Best friends come in all shapes and sizes, but Hollywood decided that having a very specific « quirky best friend » was a must-have in romantic comedies. The quirky best friend is there to support the ingénue in their quest for self-discovery and/or love. The quirky best friend doesn’t typically have a major impact on the narrative or have a fleshed-out story of their own, mostly serving as a cheerleader or moral compass to the lead. The quirky best friend isn’t as « conventionally attractive » and they are often overlooked in favor of the main romantic storyline.

Quirky best friends might act as supporting characters, but some effectively steal scenes from the leading rom-com queens, elevating the material beyond a shallow trope. The following actors’ talents have uplifted the romantic comedies they performed in, some stars shining so brightly that they are now leads in their own right. While the character trope still exists in Hollywood films, these fabulous quirky best friends have supported the leads’ journeys throughout the years, and won a place in viewers’ hearts. If only everyone had friends like that.

10 Lizzy Caplan

Quirky Best Friend: Janis Ian in ‘Mean Girls’ (2004)

If the black eyeliner doesn’t scream it, Lizzy Caplan‘s unkempt hair and « Rubbish » tee will: Janis is different. Originating the role of Janis in 2004’s Mean Girls, Lizzy Caplan played the quirky best friend (along with Daniel Franzese‘s Damian) to Lindsay Lohan‘s hero, Cady. Janis served as a stand-in for the honest version of Cady before she turns into a Plastic; she says what everyone is thinking, sometimes brutally so. While Cady often overlooks Janis’ past demons (Regina) and successes (her art show), Caplan’s skilled take portrays the hurt and vulnerability of such a seemingly cold-hearted character.

After stealing scenes from Lohan and the success of Mean Girls, Lizzy Caplan played Kate Hudson‘s bestie in My Best Friend’s Girl, the family screw-up in Save the Date, and a former high school friend and cokehead in Bachelorette. Caplan is now a fixture on television, her talent landing her a stand-out 6-episode role in the steamy True Blood, a spot in the hilarious ensemble of Party Down, the co-lead of Showtime’s Masters of Sex, and the role that Kathy Bates originally made famous, Annie Wilkes, in the prequel TV series Castle Rock.

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9 Heather Matarazzo

Quirky Best Friend: Lilly Moscovitz in ‘The Princess Diaries’ (2001)

After making her debut in the indie cult classic, Welcome to the Dollhouse, Heather Matarazzo starred alongside Anne Hathaway in The Princess Diaries franchise. As Lilly, Matarazzo supported Hathaway’s Mia as she transitioned from a frizzed-out nerd to sleek royalty. She represented what Mia used to be, before her make-over and proper training. Lilly is a good friend to Mia, a confidante despite Mia increasingly neglecting their friendship. Proud and supportive, Lilly represents the « angel » side of Mia, while antagonistic bully Lana (Mandy Moore) is Mia’s « devil. »

Heather Matarazzo reunited with co-star Mandy Moore for Saved, in which she played the latter’s lackey with an awkwardly funny, holier-than-thou attitude. In Sorority Boys, Matarazzo played Katie, a member of a sorority consisting entirely of quirky best friend-types and used an obnoxious laugh to comedic effect – an outsider even among misfits. Heather Matarazzo has since moved into horror territory with a gut-wrenching role in Hostel Part II and a bit part as Randy’s sister in Scream 3, which she reprised in 2022’s Scream.

The Princess Diaries

Release Date

August 3, 2001

Runtime

1 hr 55 min

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8 Stacey Dash

Quirky Best Friend: Dionne Davenport in ‘Clueless’ (1995)

With stylish, almost matching outfits, Stacey Dash‘s Dionne and Alicia Silverstone‘s Cher in Clueless are friendship goals. Together, they rule high school, give a makeover to the even quirkier Tai (Brittany Murphy), and play matchmaker to their two lonely teachers. Unlike some quirky best friends, Dionne has a nice arc to her character throughout the film, especially with her on-and-off-again boyfriend Murray (Donald Faison). Despite being overshadowed by Cher and Josh’s (Paul Rudd) budding relationship, Dionne and Murray thoughtfully transform from bickering teens into a more mature couple (as much as they can as high schoolers).

After the booming success of Clueless, Stacey Dash continued her role of Dionne alongside Faison’s Murray in the Clueless television series. While Silverstone did not return to the IP, Dash still had charming chemistry with Rachel Blanchard, who stepped into the role of Cher. Running for 62 episodes, the series ended in 1999. In 2003, Dash starred with Gwyneth Paltrow in View from the Top, and reteamed with Clueless writer/director Amy Heckerling and costar Paul Rudd in the Michelle Pfeiffer vehicle, I Could Never Be Your Woman. Stacey Dash, unfortunately, hasn’t had major success on the big screen since her iconic turn in Clueless, but in 2016 she made an appearance in the infamous Sharknado franchise.

