It’s about how love really is sometimes, which can be romantic in its own right. It’s a fantastic romantic comedy, and won two Academy Awards for acting in recent years (something really rare to happens with comedy movies), and has a good tomatometer – 86 per cent -, and i am upset, they forgot THIS film, but put Enough Said and Treinwreck, which is not that great. As much as we commiserate, this is ultimately Hugh Grant’s movie. As much of a coming-of-age story as a rom-com (Muriel may be in her 20s, but she has much growing up to do), this film does a brilliant job of cutting the legs out from underneath our expectations by giving us exactly what we’ve always wanted and tying us up in the strings attached. The 33 Best Romantic Comedies of All Time. Despite its memorably demonstrative, over-the-top lines, like “You complete me” and “Show me the money,” this is ultimately a movie about how people really fall in love. ...to make your rom-com collection a little less straight and narrow: Directed by Jamie Babbit, this dark comedy centers around religious high-school cheerleader Megan (Natasha Lyonne) being sent away to “straight camp,” where the staff attempts to turn her and her fellow queer teens toward the Lord. When Winslet’s heartbroken Iris leaves behind her English cottage for Diaz’s sunny Los Angeles paradise, she finds a new lease on life (and a new crush, played by Jack Black). After the slap-happy, very silly, and very male comedies of the late ’70s and early ’80s (think Animal House, Porky’s, and Revenge of the Nerds), and alongside epic big-budget projects like Ghostbusters and the original Indiana Jones, Brooks continued to redefine what rom-coms could be with this sprawling, occasionally dramatic, but never self-serious workplace comedy. You end up cheering not just for her romance, but also for an entire insurgency. Originally cynical about all things pageant-related, Grace ends up building real friendships amid all the hairspray and lipstick; and, of course, she builds a little more than a friendship with her coworker, played by Benjamin Bratt. As for Diaz, she learns to shed her chi-chi Angeleno expectations and embrace rural life, as well as a handsome Englishman played by Jude Law. So glad to see What’s Up, Doc on this list. There’s a question that lingers throughout most of Harold and Maude—the story of a death-obsessed young man (he enjoys driving a hearse, attending funerals, and faking his suicide) who falls for a much, much older woman—are these two going to get it on? It’s an incredibly touching, difficult story, told mostly in flashback, that involves Oliver coming to grips with his father’s past, his parents’ relationship, his own choices, and his art. And that was in a year when the Rolling Stones released Some Girls and Bruce Springsteen dropped Darkness on the Edge of Town. And it’s too busy diving into the angsty, all-consuming, awkward challenge that is young love, as embodied by consummate underdog Lloyd Dobler and his attempts to woo the beautiful valedictorian Diane Court. ...to make your arguments a little sweeter: Here’s how cute rom-coms were in the 1930s: The entire plot rests on a dog burying a bone of a brontosaurus. In the mid-to-late 1970s, New York was a bit of a cesspool: Crime was out of control, repeated requests for federal aid were denied, and the city was on the edge of bankruptcy. Max Fischer (Jason Schwartzman) is a scholarship student at a private school. Same with top 10—and 5. Yes, it was a different era, but this detail can be difficult to ignore. I just saw a movie that should make this list in the future. It’s a panacea for the reasons we go to the movies. The princess screams—Hepburn was apparently not acting here—and then recovers. Like Bring It On, and unlike most films, especially teen films, this one is female-focused. We. TV … It’s for this reason we need to apologize in advance: A number of your favorite romantic comedies will not be on this list. 60 of the best funny romantic comedies to watch and stream, including Wedding Crashers, Forgetting Sarah Marshall, Plus One, and Always Be My Maybe. Instead, we have movies that are actually fun to watch, like Shakespeare in Love, and this one, a teen-ready take on The Taming of the Shrew. May 14, 2020 Everett Getty Images. Bonus: Keanu Reeves appears as a hunky doctor. This is Wes Anderson’s most completely stylish movie, and perhaps his best, made before stylized fuckery got in the way of things like writing. The Main Line has never been so well represented. ...to make you plan a destination wedding in Singapore: Based on the novel of the same name by Kevin Kwan, this film takes a deep dive into the splashy, sparkling lives of Singapore’s elite, with the story of Rachel (Constance Wu), who falls in love with Nick (Henry Golding) before learning that his family, headed by terrifying matriarch Eleanor (Michelle Yeoh), is among the richest in Singapore. Read full article. All rights