Best friends come in all shapes and sizes, but Hollywood decided that having a very specific “quirky best friend” was a must-have inromantic 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, mostlyserving 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 theleading rom-com queens, elevating the material beyond a shallow trope. The following actors' talents haveuplifted 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.
10Lizzy 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 isdifferent. Originating the role of Janis in2004’sMean Girls, Lizzy Caplan played the quirky best friend (along withDaniel Franzese’s Damian) toLindsay 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 takeportrays the hurt and vulnerability of such a seemingly cold-hearted character.
After stealing scenes from Lohan and the success ofMean Girls, Lizzy Caplan playedKate Hudson’s bestie inMy Best Friend’s Girl, the family screw-up inSave the Date, and a former high school friend and cokehead inBachelorette. Caplan is now a fixture on television, her talent landing her a stand-out 6-episode role in thesteamyTrue Blood, a spot in thehilarious ensemble ofParty Down, the co-lead ofShowtime’sMasters of Sex, and the role thatKathy Batesoriginally made famous,Annie Wilkes, in the prequel TV seriesCastle Rock.
Mean Girls
Watch on Paramount+
9Heather 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 Matarazzostarred alongsideAnne HathawayinThe Princess Diariesfranchise. 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-starMandy MooreforSaved, in which she played the latter’s lackey with an awkwardly funny, holier-than-thou attitude. InSorority 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 inHostel Part IIand a bit part as Randy’s sister inScream 3, which she reprised in 2022’sScream.
The Princess Diaries
Watch on Disney+
8Stacey Dash
Quirky Best Friend: Dionne Davenport in ‘Clueless’ (1995)
With stylish, almost matching outfits,Stacey Dash’s Dionne andAlicia Silverstone’s CherinCluelessare 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 ofClueless, Stacey Dash continued her role of Dionne alongside Faison’s Murray in theCluelesstelevision series. While Silverstone did not return to the IP, Dash still had charming chemistry withRachel Blanchard, who stepped into the role of Cher. Running for 62 episodes, the series ended in 1999. In 2003, Dash starred withGwyneth PaltrowinView from the Top, and reteamed withCluelesswriter/directorAmy Heckerlingand costar Paul Rudd in theMichelle Pfeiffervehicle,I Could Never Be Your Woman.Stacey Dash, unfortunately, hasn’t had major success on the big screen since her iconic turn inClueless, but in 2016 she made an appearance in the infamousSharknadofranchise.
7Bonnie 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 Huntwas a go-to quirky best friend in the 1990s, which found her starring alongside a youngRobert Downey Jr.andMarisa TomeiinOnly You. The epitome of supportive, Hunt’scharming, subtle humor and soft, maternal demeanormade 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 byTom Cruiseto leadRenée Zellwegerand not to Hunt. Instead, Hunt was playing Zellweger’s sister and support system inJerry Maguire. The comforting presence that Bonnie Hunt displayed in these rom-coms easily helped her flex her dramatic muscles as “the wife” trope inRandom HeartsandThe Green Mile, as well as let loose in familycomedies likeJumanjiandCheaper by the Dozen. Hunt has truly taken advantage of her likability in her voiceover career, which includes mega-franchisesCarsandToy Story.
Rent on Amazon
6Christina Applegate
Quirky Best Friend: Courtney Rockcliffe in ‘The Sweetest Thing’ (2002)
WhileChristina Applegatebegan her careeras the blonde bombshell type, she provided some great quirky best friend characters in the early 2000s. One of her best BFF roles wasCourtney in the Cameron Diaz-ledThe Sweetest Thing. Providing both thoughtful insight and gross-out humor, Courtney is the type of character thatshould 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 toGwyneth PaltrowinView from the Top, in which she was free to play up her sassiness; she later tapped back into this mode inBad Moms. In 2010’sGoing the Distanceshe played Corinne, a more grounded best friend, and sister toDrew 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.