Clueless

Release Date

July 19, 1995

Director

Amy Heckerling

Runtime

97

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7 Bonnie Hunt

Quirky Best Friend: Kate in ‘Only You’ (1994)

She was in the room when Iron Man fell in love with Aunt May… Kind of. Bonnie Hunt was a go-to quirky best friend in the 1990s, which found her starring alongside a young Robert Downey Jr. and Marisa Tomei in Only You. The epitome of supportive, Hunt’s charming, subtle humor and soft, maternal demeanor made her an excellent friend as Tomei’s lead chased a decades-old Ouija Board prediction. Hunt provided a grounded moral compass, along with witty remarks, and sat on the sidelines as the romantic pairing found love.

Bonnie Hunt also got to hear one of the most romantic quotes from a film: « You complete me. » Although those words were directed by Tom Cruise to lead Renée Zellweger and not to Hunt. Instead, Hunt was playing Zellweger’s sister and support system in Jerry Maguire. The comforting presence that Bonnie Hunt displayed in these rom-coms easily helped her flex her dramatic muscles as « the wife » trope in Random Hearts and The Green Mile, as well as let loose in family comedies like Jumanji and Cheaper by the Dozen. Hunt has truly taken advantage of her likability in her voiceover career, which includes mega-franchises Cars and Toy Story.

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6 Christina Applegate

Quirky Best Friend: Courtney Rockcliffe in ‘The Sweetest Thing’ (2002)

While Christina Applegate began her career as the blonde bombshell type, she provided some great quirky best friend characters in the early 2000s. One of her best BFF roles was Courtney in the Cameron Diaz-led The Sweetest Thing. Providing both thoughtful insight and gross-out humor, Courtney is the type of character that should have been the lead. While the script actually provides her side character with a pretty thorough arc, Applegate elevates the material simply through her actions; she will speak to various men differently on purpose, knowingly playing a game. Applegate allows Courtney’s vulnerability to shine through when she finally finds a man she has feelings for.

Applegate later popped up as a frenemy to Gwyneth Paltrow in View from the Top, in which she was free to play up her sassiness; she later tapped back into this mode in Bad Moms. In 2010’s Going the Distance she played Corinne, a more grounded best friend, and sister to Drew Barrymore‘s love-lorn Erin. Free from the constraints of the « love interest » role, Corinne has a more colorful personality than Erin, bouncing between sweet words of encouragement and deadpan raunchy humor which captivated audiences.

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5 Leslie Mann

Quirky Best Friend: Debbie in ‘Knocked Up’ (2007)

Leslie Mann is quirky. She may look like a « conventionally pretty » actor, but her off-beat sense of humor, higher-pitched voice, and comedic sensibilities make her a great quirky best friend. Her magnetic energy was perfect for leading the cartoonish George of the Jungle, but her supporting role in Big Daddy showed just how funny and sassy she could be. Mann went head-to-head with Adam Sandler as his love interest’s disapproving sister, leading to a small but memorable gig as a very drunk clubgoer in The 40-Year-Old Virgin.

Married to comedy legend Judd Apatow, Mann also appears in many of his films, bouncing between leading roles and supporting ones. One of her best quirky best friend (and sister) roles was Debbie in Knocked Up, in which she was the sounding board for newly pregnant Alison (Katherine Heigl). As Debbie, Mann injected the character with more charm and likability than the film’s lead, even when having a hysterical meltdown over her marriage to Pete (Paul Rudd). Mann and Rudd as Debbie and Pete were so liked, in fact, that a sequel five years later, This Is 40, featured them in the starring roles and Mann in one of her best films.

Knocked Up

Release Date

June 1, 2007

Director

Judd Apatow

Runtime

129

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4 Joan Cusack

Quirky Best Friend: Cyn in ‘Working Girl’ (1988)

After a brief 17-episode run on Saturday Night Live, Joan Cusack found herself as an in-demand quirky best friend. 1988’s Working Girl featured Cusack’s Cyn stealing the show from Melanie Griffth‘s more traditional and conservative Tess. After Tess finds out about two betrayals (her boyfriend and her boss), Cyn plays the little devil on her shoulder, urging her to get revenge on her boss as well as cut her hair into a new confidence-inspiring ‘do. Cyn is the encouragement Tess needs to get her life back.

