The best romantic comedies

By Megan Riedlinger 5:12am PDT, Oct 5, 2021

If there's one type of film that continues to thrive with every passing decade, it's the romantic comedy! Join Wonderwall.com as we round up our favorite rom-coms of all time in honor of the 20th anniversary of the release of 2001's "Serendipity" on Oct. 5, 2021. The film chronicles the experiences of two people — Kate Beckinsale's Sarah and John Cusack's Jonathan — who, after meeting one fateful night, call upon destiny to bring them back together. Ten years and a ton of miles later, they find themselves back in New York City and consistently missing one another by mere moments. Looking for signs of each other in books and on paper bills, Sara and Jonathan wonder if their connection is something that will ever be reignited. Cheesy in the best way possible, "Serendipity" completely leans into the predictability of romantic comedies. Sometimes, all you want is to watch a film with a guaranteed happy ending!

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Led by "Lizzie McGuire" star Hilary Duff, 2004's "A Cinderella Story" tells a modernized version of the classic fairytale. Following her father's tragic death during an earthquake when she was a little girl, social outcast Sam Montgomery is forced to live under her evil, gold-digging stepmother's (Jennifer Coolidge) tyranny. Even with a strict schedule that revolves around her waitressing job at the diner previously owned by her dad, Sam constantly has to do chores around the house, so there's hardly any time for her to enjoy being a teenager. A silver lining in her otherwise bleak existence? The anonymous, online relationship she has with "Nomad," who turns out to be Austin Ames (Chad Michael Murray), the most popular guy in school! Can their connection overcome their disparate social rankings? The film also includes one of the most iconic rom-com moments: When Sam tells Austin that waiting for him is "like waiting for rain in this drought: useless and disappointing." So good.

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We love an iconic line, and "Notting Hill" certainly delivered in that department when it came out in 1999. It was a classic tale of boy meets girl, with Hugh Grant taking the lead as quirky yet irresistible bookstore owner William Thacker and Julia Roberts playing the "girl, standing in front of a boy, asking him to love her" — aka Anna Scott, a super-famous Hollywood actress transplanted to Notting Hill, London. The unlikely duo fall in love after Anna unexpectedly steps into his bookstore and their love story culminates in the most romantic press conference of all time, with William pretending to be a reporter to win back the love of his life.

Inspired by Shakespeare's "Twelfth Night," 2006's "She's the Man" follows former teen queen Amanda Bynes as Viola Hastings, a teenage girl who poses as her twin brother, Sebastian, in an effort to make his boarding school's all-guys soccer team. At Illyria Prep, Viola (as Sebastian) is roommates with the soccer team's hunky captain, Duke Orsino (Channing Tatum). The two strike up a deal: Duke will coach Sebastian leading up to soccer tryouts if Sebastian puts in a good word with his lab partner, Olivia Lennox (Laura Ramsey), on whom Duke has a major crush. As Viola's secret feelings for Duke amplify, so does Olivia's crush on Sebastian… who is actually Viola. Meanwhile, Sebastian's ex-girlfriend Monique Valentine (Alex Breckenridge) frantically tries to discern his whereabouts. Boasting a stellar soundtrack that includes early '00s bops like "Move Along" by The All-American Rejects and a charismatic cast, this rom-com is a total delight.

"Forgetting Sarah Marshall" stars Jason Segel as Peter Bretter, a struggling composer who lacks the motivation to continue bringing his dreams to fruition. Fed up with her boyfriend's seemingly unending rut, television star Sarah Marshall (Kristen Bell) cheats on and then dumps him. Devastated, Peter travels to Hawaii in a final effort to win her back — only to realize she's vacationing with her new rock star beau, Aldous Snow (Russell Brand). Amidst his struggle to put the relationship behind him, Peter meets Rachel Jansen (Mila Kunis), the resort's receptionist, and they soon form a connection. This rom-com — which marks yet another collaboration between Jason (who also wrote the script) and filmmaker Judd Apatow (who produced) — is as hilarious as it is heartfelt. Also, Kristen shines as the titular, terrible ex!

The best rom-com of all time just might be this true classic — "When Harry Met Sally." The 1989 Rob Reiner film tells the age-old tale of friends turning into something more when Harry (Billy Crystal) falls for Sally (Meg Ryan) while simultaneously portraying things in a painfully realistic fashion with dashes of hilarity thrown in. From iconic scenes like the one in the deli and that perfect New Year's Eve kiss, this Nora Ephron-penned dream of a romantic comedy stands the test of time. It's a textbook-perfect example of the genre.