reserved. What’s left to say about the 1990 tale of the beautiful, charming sex worker and the Wall Street corporate raider who meet and fall in love? Despite the over-the-top locker-room gags, the movie has virtually no sex and manages to emerge as hilarious, sweet, and satisfying. With barely a word, only whirrs, between them, EVE and WALL-E convincingly fall in love. Forget Finding Nemo, this is writer-director Andrew Stanton’s Pixar masterpiece. Menu. The way she pulls at her dress. It’s madcap and zany but also profoundly funny, with insights aplenty—it sends up television, sexism, and New York society—and performances that were Oscar-worthy (Lange’s in particular—of Tootsie’s 10 Oscar nominations, she’s the only one who walked away with a statue). The Tomatometer, just like the heart, does not deceive. The story has a classic but important lesson to share: First impressions aren’t everything (and a fashion-related takeaway—never judge a man by his Christmas sweater). An advance copy just came out and he's the best man at his friend's wedding (where everyone in said book will be in attendance). Release Calendar DVD & Blu-ray Releases Top Rated Movies Most Popular Movies Browse Movies by Genre Top Box Office Showtimes & Tickets Showtimes & Tickets In Theaters Coming Soon Coming Soon Movie News India Movie Spotlight. In short: Murphy plays the prince of a fictional African nation who is unsure about his arranged marriage, and so heads to what he suspects will be greener pastures in search of his queen. The site uses an algorithm for their rankings that rates some critics' positive reviews as more significant than others', so the movies here aren't just ranked by overall percentage. There are few actors who can go toe-to-toe with Jack Nicholson. This is what we call a screwball comedy. Simultaneously, at a time when every other joke on Friends involved gay panic, he was portraying three-dimensional concepts of lesbian identity. Right, sleep with Mr. After all, that’s the message from Pretty Woman, right? And this is his best work. ©Buena Vista Pictures/Courtesy Everett Collection, ©TriStar Pictures/Courtesy Everett Collection, ©Columbia Pictures/Courtesy Everett Collection, Entertainment Pictures / Alamy Stock Photo, ©Focus Features/Courtesy Everett Collection, ©New Line Cinema/Courtesy Everett Collection, ©Orion Pictures Corp/Courtesy Everett Collection, ©United Artists/Courtesy Everett Collection, Photo: Courtesy of © 20th Century Fox Film Corp./Everett Collection, ©Sony Pictures/Courtesy Everett Collection, ©Walt Disney Co./Courtesy Everett Collection, ©GramercyPictures/Courtesy Everett Collection, Diane Keaton and Jack Nicholson–fronted romp, bragged openly about grabbing women “by the pussy”. And in our most recent major update, we’ve added the latest and greatest, including Charlize Theron’s first dip into the genre (Long Shot), indie darlings (Plus One), and the farcical (Isn’t It Romantic). They talk about them differently than other movies, and they like to talk about them a lot. They struggle through misunderstandings, language barriers, cultural clashes, encounters with Marion's many ex-boyfriends, and her unruly parents (played by Delpy's real-life mother and father, actors Marie Pillet and Albert Delpy), and barely come out the other side. The year is important, because as the film’s title suggests, this movie is as much about New York as it is about the lovers who collide inside of it (Allen’s character, Isaac, begins the film dating the high schooler, but leaves her for his friend’s mistress, played by Diane Keaton). As the pair make their way through Manhattan—with visits from Jerry Seinfeld, radio hosts Opie and Anthony, Whoopi Goldberg, and a fantastic supporting job from the ageless Gabrielle Union, playing a reality TV starlet—we can’t help but get on board with their journey. All of it. Keep in mind, it’s directed by Hal Ashby, the king of thoughtful, offbeat romances, and was both written by and featured, Warren Beatty, a major voice of the Hollywood Left in the 1970s. RELATED: The 10 Best Romantic Comedies of All Time Like many of the films on this list, Lost in Translation takes place in a bourgeois universe, where the greatest thing at risk is someone’s heart or future emotional happiness, but few films have so effectively crystalized the alienation of both travel and marriage as well as the difficulties of postcollegiate, and then midlife, malaise. ...remind you that life doesn’t always go as planned, but sometimes that’s okay: Life’s not perfect, but it can be most endearing— that’s the takeaway, anyway, from Jason Reitman’s nuanced teen comedy Juno. October 29, 2019. The ’50s nostalgia of the 1970s culminated with this unreal musical about the return to high school for summer lovers Danny Zuko (John Travolta) and Sandy Olsson (Olivia Newton-John). Best Romantic Comedies A quick note on criteria. Subscribe to our newsletter and get more features, news, and