Joan Cusack’s secondary characters tend to outshine the main ones due to her relatability and onscreen charisma. She perfected the best friend role (both grounded and satirical), entertaining viewers in films like Nine Months, Two Much, Mr. Wrong, Grosse Pointe Blank, and A Smile Like Yours. Not only that, but she also took a backseat to the romance between Richard Gere and Julia Roberts in Runaway Bride, and Kate Hudson and rom-com king John Corbett in Raising Helen. And when this bridesmaid finally gets to be a bride as the betrothed in In & Out, her intended groom (played by Kevin Kline) comes out as gay.

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3 Rebel Wilson

Quirky Best Friend: Fat Amy in ‘Pitch Perfect’ (2012)

In 2011, Australian comedian Rebel Wilson got her breakout gig in the U.S. in Bridesmaids. She made such a splash in her brief role that she landed a supporting gig in the super-successful Pitch Perfect franchise. Using the moniker « Fat Amy, » Wilson’s character is confident, crass, and over-the-top – but she’s only one of the « weird » ones in the film’s a capella group. Amy is quick with witty remarks, often delivered in Wilson’s classic dead-pan, and inspiring with her encouragement; she helps liberate the other singers of the Bellas. Peppered throughout the franchise, Amy gets a love interest of her own, but that relationship is played for laughs instead of sincere like the leads’.

Rebel Wilson again played a quirky best friend in How to Be Single. Starring Dakota Johnson, Leslie Mann, and Alison Brie, the film featured Wilson as Robin, a party girl and one-night-stand enthusiast. Robin doesn’t have much backstory or plot of her own; she serves to challenge Alice’s (Johnson) way of thinking and progress her journey. In 2019, Wilson deconstructed this rom-com trope of the quirky best friend in Isn’t It Romantic. In the charming film, Wilson upgraded her best friend persona into the lead of her own romantic comedy, and it was well worth the wait.

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2 Kathryn Hahn

Quirky Best Friend: Michelle Rueben in ‘How to Lose a Guy in 10 Days’ (2003)

Kathryn Hahn has been stealing scenes from leading ladies since her breakout role in 2003’s How to Lose a Guy in 10 Days. Her relatable « everywoman groundedness » combined with her willingness to ham it up made her shine alongside rom-com titans Kate Hudson and Matthew McConaughey. Viewers could see themselves having a friend like her – or relating directly to her; not everyone can be Hudson. Hahn followed this up with Win a Date with Tad Hamilton, playing second fiddle to Kate Bosworth, and The Holiday, in which she took a backseat to both Cameron Diaz and Kate Winslet.

Hahn’s over-the-top comedic work in Step Brothers proved that she could stand toe-to-toe with Will Ferrell and John C. Reilly, but it wasn’t until Bad Moms and A Bad Moms Christmas that Hahn fully transitioned into a star. Still playing the quirky (and slightly inappropriate) mom in the group, Hahn’s outlandish style suited her go-for-broke attitude and she made viewers want to party with her. Now, she is stepping out of the shadows and starring in moving, emotional series like Mrs. Fletcher and Tiny Beautiful Things, as well as headlining her own MCU spin-off series, Agatha: Darkhold Diaries, from WandaVision.

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1 Judy Greer

Quirky Best Friend: Lucy Wyman in ’13 Going on 30′ (2004)

In the 2000s, Judy Greer was everyone’s quirky best friend. She supported leading ladies like Jennifer Lopez in The Wedding Planner, Jennifer Garner in 13 Going on 30, and Katherine Heigl in 27 Dresses. The irony of playing the quirky best friend (again) to a perpetual bridesmaid in 27 Dresses was also not lost on Greer. Using her deadpan delivery to excellent effect, Greer ranges from sarcastic in frenemy roles to sincere in heartfelt ones, making her relatable to viewers, often more so than the leading lady. Her characters are not « typically beautiful, » nor do they have much of an arc or backstory of their own. But with Greer’s expertise, each one pops off the screen.

Greer also has impressive insight into her prolific filmography as the quirky best friend. When asked why she often gets typecast in these kinds of roles, she said to Conan O’Brien that she is good at « boosting the ego of someone who is slightly more attractive than me, but less funny. » Speaking of her sense of humor, Greer has written a book and made a short film that embrace and poke fun at her onscreen quirky best friend persona. In another interview, Judy Greer explained that secondary characters are often saddled with delivering the backstory of a film. If an actor is funny, that boring exposition goes down better with the viewer, and the focus stays on the leads instead of any clunky dialogue. Thankfully, Greer has transitioned out of these friend roles and now stars in heavy-hitters like the new Halloween films, Jurassic World, and Ant-Man and the Wasp.

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