"Never Been Kissed," the flick that gave naive reporter Josie Geller (played by the always adorable Drew Barrymore) a second chance at high school when she went undercover for an assignment. What followed was a sweet romance between Josie and her English teacher, Sam (played by Michael Vartan), and one of the most momentous kisses — on a baseball field — in movie history.

"Pretty Woman" is a classic for the ages. Lady of the night Vivian (Julia Roberts, in her most iconic role) gets swept into a real life fairy tale in Beverly Hills after wealthy businessman Edward (Richard Gere) picks her up one night. Besides spawning one of the best shopping scenes in movie history ("Big mistake! Huge!"), the film also includes a happy ending that's not all about a damsel in distress. Vivian "rescues" Edward back after the two fall in love and get ready to ride into the sunset and start a new life together.

Imagine falling in love with a seemingly normal guy only to discover that he's from one of the most famous and filthy rich families in Singapore. That's the premise of "Crazy Rich Asians," which follows the romance of American professor Rachel Chu (Constance Wu) and secret rich guy Nick Young (hunky Henry Golding in his first acting role). Besides offering up an amazing makeover scene filled with couture, this film shows that sometimes the heroine doesn't have to give up anything to get the guy. It was not only the top rom-com of summer 2018 but the highest grossing romantic comedy of the last decade.

"Those who can't wed, plan!" In 2001's "The Wedding Planner," Jennifer Lopez's unlucky in love wedding planner Mary Fiore falls for pediatrician Eddie (played by resident rom-com hunk Matthew McConaughey) after he saves her life, only to later discover he's actually one of her clients who's engaged to be married. Hilarity ensues after this ironic twist of fate as Mary battles her feelings for Eddie while dodging the affections of an equally hunky suitor, family friend Massimo (played by Justin Chambers). In the end, it's all too obvious that Mary and Eddie are made for one another, and the two reunite at the scene of their first date — an outdoor movie in the park — and presumably live happily ever after after eating only the brown M&Ms together.

In the opening moments of this film, we're warned that this isn't a love story. Starring Joseph Gordon-Levitt and Zooey Deschanel as Tom Hansen and Summer Finn, 2009's "500 Days of Summer" is one of the most celebrated indie films of the decade. Told nonlinearly, the story follows Tom, an unhappy writer at a greeting card company as he recalls his failed relationship with his co-worker, Summer. The film, which was praised for its script and unique storytelling style, earned two Golden Globe nominations (for best movie musical or comedy and best actor for Joseph). Incredible moments include Tom's "morning after" dance sequence to Hall and Oates' "You Make My Dreams Come True" and that devastating expectation vs. reality scene.

Not many rom-coms clean up at the Oscars, but 1977's "Annie Hall" scored the highly coveted best picture trophy thanks to its innovative take on the genre. Woody Allen stars as comedian Alvy, who happens to be falling for an aspiring singer, Annie (played perfectly by Diane Keaton, who also took home a best actress Oscar that year). Diane once revealed to CBS News that the character was actually based on an "idealized version" of her real self, likely due to Woody and Diane's romantic history off screen. The title character's name was even inspired by Diane, whose nickname was Annie and real last name is Hall.

Sandra Bullock perfected the rom-com early in her career with flicks like "Love Potion No. 9" and "While You Were Sleeping," but it's her film "The Proposal" that earned itself a spot on this list. This love story saw her working as Ryan Reynolds' character's boss, a woman with a stellar career in America who finds herself facing deportation back to Canada — until she comes up with a work-around: marriage. Ryan, her assistant, is promised a promotion if he weds her, so the two enter into an arrangement and even get their families involved. Aside from Sandra and Ryan's chemistry, Betty White steals the show as Sandra's character's grandma.

1987 gave us "The Princess Bride," which straddled multiple genres with fantasy elements and action scenes but was ultimately a romantic comedy at heart. The flick follows Buttercup (Robin Wright) and Westley (Cary Elwes) as they make it through the Cliffs of Insanity, the Fire Swamp and nearly meet their end while falling in love along the way.