guides in your inbox every week. These skirts know what’s up, and that’s what makes us interested, and invested, in their outcomes. A quiet suitor in love with the new bride (Knightley) of his best bud (Chiwetel Ejiofor), who is apparently one of three people of color in London? The 15 Best Romantic Comedies of All Time: From Annie Hall to The Wedding Singer. Those things aren’t on our minds when we watch this movie (barring an early scene discussing methods of birth control); we think about stomping divots and Richard Gere conquering his fear of heights. The question this rom-com dares ask is this: In all this wedding madness, can you be the odd man out and still be happy? RELATED: The 30 Best Romantic Movies on Netflix That You Can Stream Right Now. The central question of whether love can conquer money is almost outshone by the film’s dazzling surroundings as well as Rachel's nouveau riche friends, played perfectly by Awkwafina and Ken Jeong. There’s something almost quaint about Norah’s search for her orgasm. The material on this site may not be reproduced, distributed, transmitted, cached or otherwise used, except with the prior written permission of Condé Nast. This movie, from director Cameron Crowe (and produced by James L. Brooks), is far too sophisticated for such a middling finale. The reason we can safely call this a rom-com is that, while it doesn’t exactly pass the Bechdel test with flying colors, the objects of the guys’ affections are far from just objects. Ad Choices. Demme’s alchemy here is to infuse the trope with unpredictability. We hope you love them. The brilliant and surprising Julie Delpy writes, directs, and stars as Marion, a young Frenchwoman who has brought her American boyfriend Jack (Adam Goldberg) to her hometown en route from a trip to Venice. Then we dabbled in 21st century raunch (Knocked Up) and twee ((500) Days of Summer), leading into our current era of new voices declaring that they too are entitled to their own messy relationship stories (The Big Sick, Crazy Rich Asians). A little LOL, a lot of awww, all classics. Sandler and Barrymore’s chemistry is off the charts, and this film—not Mad Love, sorry—established the actress as rom-com gold (see Never Been Kissed, 50 First Dates, and Fever Pitch). Harold and Maude are separated by approximately 60 years; for the movie to hit home, for us to believe that love is truly about what we share, not what we look like or other aesthetic values, we have to believe a genuine attraction has formed. “Is this a kissing book?” Fred Savage’s little boy asks his grandfather, at his bedside to read him The Princess Bride when he’s home sick from school. Because often a three-hour production: (1) is rarely funny, and (2) doesn’t really fit into a modern romantic comedy structure. So he does what any rational man would do: He dresses as an entirely different person—an older woman who goes by the name of Tootsie—and lands a role on a soap opera where he becomes a sensation. For our list of the 200 best romantic comedies of all time, we searched high and low throughout movie history for every permutation of (hilarious) courtship and love captured on camera. How can we not, with this ensemble cast of British romance all-stars (Hugh Grant, Emma Thompson, Liam Neeson, Colin Firth, and Keira Knightley, among others)? The prime minister (Grant) falling for a junior staff member? And a little Andie MacDowell’s movie. There was never any doubt that Scarlett Johansson was going to be a megastar, but Sofia Coppola’s movie—about the lonely wife of a photographer who befriends an over-the-hill movie star (Bill Murray) while visiting Tokyo—is what made the world stand up and realize we were dealing with a serious actor. Maybe it’s the best for a certain time period. In Ben Stiller’s feature directorial debut, he also plays a TV executive whose budding romance with Lelaina and interest in her work brings the real world crashing into their postcollegiate hipster existence. Were doorways made wider in the 1980s? It’s hard for current viewers to understand just how big John Travolta was at the time; the year this film bowed, 1978, the two top-selling albums were the soundtracks to Saturday Night Fever (another Travolta film) and this one. ...to provide you with all the J. In 1998 this film competed with Saving Private Ryan, Elizabeth, and Life Is Beautiful for best picture and managed to come out with the Oscar. The latest fashion news, beauty coverage, celebrity style, fashion week updates, culture reviews, and videos on Vogue.com. Like this? She fell down in front of the boss she has a crush on while carrying many things! A definitive comment on the best romantic comedies ever made. Ready to dive into the sea of love? Finding the right one, falling in love, and getting married? Her spins. In that light, IndieWire’s list of the 50 Best Romantic Comedies of All Time is more of a start than a final statement; it’s a living document that