The 100 Best Romantic Comedies of All Time

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75. Jeffrey (1995)
Director: Christopher Ashley

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Based on a play of the same name, written by Paul Rudnick, this charming and witty little morsel tracks the efforts of its titular character (Stephen Weber) as he attempts, at the peak of the AIDS crisis, to avoid any and all relationships, sexual or otherwise. But when he finally does find a potential partner in the form of a cute HIV+ gent (Michael T. Weiss), Jeffrey’s flimsily built wall protecting him from the world starts to crumble. While it plays some very serious concerns for laughs, the film doesn’t shy away from the bitter reality of how many people had been taken away from the world due to AIDS. It also serves as a reminder of why seeking connection and affection in the faces of such trials is so important. Plus, as with all of Rudnick’s work, the film is filled with sharp, pithy dialogue, handled ably by a winning cast that includes some delightful supporting work from Sir Patrick Stewart, Nathan Lane and future Mad Men cast member Bryan Batt. —Robert Ham


74. 10 Things I Hate About You (1999)
Director: Gil Junger

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Inspired by William Shakespeare’s The Taming of the Shrew, the 1999 teen comedy places Katherina and Petruchio into modern times as feminist Kat and bad boy Patrick, the breakout roles for Julia Stiles and Heath Ledger. (There are more than a few entries on this list drawn either directly or indirectly from the Bard’s comedies—that guy was a legend!) Patrick is initially paid to charm Kat as a part of an elaborate scheme by Cameron (Joseph Gordon-Levitt) to take out her younger sister, Bianca. Ledger wins Kat and the majority of the female population over during his marching band-accompanied stadium performance of Frankie Valli’s “Can’t Take My Eyes Off You.” Though Kat is angered when finding out about the deal that formed her relationship, the so-called shrew can’t stay mad for too long after receiving a sincere apology and brand new guitar from her Australian beau. With the perfect amount of ‘90s nonsense, the film ends with Letter to Cleo equally perfectly performing Cheap Trick’s “I Want You to Want Me” atop the roof of Padua High School. —Stephanie Sharp


73. Roxanne (1987)
Director: Fred Schepisi

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“Because I was afraid of worms, Roxanne! Worms!” Steve Martin’s late-’80s rom-com isn’t just his take on Edmond Rostand’s play, Cyrano de Bergerac , it’s also a funny depiction of what would happen were everyone to conduct their romantic lives as if they were giant games of Telephone. Roxanne is one of those smart comedies that seems to effortlessly balance complex, often serious themes of romantic attraction, self-esteem, intelligence and the art of conversation with hilarious pratfalls, physical comedy and sight gags. Even iconic film critics Gene Siskel and Roger Ebert agreed on how wonderful this romantic comedy was, commenting on its effervescence and Martin’s ability to take the story of Cyrano de Bergerac and successfully make it his own. Plus, you can’t help but smile whenever Martin’s prosthetic nose shows up on screen. —Anita George


72. How Stella Got Her Groove Back (1998)

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Twenty years after Stella met Winston in Jamaica, and we’re still routinely bombarded with films where 40-year-old men are in relationships with 20-something women, and no one bats an eye. And, of course, the reverse is hardly ever depicted. Stella Payne’s story—that of a successful stockbroker in her 40s who finds a 20-year-old boy toy (turned genuine romantic interest)—would be a wonder to see on screen today. But it was never meant t ok be an especially complicated movie. The premise is simple, the setting is gorgeous and the cast is perfect. You can’t really beat Angela Bassett and Taye Diggs mingling and making love under the sun in Montego Bay. But it’s important to note that the movie also succeeds as a portrait of friendship (and also grief), with Whoopi Goldberg as Stella’s best friend, accomplice and life saver, Delilah. The movie was not without its flaws (including a very Hollywood ending) but, as Hollywood continues to pay itself on the back for all its strides in diversity (completely ignoring issues like colorism and ageism), ask yourself—when’s the last time you saw a dark-skinned woman over 35, falling in love with a dark-skinned man, whilst her dark-skinned girlfriend cheers her on? How Stella Got Her Groove Back is a marvel, and a reminder that, in so many ways, the ’90s were good to us. —Shannon M. Houston