Audiences adored "My Big Fat Greek Wedding" when it hit theaters in 2002. This darling flick features a lovable, dutiful Greek daughter, Toula (Nia Vardalos), who still happens to live at home and work at her parents' restaurant. When non-Greek customer Ian Miller (John Corbett) stops by, Toula takes notice and develops a crush. It's not until she goes through an adorable makeover — which includes taking computer classes and working on her inner self, as well as getting a new wardrobe and ditching her glasses for contacts — that he takes notice as she works at her aunt's travel agency. The two fall in love and the rest is one big, fat, traditional Greek wedding.

Not all rom-coms feature impossibly glamorous leading ladies. Enter "Bridget Jones's Diary," the 2001 flick about a very single 32-year-old British woman, Bridget Jones (played by Renee Zellweger), and her quests to find love. Suddenly, she finds herself smack dab in the middle of two love interests, boss Daniel Cleaver (Hugh Grant) and family friend Mark Darcy (Colin Firth). This romantic comedy was so adored by audiences that it spawned two more films over the next decade and a half — "Bridget Jones: The Edge of Reason" in 2004 and "Bridget Jones's Baby" in 2016.

"Legally Blonde" was not just an incredible rom-com. It also gave us a stellar role model in the form of Reese Witherspoon's delightfully determined Elle Woods. The 2001 film followed the not-dumb blonde's sparkly pink path to Harvard Law School. Though the journey originally started as a way to stay close to her ex-boyfriend, Warner Huntington III (played by Matthew Davis), Elle quickly found herself thriving while making unlikely allies at the esteemed law school. And though the romance portion isn't as integral as the tale of Elle overcoming stereotypes and proving herself, she still found a beau in the form of sweet and supportive lawyer Emmett (played by Luke Wilson) who suited her much better.

Even if you haven't seen the movie, you know the move — the boombox over the head. We have "Say Anything" to thank for that, specifically John Cusack's character, Lloyd Dobler. This take on high school love was a pleasant surprise in 1989, with underachiever Lloyd setting out to woo the brilliant and beautiful class valedictorian Diane Court (played by Ione Skye). Their unlikely romance results in that classic scene in which Lloyd blasts "In Your Eyes" by Peter Gabriel under Diane's bedroom window before their romance eventually heads to England.

No rom-com embraces the genre quite like "How To Lose A Guy in 10 Days." The flick features classic romantic comedy leads Matthew McConaughey as Benjamin Barry and Kate Hudson as Andie Anderson, two characters who of course have quintessential rom-com jobs. Andie writes for a women's magazine and is assigned to report an article titled "How to Lose a Guy in 10 Days," while Benjamin is an ad executive who's so eager to head a new diamond campaign that he bets his boss he can make any woman fall in love with him. Add a squeal-inducing soundtrack (Keith Urban's "Somebody Like You," anyone?) and a rush-to-the-airport-to-win-her-back trope and you've got one of the best rom-coms of the bunch.

We're sorely in need of more teen rom-coms, especially if they're like 2010's "Easy A." This film helped rocket Emma Stone to stardom thanks to her flawless portrayal of outcast Olive Penderghast, a modern-day Hester Prynne from "The Scarlet Letter." The high school student lies about losing her virginity, only to develop a certain reputation — and then use it for good by helping other kids get popular. Yep, by accepting gift cards in exchange for corroborating other students' hookup stories, Olive turns into quite the entrepreneur while actually finding love with fellow outsider Todd (played by Penn Badgley).

It's every teenage girl's nightmare: to have her birthday forgotten by virtually everyone in her life. "Sixteen Candles" — John Hughes' 1984 coming-of-age romantic comedy — explores what happens when Sam Baker's (Molly Ringwald) 16th birthday is overshadowed by her older sister's impending wedding. The film features all the major components of an iconic teen rom-com: a gorgeous crush (Michael Schoeffling), a wacky family and a ton of existential dread. This one's a classic.

Tom Hanks stars in Nora Ephron's 1993 classic "Sleepless in Seattle" as Sam, a widower who struggles to discuss his feelings. In an effort to make his father open up and possibly even find a new wife, young Jonah (Ross Malinger) calls a radio station to force his dad to speak. It just so happens that Baltimore reporter Annie Reed (Meg Ryan) is listening to the show and instantly becomes enamored with this mystery man. Set in Seattle and Baltimore, "Sleepless in Seattle" tells a seriously romantic story about two people who finally meet at the right place and the right time. The Empire State Building has never seemed more romantic.

"13 Going on 30" helped solidify Jennifer Garner's America's sweetheart status, and for good reason. The feel-good rom-com from 2004 showed Jen's character, Jenna Rink, navigating life as a 13-year-old girl trapped in a 30-year-old woman's body, resulting in laughs and an adorable time-traveling romance with childhood best friend Matt (played by Mark Ruffalo).