we’ll change up and add to as time goes by. They have goals of their own we’re brought on board with. Your uncle or cube-mate might say, “That’s stupid. And it is! Right (by having our hero, a struggling comedian—played by the irrepressibly honest and infinitely endearing Jenny Slate—get drunk with Mr. It sounds like rough going, but John Krasinski is there to provide comic relief. The comedy keeps us on the edge of our seats by compounding the will-they-won’t-they question with sudden breaks into violence, threats, or chase. Unfortunately for them, that doesn’t quite work out, as Megan falls hard for her fellow female camper Graham (Clea Duvall). Similarly, the Pink Ladies, a popular clique headed by Rizzo (Stockard Channing), deliver their wiseacre lines with a fair dose of irony. Like Roman Holiday before it, this is a film rooted in our society’s placement of, and expectations for, certain figures (a celebrity and a princess, respectively). However, we know that you can never go wrong with romantic comedies. And because we want you feeling red, and not seeing red, we want to prepare you for some of the relatively low placements for beloved classics like Pretty Woman, Love Actually, and Sleepless in Seattle. Kate Winslet and Cameron Diaz trading lives? Murray gets stuck there, not just in a snowstorm, mind you, but in a continuous loop, where no matter what he does—including suicide—he wakes up in the same hotel on the same day. For younger viewers—those of us who might not have drunk down the moving magic of Singin’ in the Rain, West Side Story, or Gigi—Damien Chazelle’s La La Land forgives those lapses. What we love about this futuristic tale of a little trash compactor, WALL-E, who falls in love with his technological better, EVE, is the considered environmental, anti-consumerist message that suffuses the dystopian love story. If they do, what happens next? Use of this site constitutes acceptance of our User Agreement (updated as of 1/1/21) and Privacy Policy and Cookie Statement (updated as of 1/1/21) and Your California Privacy Rights. The older man and the younger woman don’t so much meet-cute as crash into each other, picking up each other’s pieces, redeeming each other’s lives as they navigate their surreal setting. Billy Madison and Happy Gilmore are ’90s classics, and The Wedding Singer, his only rom-com from that era (there’s some debate over whether P. T. Anderson’s Punch-Drunk Love, released in 2002, qualifies as such), is a hilarious, touching ode to traditional values. Lesbian conversion? (Not to mention the sexual viability of Williams grads.) ...to unplug from the office (and get your due): The movie that inspired 90 percent of vacation hookup jokes since 1998 (but seriously, we need to talk about Taye Diggs in a puka shell necklace; the man can make anything look good). Their love. ...to satiate your soft side (and make you hungry for kimchi jjigae): Ali Wong and Randall Park have ridiculously good chemistry in this 2019 film about a pair of childhood best friends who become awkward teenage lovers. it had a 100% on the tomatometer up until about 2 years ago when a couple “new” critics ruined the perfect score. No one prodded existentialism (especially in films deemed “romantic”) like director Hal Ashby, and Harold and Maude is no exception. There is no “best” romantic comedy. Copyright © 2018 Fandango. ... after you watch them play the ideal versions of Beatrice and Benedick in Branagh's adaptation of one of Shakespeare's best romantic comedies. (2011) Bridesmaids (2011) Beginners (2010) Easy-A (2010) Knocked Up (2007) The 40 Year Old … The guy ruled the ’80s and made some of the era’s great comedies—Trading Places, Beverly Hills Cop, 48 Hrs.—but this is really the only one where the romance narrative rules supreme. Silver Linings Playbook and THE PHILADELPHIA STORY are my faves. This movie should be watched by every college student on the planet. The girls aren’t just out for the boys, they’re out for themselves—as disappointingly rare in a rom-com as it is in a teen comedy, and the reason we love this one. There was plenty to find in the John Hughes, teen-driven era (Say Anything…, Pretty in Pink), and the bubbly ’90s decade that followed (Groundhog Day, Four Weddings and a Funeral, While You Were Sleeping). For the next time nothing but a good rom-com will do, we ranked the 65 best and most heartwarming rom-coms of all time, from old favorites to modern classics. When we set out to rank the best Romantic Comedies of all time, we had to set some ground rules. It may not be easy, but it's highly entertaining to watch them try. But that’s not why we go to the movies. Bonus: This film features one of the best makeover montages of all time, set to “Mustang Sally.”