Fiona in every Shrek movie, the first being the 2001 release, which introduces audiences to the far-from-normal fairytale world. Fiona is also Diaz’s most significant voice acting role, and while she doesn’t get to show off her skills with facial expressions or body language, she is still prominent.

Diaz is a breath of fresh air as Fiona, and the actress does a fabulous job of voicing her, who is vastly different from the average princess.

Diaz is a breath of fresh air as Fiona, and the actress does a fabulous job of voicing her, who is vastly different from the average princess. Diaz’s comedic timing is fantastic, and she isn’t afraid to embrace Fiona’s flaws in her performance. She continues to demonstrate this in further installments of the franchise, too.

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Director Vicky Jenson , Andrew Adamson Release Date May 18, 2001 Cast Cameron Diaz , Mike Myers , Eddie Murphy , John Lithgow Runtime 90 minutes

Fiona’s character consistently grows and improves in every film, and she effortlessly tackles life-changing events like her father’s death and becoming a mother. Diaz is due to reprise her role as Princess Fiona in the upcoming Shrek 5, which is scheduled to arrive in theaters on July 1, 2026, and audiences are excited to see what happens next to her and the titular character.

4 Vanilla Sky (2001)

Role: Julianna “Julie” Gianni

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Diaz only has a small role in Vanilla Sky, but it is still one that keeps the actress at the forefront of viewers’ minds. The actress plays Julie Gianni, the lover of Tom Cruise’s David Aames, who is desperate to keep their relationship strong. Vanilla Sky jumps between dreams and reality, and Julie’s jealous rage and car crash are what kick off these events. Even though Diaz isn’t a main character, she still has several major moments. Julie dies twice in Vanilla Sky, once by suicide and again when David suffocates her, and Diaz’s performances in these scenes are stellar.

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Director Cameron Crowe Release Date December 14, 2001 Cast Tom Cruise , Penelope Cruz , Kurt Russell , Jason Lee , Noah Taylor , Cameron Diaz Runtime 136 Minutes

The most impressive thing about Diaz’s limited role in Vanilla Sky is the award nominations she has for it. It’s initially a surprise that Diaz is a Golden Globe and Screen Actors Guild nominee, but upon seeing her performance, it makes a lot of sense. Julie’s intense behavior dominates the screen, which is only possible because of Diaz’s terrifying yet emotional portrayal. Vanilla Sky is a fascinating title in Diaz’s filmography, but it highlights her strengths as an actress and that she is unstoppable in any role, big or small.

3 My Sister’s Keeper (2009)

Role: Sara Fitzgerald

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My Sister’s Keeper is deeply profound and is a sad movie guaranteed to make anyone cry. Diaz plays Sara Fitzgerald in the film, the mother of Sofia Vassilieva’s Kate, a teenage girl slowly and painfully dying from acute promyelocytic leukemia. Sara is a complicated character who allows Diaz to provide one of her very best performances ever, and the struggles that she faces while trying to keep her family together are astounding. My Sister’s Keeper presents a compelling ethical debate about euthanasia and savior siblings, and Sara’s heartbreaking attempts to keep Kate alive play into this.

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Director Nick Cassavetes Release Date June 26, 2009 Cast Cameron Diaz , Abigail Breslin , Sofia Vassilieva , Alec Baldwin , Jason Patric Runtime 109 Minutes

Diaz establishes herself as a powerful dramatic actress in My Sister’s Keeper. She is fantastic in the film’s most intense scenes, such as when her youngest daughter, Abigail Breslin’s Anna, hires a lawyer in the hopes of emancipating herself and stopping providing medical assistance to Kate. Sara discovering Kate wants to die is by far the most impactful moment in the movie, and Diaz is often celebrated for her performance in this scene. My Sister’s Keeper is a notable title from Diaz’s career because it’s not a rom-com and is very serious, but she still shines.

2 There’s Something About Mary (1998)

Role: Mary Jensen

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Diaz’s first Golden Globe nomination comes from her performance as the titular character in There’s Something About Mary. Diaz’s portrayal of Mary Jensen, a young woman who receives a ridiculous amount of attention from four men who simply do not leave her alone, is nothing short of incredible. It’s hard not to feel sorry for Mary, who is merely looking for a nice guy and a calm and stable relationship.

The guys’ constant attempts to win her affection result in some of the cringiest moments from ‘90s comedies, but Mary’s patience and perseverance are admirable. However, Mary has her own awkward moments, too. There’s Something About Mary’s famous hair gel scene is brilliantly funny and shows Diaz at her most comical.

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Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott Runtime 119 Minutes

Her rapport with Ben Stiller’s Ted Stroehmann is also very strong, and examining Mary through Ted’s love-struck point of view makes Diaz look even better. There’s Something About Mary 2 has never happened, sadly, but if there is any character that viewers are hoping to see Diaz bring back to the silver screen, it’s Mary Jensen.

1 Being John Malkovich (1999)

Role: Lotte Schwartz

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Being John Malkovich is the crown jewel in Cameron Diaz’s filmography. The eerie and mind-bending sci-fi movie is a wild and groundbreaking title in the genre, and Diaz’s performance as Lotte Schwartz attributes this. Lotte is the long-suffering wife of John Cusack’s Craig, and Diaz is completely unrecognizable in this role, both in physical appearance and personality.

Diaz swaps out her usual blonde hair for brown straggly strands, and Lotte’s raw vulnerability is nothing short of perfection. Being John Malkovich is Diaz’s most celebrated movie, earning her two nominations for Best Supporting Actress at the Golden Globes and the BAFTAs.

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Director Spike Jonze Release Date October 29, 1999 Cast John Cusack , John Malkovich , Cameron Diaz , Catherine Keener Runtime 113 Mins

However, considering her astonishing performance as the pet-obsessed woman, she is deserving of more. Some of Diaz’s best scenes in Being John Malkovich are when she is consumed by the titular character, which makes her performance doubly layered, as she is playing two people at once. It’s still nonsensical that Cameron Diaz isn’t an Oscar nominee for this film, but it remains her very best piece from across her established career.

Cameron Diaz

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Category: Entertainment