What's better than a rom-com inspired by a real-life love story? That's exactly what "The Big Sick" is. It's inspired by comedian Kumail Nanjiani's real-life romance with wife Emily V. Gordon. The couple wrote the script for the 2017 flick, basing it on their unconventional courtship, which involved Emily falling into a coma and Kumail staying right by her hospital bedside despite it being very early in their relationship. Kumail played himself while Zoe Kazan filled in for Emily in this heartwarming tale that scored a best original screenplay Oscar nomination.

"It's Complicated" earns a spot on the list for its, well, complicated portrayal of love after divorce. Jane Adler (played by Meryl Streep) is torn between her hunky ex-husband, Jake (Alec Baldwin), and the sweet architect working on her home's remodel, Adam (Steve Martin). Like all Nancy Meyers movies, this one left us as enamored of the main character's kitchen and dreamy day job (she's a bakery owner) as we were of her romantic choices.

Next up is the romantic comedy with the most stylish and eternally cool lead of all time — "Breakfast at Tiffany's." Though Audrey Hepburn starred in many a rom-com, it's this classic tale that nabs a spot on the list. Her portrayal of Holly Golightly, the whimsical New Yorker with a dreamy breakfast routine and iconic wardrobe, made us fall in love despite the fact that she ditched her cat in the rain. Her reluctant romance with Paul Varjak (George Peppard) kept us riveted.

As if "Clueless" wouldn't be on this list! This classic teen rom-com features the fashionable, lovable and, well, clueless Cher Horowitz (Alicia Silverstone) who helps others find love while failing miserably herself. She eventually realizes her perfect match has been right under her nose the whole time — her stepbrother Josh (the ageless Paul Rudd). The 1995 flick is loosely based on Jane Austen's "Emma," though it delivers a perfectly '90s upgrade.

While it might solicit eye rolls nowadays for its predictable story, there was a time in which "She's All That" was considered original! The 1999 teen romantic comedy stars Freddie Prinze Jr. as Zack Siler, the student body president and most popular (and desired) guy in high school. After he's dumped by Taylor Vaughan (Jodi Lyn O'Keefe), his Queen Bee girlfriend who cheats on him with "Real World" reality star Brock Hudson (Matthew Lillard), Zach boasts that he can turn any girl into the prom queen. When his diabolical best friend Dean (Paul Walker) calls his bluff, Zack is tasked with having to turn Laney Boggs (Rachael Leigh Cook), an unapproachable and unpopular art kid, from freak to chic. From Laney walking down the steps to debut her new look as Sixpence None the Richer's "Kiss Me" plays to her incredible "Am I a bet?!" line, "She's All That" is a '90s rom-com full of iconic moments.

It's quite the dream — or nightmare — come true for an awkward teen: Finding out she's a real-life princess and heir to a country's throne! Starring Anne Hathaway as San Francisco teen Mia Thermopolis, 2001's "The Princess Diaries" charts her life as she goes from social outcast to prim-and-proper princess. With the help of her grandmother, Queen Clarisse Renaldi (Julie Andrews) of Genovia, Mia learns what it takes to be a royal, all while trying to maintain some semblance of normalcy as she attends high school. With her newfound title comes unforeseen popularity — and when Mia's longtime crush Josh (Erik von Detten) begins paying her attention, she believes life can't get any better. The more important burgeoning love story, though? The one between Mia and her best friend's brother, Michael (Robert Schwartzman). "You saw me when I was invisible." Swoon!

We'll never forget this line: "But mostly I hate the way I don't hate you, not even close, not even a little bit… not even at all!" When "10 Things I Hate About You" debuted in 1999, it was an instant hit with moviegoers. The updated retelling of Shakespeare's "The Taming of the Shrew" stars Julia Stiles and Heath Ledger as Kat Stratford and Patrick Verona, two social outcasts who are brought together in an elaborate ploy spearheaded by affluent jerk Joey Donner (Andrew Keegan) so he can get with Kat's younger sister, Bianca (Larisa Oleynik). Of course, what starts off as a ruse that's strictly about the money turns into something much more complicated when Patrick begins falling for Kat! From Kat's snarky attitude to Patrick's grand gesture — belting out "Can't Take My Eyes Off You" by Frankie Valli — this rom-com remains a treat to rewatch.