. Dickinson and Hawkeye Star Hailee Steinfeld Relishes Playing Strong-Willed Characters Who ‘Use Their Voice’, 100 Best Movies on HBO Max (January 2021). It’s a window to another time, when marriage meant something different in male-dominated second-generation immigrant families, and the challenges Cher’s character places against the social order are both important and revelatory (she won an Oscar for her efforts). Where’s As Good as it Gets? William Shakespeare's 'A Midsummer Night's Dream', You're Killing Me Susana (Me estás matando Susana), All Studio Ghibli Movies Ranked by Tomatometer, All Hayao Miyazaki Movies, Ranked By Tomatometer. ... sweetest and most romantic comedies of all time. An exhaustive list of the best romantic comedies for any and all occasions, from “When Harry Met Sally” to “Pretty Woman.” And expect to see more international rom-coms, with plenty of additions among Spanish-language (You’re Killing Me Susana, Everybody Loves Somebody) and French cinema (Romantics Anonymous, The Spanish Apartment). Utterly contrived, but utterly charming, this quick, silly, funny film is pabulum superfood for anyone who believes in second chances and true love. Comic books? Rosario Dawson plays a New York Times journalist tasked with interviewing a hugely famous comedian, played by Chris Rock, who is attempting to take his career in a new direction (courtesy of an ill-advised serious film about a Haitian revolutionary). While some people may scoff and sit on their high horse regarding this particular movie genre, I say they’re just absolutely wrong. It’s a comedy that’s as much about accepting the facts of life—be they middle age, the people we can’t have, or the people we don’t want others involved with—as much as it is about a pursuit or any one relationship. If you agree, welcome to the squad. It’s being taken by surprise, taken by a stranger, the discovery of a new side of oneself while falling for someone else. ...to get past that one little (or gigantic) flaw: Cher plays a widowed bookkeeper in Brooklyn Heights confronting her parents’ infidelity (and fallibility) who—whoops!—falls for her fiancé’s younger brother (Nicolas Cage), who sports a prosthetic wooden hand after an accident with a bread slicer. ...to deal with your workplace crush(es): In the mid to late ’80s, there was nothing bigger than TV news and James L. Brooks, and Broadcast News was their meeting ground. This somewhat slept-on rom-com features Bullock as a grumpy, dedicated environmental lawyer who takes a job with Hugh Grant’s massive company in order to ensure the safety of her beloved local community center. Where is Say Anything? If romantic comedies about best friends falling in love is your cup of tea, “When Harry Met Sally…” redefines the meaning of friend zone on both sides of the equation: and how to get out of it. When she makes off with her parents’ savings, reunites with a fellow outcast from her town, and is offered the chance to marry a gorgeous South African swimmer who needs a visa, she can make her dreams come true. But Kevin Smith also managed a somewhat nuanced exploration of friendship and art, as well as of contemporary romantic standards in his rejiggering of the love triangle. This modern-day Cinderella story showcases J. Lo’s acting talents as well as her chemistry with Ralph Fiennes. At the same time, they maintained a storybook sensibility and somehow kept our sympathies with the lovelorn Cher, whose insipidness is overshadowed by her charity, loyalty, and genuine goodwill. It’s a metaphoric yawp for all that a romantic comedy should be. Nick and Norah’s Infinite Playlist (2008). Updated on April 30, 2020, by Richard Keller: Comedy is timeless when it comes to film. But what pushes it above the rest is the utter drive of both Max and Herman, as love and competition gain primacy over every aspect of their lives. Hooking up? ...to remind you of the complexity of female friendship: This soapy delight stars Kate Hudson and Ginnifer Goodwin as Darcy and Rachel, two lifelong best friends with resentment aplenty brewing between them. That said, Beatty’s portrayal of the harried, discursive, libidinous George is irresistible even without context, as is the performance given by a young Goldie Hawn, who illuminates every frame—and perfectly counteracts Beatty—with blonde California light, and a heart-melting, downy innocence. More than anything, it’s a tale of true love, and fantastic as it might be, the adventure that leads the stable boy, Westley, back to his mistress, Buttercup (played by an impossibly beautiful Robin Wright), has left few hearts unmoved and few faces without smiles. It’s something of an epic of the genre, spanning over 10 years of the kind of friendship (between Meg Ryan and Billy Crystal’s characters) where no one can help but ask, “Why aren’t those two together?” Should friends ever sleep together? ...to soothe your Hamptons beach-house cravings: This Diane Keaton and Jack Nicholson–fronted romp is the platonic ideal of a Nancy Meyers movie, featuring beachside scenes, cashmere turtlenecks, and endless amounts of kitchen porn. The best medicine for dark times is a romantic