The Sweetest Thing
Watch on Prime Video
5Leslie Mann
Quirky Best Friend: Debbie in ‘Knocked Up’ (2007)
Leslie Mannisquirky. 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 cartoonishGeorge of the Jungle, but her supporting role inBig Daddyshowed just how funny and sassy she could be. Mann went head-to-head withAdam Sandleras his love interest’s disapproving sister, leading to a small but memorable gig as a very drunk clubgoer inThe 40-Year-Old Virgin.
Married to comedy legendJudd 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 inKnocked 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 andMann in one of her best films.
Knocked Up
Watch on Max
4Joan Cusack
Quirky Best Friend: Cyn in ‘Working Girl’ (1988)
After a brief 17-episode run onSaturday Night Live,Joan Cusackfound herself as an in-demand quirky best friend. 1988’sWorking Girlfeatured Cusack’s Cyn stealing the show fromMelanie Griffth’s more traditional and conservative Tess. After Tess finds out about two betrayals (her boyfriend and her boss), Cynplays 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 likeNine Months,Two Much,Mr. Wrong,Grosse Pointe Blank, andA Smile Like Yours. Not only that, but she also took a backseat to the romance betweenRichard GereandJulia RobertsinRunaway Bride, and Kate Hudson androm-com kingJohn CorbettinRaising Helen. And when this bridesmaid finally gets to be a bride as the betrothed inIn & Out, her intended groom (played byKevin Kline) comes out as gay.
3Rebel Wilson
Quirky Best Friend: Fat Amy in ‘Pitch Perfect’ (2012)
In 2011, Australian comedianRebel Wilsongot her breakout gig in the U.S. inBridesmaids. She made such a splash in her brief role that she landed a supporting gig in the super-successfulPitch Perfectfranchise. Using the moniker “Fat Amy,” Wilson’s character is confident, crass, and over-the-top – but she’s onlyoneof 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 inHow to Be Single. StarringDakota Johnson, Leslie Mann, andAlison 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 thequirky best friend inIsn’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.
Pitch Perfect
2Kathryn Hahn
Quirky Best Friend: Michelle Rueben in ‘How to Lose a Guy in 10 Days’ (2003)
Kathryn Hahnhas been stealing scenes from leading ladies since her breakout role in 2003’sHow 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 titansKate HudsonandMatthew McConaughey. Viewers could see themselves having a friend like her – or relating directly to her; not everyone can be Hudson. Hahn followed this up withWin a Date with Tad Hamilton, playing second fiddle toKate Bosworth, andThe Holiday, in which she took a backseat to both Cameron Diaz andKate Winslet.
Hahn’s over-the-top comedic work inStep Brothersproved that she could stand toe-to-toe withWill FerrellandJohn C. Reilly, but it wasn’t untilBad MomsandA Bad Moms Christmasthat 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 madeviewers want to party with her.Now, she is stepping out of the shadows and starring in moving, emotional series likeMrs. FletcherandTiny Beautiful Things, as well as headlining her ownMCU spin-off series,Agatha: Darkhold Diaries, fromWandaVision.
How to Lose A Guy In 10 Days
1Judy Greer
Quirky Best Friend: Lucy Wyman in ‘13 Going on 30’ (2004)
In the 2000s,Judy Greerwas everyone’s quirky best friend. She supported leading ladies likeJennifer LopezinThe Wedding Planner,Jennifer Garnerin13 Going on 30, and Katherine Heigl in27 Dresses. The irony of playing the quirky best friend (again) to a perpetual bridesmaid in27 Dresseswas also not lost on Greer. Using her deadpan delivery to excellent effect, Greerranges 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 filmographyas the quirky best friend. When asked why she often gets typecast in these kinds of roles,she said to Conan O’Brienthat 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 bookandmade a short filmthat embrace and poke fun at her onscreen quirky best friend persona. In another interview,Judy Greer explainedthat 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 thenewHalloweenfilms,Jurassic World, andAnt-Man and the Wasp.
