1. There’s Something About Mary (1998)

IMDB Rating: 7.1/10 | Rotten Tomatoes: 83%

Storyline: The film follows Ted Stroehmann (Ben Stiller), who is still in love with his high school prom date, Mary Jensen (Cameron Diaz), from thirteen years ago. He hires a private investigator, Pat Healy (Matt Dillon), to track her down, but Pat falls for her as well and gives Ted misleading information.

Major Performance: Diaz’s portrayal as the wacky and loveable Mary is damn near perfect. Her comedic timing is impeccable and she completely shines in this outrageous role. She is warm and sure of herself, never letting herself feel ashamed of who she is. Diaz’s performance has been widely acclaimed for her ability to balance broad physical humor with a genuine and tender portrayal of a character who, despite her quirks and various embarrassments, remains self-possessed and kind-hearted.

Major Performance: Cameron Diaz, who was already carving a niche for herself as a skilled and fearless comedienne, gives a grounded performance in a film that often veers into the outrageous. Her chemistry with Ben Stiller is excellent, often managing to find sweet, small moments amidst the broader bits of comedy, and making them feel true. This role required her to be funny, vulnerable, sweet, and able to deliver crude humor without losing the character’s essential kindness, and Diaz nailed it.

2. Vanilla Sky (2001)

IMDB Rating: 6.9/10 | Rotten Tomatoes: 42%

Storyline: This movie is about a successful publisher (Tom Cruise) who falls in love with the woman (Penelope Cruz) his friend (Cameron Diaz) introduces him to. However, a car accident changes everything and the man ends up disfigured, leading him down a dark path of confusion and self-discovery.

Major Performance: Vanilla Sky proved that Diaz is not merely a comedic actress but possesses a range that is both vast and complex. Her portrayal of Julianna, the jilted lover, is intense, revealing a simmering anger beneath a bubbly exterior. She plays the character’s vulnerability and desperation to chilling effect. It was her dramatic scene in the car with Cruise that likely secured her a nomination for Best Supporting Actress at the Golden Globe Awards.

Major Performance: With Vanilla Sky, Diaz stepped beyond her comedic comfort zone to deliver a role filled with tension, angst and pain. Her performance as Julianna shows her capability to handle dramatic roles of deep emotional intensity. Despite the mixed reviews of the film itself, critics universally praised Diaz’s portrayal, elevating her status as a versatile actress.

3. Gangs of New York (2002)

IMDB Rating: 7.5/10 | Rotten Tomatoes: 73%

Storyline: Gangs Of New York, directed by Martin Scorsese, is set in the mid-19th century, in the Five Points district of New York City. The film portrays the birth of organized crime in America through the story of a young man (Leonardo DiCaprio) seeking vengeance for his father’s death.

Major Performance: Cameron Diaz once again showcased her talent and range in this film as Jenny Everdeane. As a talented pickpocket and love interest to DiCaprio’s character, Diaz delivers a captivating performance. She nails the accents, physicality, and delivers a layered portrayal of a woman trying to survive a difficult and dangerous environment.

Major Performance: There is a distinct rawness to Jenny and Diaz radiates it through the entirety of the film. She acts with resilience and grit, matching every ounce of energy thrown at her by her costars Leonardo DiCaprio and Daniel Day Lewis. This role broke a lot of preconceptions about Diaz as an actor, proving she can hold her own in a heavy, drama-filled historical film.

4. Being John Malkovich (1999)

IMDB Rating: 7.7/10 | Rotten Tomatoes: 93%

Storyline: The film follows a struggling puppeteer (John Cusack) who stumbles across a portal into the mind of actor John Malkovich. Things get complicated when his wife (Cameron Diaz) becomes infatuated with the unique experience.

Major Performance: Cameron Diaz dives headfirst into the peculiar world of Being John Malkovich. She plays Lotte Schwartz, the frumpy, pet-obsessed wife to John Cusack’s character, and it’s a role that goes against her typical glamorous roles. Diaz delivers a knockout performance, truly embodying Lotte’s eccentricities and emotional struggles.

Major Performance: This film demonstrates Diaz’s range to excellent effect. Few actresses would be brave enough to play a part so restrained and physically unappealing, but she makes Lotte instantly memorable with her naturalistic, heartfelt performance. The role, in its oddity and complexity, could easily have veered into caricature but Diaz skillfully maintains her character’s humanity throughout.

5. My Best Friend’s Wedding (1997)

IMDB Rating: 6.3/10 | Rotten Tomatoes: 73%

Storyline: In this romantic comedy, Diaz plays Kimberly Wallace, a woman unknowingly competing with her fiancé’s best friend (Julia Roberts) for his affection. As she plans her wedding, the best friend tries everything she can to sabotage the marriage and win back her long-time love.

Major Performance: Diaz’s bubbly performance in My Best Friend’s Wedding is one that resonates with audiences. She plays Kimberly with a down-to-earth vulnerability that makes her so likeable, and it’s hard to root against her even though the film’s protagonist is trying to break up her relationship.