comedy. Based on Truman Capote’s 1958 (harsher) novella of the same name, Breakfast at Tiffany’s—the story of a friendship struck between a rarely employed writer, Paul Varjak, and his neighbor, the naïvely beautiful Golightly, a freewheeling party girl whose lifestyle is paid for by the rich suitors who surround her—is a building block of our Hollywood romantic fantasies. We also expanded our reach in LGBTQ (Edge of Seventeen, Get Real, Life Partners, Saving Face) and African-American films (Top Five, The Best Man). It’s produced by Joseph L. Mankiewicz (writer of All About Eve and Cleopatra), and directed by George Cukor (who made 1954’s A Star Is Born, Justine, and My Fair Lady, and once told Marilyn Monroe, “That will be just fine, darling,” when, about to film a skinny-dipping scene for Something’s Got to Give, she expressed her concern that she only knew how to dog-paddle). The heroes we cheer for. Here are the best romantic comedies of all time, ready to be enjoyed and given their proper respect. One of these is Alexis Dziena, who plays Nick’s very recent ex-girlfriend: She toyed with him and never appreciated the music mixes he made for her (spoiler: Norah loves them). A cynical Pittsburgh weatherman (Bill Murray) is sent to Punxsutawney, Pennsylvania, with his producer, Rita (Andie MacDowell) on a dead-end assignment: to cover Groundhog Day. Director James L. Brooks found a suitable sparring partner with Shirley MacLaine in Terms of Endearment and struck gold again nearly 15 years later with Helen Hunt. Romantic tension builds alongside genuine friendship in Two Weeks Notice, making it the rare rom-com with a happy ending that actually feels earned. The motherless daughter, caring for her father and looking for her prince, is a trope that goes back to fairy tales, but how Alicia Silverstone (who plays our hero, Cher) and writer-director Amy Heckerling contemporized that narrative is what made what could have been a silly teen flick into an instant classic. There are more epic Disney romances (one of them is on this list), but none more thoughtful. ...to reevaluate the nice guy (and the bad boy): Before Jonathan Demme decided to win an Oscar and scare the pants off an entire generation with The Silence of the Lambs, he was an ’80s funnyman. Elephant in the room: Yes, this is Woody Allen pursuing a high school student (a luminous Mariel Hemingway). The story of Grant and his friends attending their friends’ weddings—and one funeral—perfectly captured the romance of nuptials as well as all the stress, commitment, and emotional...what do the British call it?...oh yes, bother that comes with that period in your life where your friends are tying the knot. Essentially slumming it with his best friend (a terrific Arsenio Hall), Murphy’s character finds work at a McDonald’s-type restaurant where he falls in love with the owner’s daughter, a woman who just might fit the bill. Then continue on with open arms into Rotten Tomatoes’ 200 best romantic comedies of all time! RELATED: The 50 Best Romantic Comedies of All Time to Watch With Your Friends. But it’s irresistible. “Did you see that? I have seen all of these and a few would not be on my list at all. Aside from a nonstop ’90s fashion buffet that is Winona’s wardrobe (mom jeans, crop tops, baby doll dresses, cardigans, men’s shirts, blazers), there’s also love and heartbreak, sex, betrayal, Lisa Loeb, Dickies, pizza, and lines like “He’s so cheesy, I can’t watch him without crackers.” What else do we want, really? We mean the films that got nominated for Oscars, feature a variety of A-listers (and a whole lot of Hugh Grant), and made Rotten Tomatoes's list of best romantic comedies of all time. And that’s just one moment! There are some cute turns from youngsters Joseph Gordon-Levitt, Julia Stiles, and Larisa Oleynik, but ask most women, and the performance that sticks out is Heath Ledger’s, whose thuggish Patrick Verona made many of us weak in the knees. Katharine Hepburn, whom the movie was written for, plays a whimsical, adorable socialite who has become besotted with an otherwise engaged (literally and figuratively) paleontologist, played by Cary Grant, and is trying to keep him around so he won’t go marry some pill. Right, get pregnant by Mr. ...to consider what you could have done differently: One of the few rom-coms that comes with both a stamp of approval from your philosophy professor and the Tony reaches of Broadway. ...to make you fall in love with your friends: In what was then a cult hit and is now a piece of ’90s nostalgia catnip, a post–Edward Scissorhands (and post–Johnny Depp) Winona Ryder plays Lelaina, an aspiring documentarian assisting an obnoxious TV host in Houston. By the irrepressibly honest and infinitely endearing Jenny Slate—get drunk with Mr best New culture, style, and stories... As her hot Secret Service crush, played by Marc Blucas—gives this incarnation edge! 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