71. Notting Hill (1999)
Director: Roger Michell

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Like most good romantic comedies, everything about Notting Hill is an absolute dream: Oh, you’re a world-famous American actress, wealthy and beloved by millions? Neat. And you’re staying in one of the most beautiful neighborhoods in London (one of the most beautiful cities in the world)? Super cool. But oh no! You collide with a guy in the street, and he spills orange juice all over you! Life is ruined! But wait a second. He’s an adorable independent bookstore owner with a group of quirky friends (including a hilarious Rhys Ifans and a pre-Downton Abbey Hugh Bonneville) and a penchant for spitting out screenwriter Richard Curtis’ (Four Weddings and a Funeral, Love Actually) charming one-liners and the face of Hugh Grant, and this is your meet-cute. Anna (Julia Roberts) may “just be a girl, standing in front of a boy, asking him to love her” … but she’s a damn lucky girl. —Bonnie Stiernberg


70. Lars and the Real Girl (2007)
Director: Craig Gillespie

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Lars and the Real Girl’s premise should have been cringe-worthy: Ryan Gosling dates a life-sized sex doll, and the entire town goes to great lengths to protect the fairy tale. But Nancy Oliver’s Oscar-nominated script is so gentle, and so melancholic, that it becomes a quietly powerful story of a stunted man who finally comes of age. Darkly funny but sweet-natured, Lars is a small treasure. —Jeremy Medina


69. About a Boy (2002)
Directors: Chris Weitz, Paul Weitz

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No stranger to romantic comedies, Hugh Grant delivered perhaps his best performance ever in About a Boy, a different kind of rom-com. Through his relationship with a young teenager, Grant subtly transforms from notorious womanizer into, well, a man capable of loving the beautiful Rachel Weisz. Grant’s relationship with the boy is tender and thoughtful, much like the film itself. —Jeremy Medina


68. Shakespeare in Love (1998)
Director: John Madden

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Shakespeare can be found throughout this list, as modern takes on his comedies abound, but Marc Norman and Tom Stoppard’s Oscar-winning original script puts the historical romance in romantic comedies, serving up a film that provides a rousing look at Elizabethan theater (and the characters who populated it) as it imagines the real inspiration for some of William Shakespeare’s early successes. Joseph Fiennes stars as the Bard and Gwyneth Paltrow as Viola de Lesseps in a film that is a treasure trove of references and mood for lovers of Shakespeare and of theater in general. (Its presentation of Romeo and Juliet is among the best film adaptations of the tragedy, even though it’s just in the background here.) But John Madden’s film is not just for Bardolators—the non-initiated will find the combination of Fiennes and Paltrow (and Geoffrey Rush, Colin Firth, Ben Affleck and Judi Dench) and this tale of star-crossed love both joyous and heart-wrenching. They might also decide this Shakespeare guy is worth checking out. —Michael Burgin


67. But I’m A Cheerleader (1999)
Director: Jamie Babbit

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In our current climate, it feels strange to have a gay conversion therapy camp serve as the backdrop for a love affair between two young women. Especially now that we know the devastating psychological effects that those practices can have on the people sent to be “changed.” But the core message of this late ’90s gem is clear: our LGBT+ brothers and sisters were born this way and they deserve love just as much as we do. Luckily for our heroine Megan (Natasha Lyonne), she finds that love with Graham (Clea DuVall), another kid sent by her parents to be converted to heterosexuality. Their connection and chemistry is immediate, given life by the understated and thoughtful performances by the two leads. —Robert Ham