Major Performance: Diaz proves once again that she has a flair for comedy. There’s a sincerity and warmth to her character that makes her irresistible. Even as the second woman, she still manages to captivate the screen with her charm and energy. This role marked the beginning of a successful career for Diaz as a rom-com heroine.

6. The Mask (1994)

IMDB Rating: 6.9/10 | Rotten Tomatoes: 72%

Storyline: The Mask revolves around Stanley Ipkiss, an everyman who discovers a magical mask that transforms him into a suave, superpowered alter ego. Things get complicated when he falls for the beautiful nightclub singer, Tina Carlyle (Cameron Diaz), who is involved with a gangster.

Major Performance: Diaz’s film debut in The Mask was instant dynamite. Her innocent yet seductive portrayal of Tina Carlyle launched her into stardom overnight. Diaz playfully embodied the typically cliche’d “damsel in distress” role, and added her own unique flair to it, transforming an otherwise one-dimensional character into a vibrant, engaging presence.

Major Performance: Cameron Diaz is a revelation in The Mask. She exudes charisma and sex appeal, matched with a sweetness that endears her to audiences. The character’s journey from vixen to heroine is made believable by Diaz’s dedicated performance. She holds her own opposite Jim Carrey, adding charm and dynamism to the film.

7. In Her Shoes (2005)

IMDB Rating: 6.4/10 | Rotten Tomatoes: 75%

Storyline: Cameron Diaz plays Maggie, a sexy party girl who can’t hold down a job or make a commitment. When Maggie’s way of life gets her kicked out by her stepmother, she moves in with her estranged sister, Rose (Toni Collette), and ends up finding a family secret that brings the two of them closer together.

Major Performance: Diaz gives another impressive dramatic performance in In Her Shoes. As Maggie, she gets to explore the struggle of living in the shadow of her more grounded sister. It’s a deeper role for Diaz, one which she imbues with a calculated duality – frivolous exterior masking deep-seated vulnerability.

Major Performance: Diaz embraces this character, delivering a performance that is incredibly nuanced. She displays her craft in conveying genuine emotions and drawing sympathy during her character’s voyages of self-discovery and redemption. Her performance in In Her Shoes adds another layer to her acting persona, further cementing her status as a versatile actress.

8. Shrek (2001)

IMDB Rating: 7.8/10 | Rotten Tomatoes: 88%

Storyline: In the hugely popular animated film, Diaz voices Princess Fiona, who awaits her true love in a dragon-guarded castle. She is ultimately rescued by an unlikely hero – a grumpy ogre named Shrek.

Major Performance: Through Princess Fiona, Diaz added another dimension to her acting career, showcasing her talents as a voice actress. Her vocal performance brings out the tenderness and grit of Fiona, a character that ends up challenging the typical princess stereotype.

Major Performance: Diaz injected personality and depth into Fiona, facilitating her transformation from two-dimensional princess to a three-dimensional character with significant depth. Her ability to bring Fiona to life with just her voice shows her versatility as an actress and her performance became a big part of why viewers fell in love with the Shrek movies.

9. Bad Teacher (2011)

IMDB Rating: 5.6/10 | Rotten Tomatoes: 44%

Storyline: In Bad Teacher, Cameron Diaz plays Elizabeth Halsey, a foul-mouthed, ruthless, and inappropriate junior high teacher. She does not care about her students and only takes up teaching to fund her breast implants. Her plans change when she meets a wealthy substitute teacher and goes head-to-head with a popular colleague for his attention.

Major Performance: Bad Teacher is a showcase of Diaz’s fearless knack for comedy. She is bold, absorbing, and flamboyantly terrible as the unapologetically lazy and cunning Elizabeth Halsey. Diaz’s performance is an absolute comedic tour-de-force, making her unlikable character irresistibly entertaining.

Major Performance: Diaz brilliantly embraces the vulgarity and ruthlessness of her character. She manages to be both hilarious and honest, bending the stereotype of a caring and devoted teacher to create her own unique and unforgettable comic character. This performance proves once again that Diaz can carry a movie with her charisma and comedic timing.

10. The Holiday (2006)

IMDB Rating: 6.9/10 | Rotten Tomatoes: 49%

Storyline: The Holiday is a romantic comedy that follows two women (Cameron Diaz and Kate Winslet) who decide to swap houses for Christmas after experiencing guy-problems. Cameron Diaz plays Amanda Woods, a driven career woman who finds love in an unexpected place.

Major Performance: Diaz is charming and relatable in The Holiday. Her portrayal of a successful woman unable to cry and struggling with love touches the audience right from the beginning. Her comic timing and effortless charm bring Amanda Woods to life and her performance is a key factor in making The Holiday a feel-good festive classic.

Major Performance: Diaz remarkably conveys her character’s emotional journey – someone who is initially emotionally closed-off, but eventually manages to open up to the possibility of love. She consistently captivates the audience with her heartfelt and bubbly performance, ultimately accomplishing the task of making viewers fall in love with her character. The Holiday elite, the way Diaz plays Amanda, sustained enough sweetness to melt the most frozen of hearts and further exemplifies her strong prowess in romantic comedies.