66. Something Wild (1986)
Director: Jonathan Demme

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Something Wild offers the odd-couple pairing of Charles Driggs (Jeff Daniels), a vice-president of a banking company living a comfortable existence in a Long Island suburb, and Audrey Hankel (Melanie Griffith), a free-spirited woman seemingly without attachments, but also with a lot of money at her disposal to fund her devil-may-care ways. At first introducing herself to Charles as Lulu, Audrey basically ropes this yuppie into following her on a bizarre road trip throughout a good part of the East Coast—an adventure that, true to genre form, encompasses everything from screwball comedy to violent thriller, with the tone often shifting on a dime. Certainly, Demme’s film lives up to its title just in the all-over-the-place story it weaves. But the film is more than just the sum of its deliberately disparate parts—especially because neither of these two characters can be easily pinned down as types. The first time we see Charles in the film, he’s walking away from a diner having not paid for his meal—an act he later justifies as his way of rebelling within the system. Whether that is in fact true or not, it’s nevertheless clear that he does have certain unruly impulses in him just itching to pop out—which naturally catches the eye of someone like Audrey, who has made such unruliness her life’s mantra. But Audrey isn’t simply the kind of character who would later become known as the “Manic Pixie Dream Girl.” Both Audrey and especially Charles do learn new things about themselves during this odyssey—but it’s not as simple as Audrey learning the dangers of her unfettered lifestyle and Charles becoming more of a bad-ass by embracing that same lifestyle. Instead of being about self-improvement, Something Wild is more about self-awareness: a realization of how complex human beings can be. —Kenji Fujishima


65. As Good as It Gets (1997)
Director: James L. Brooks

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Jack Nicholson  is not exactly the first person who comes to mind when you think romantic leading man. Certainly, when we first meet Melvin Udall, the mean-tempered, OCD-afflicted curmudgeon at the center of James L. Brooks’ As Good As It Gets, it’s clear he’s no Tom Hanks. That is, until he is one day forced to take care of his neighbor’s dog. This event serves as the catalyst for a poignant Scrooge-like transformation: More in touch with his feelings, Melvin soon grows close to the single-mother/waitress (Helen Hunt) at his favorite restaurant and, in the end, overcomes his self-centeredness and lets her know how highly he thinks of her. Cheesy? Yes. But damn if it doesn’t work. —Mark Rozeman


64. Splash (1984)
Director:   Ron Howard  

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You know those moments when you unexpectedly discover you have crossed paths with a mermaid and suddenly you start wondering if that near-death experience you thought you had at Cape Cod when you were a kid miiiiiight have been something deeper and weirder? That! One of the first pictures to emanate from Disney’s spankin’ new Touchstone imprint (PG for mildly vulgar language?!) this mild-mannered, warm-hearted comedy, directed by Ron Howard, stars Tom Hanks as a lonely produce wholesaler and Darryl Hannah as the not-so-little Little Mermaid who saves him. From drowning. Literally, followed by figuratively. C’mon guys: metaphor! Aside from being credited with popularizing “Madison” as a name for girls, the film was a box office and critical success for its gosh-darned old-fashioned sweetness and for the great performances by Hanks and Hannah as well as classics from John Candy and Eugene Levy. Ron Howard is a natural at the Wistful School of Comedy and this film is a basically wall-to-wall feel-good. If you’re looking for a rom-com with sharp teeth, keep walkin’-but any fan of Tom Hanks as a rom-com lead needs to see this film. —Amy Glynn


63. Forgetting Sarah Marshall (2008)
Director: Nicholas Stoller

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Following one of the standard romantic comedy tropes, a man (in this case played by Jason Segel) is tempted to chase the wrong girl (Kristen Bell), ignoring the soulmate (Mila Kunis) right in front him. But while we’d seen the set-up before, we’d seen nothing like Segal’s character Peter getting dumped while naked, Russell Brand as the lead singer for Infant Sorrow or Peter’s A Taste For Love Dracula-themed puppet-comedy-rock-opera. Everyone you’d expect (Jonah Hill, Paul Rudd, Kristen Wiig, Bill Hader) co-stars. —Josh Jackson


62. Pretty in Pink (1986)
Director: John Hughes

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Let’s ignore the fact that she ends up with the wrong guy in the end (Team Duckie for life!) and examine what makes Pretty in Pink’s Andie so impossibly cool: She works in a record store and has killer taste in music. Her outfits are daring and incredible. She brushes off insults from evil richie-rich Steff (James Spader) like they ain’t no thang. She supports her deadbeat dad and essentially serves as head of their household. But most importantly, she’s the picture of courage, staying true to herself the whole way through and never changing to please Blane and his wealthy friends—and if there’s any single movie character teen girls should be modeling themselves after as they attempt to swim the treacherous waters of high school (and high school romance) without drowning, she’s the one. —Bonnie Stiernberg


61. Beauty and the Beast
Directors: Gary Trousdale and Kirk Wise

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The first animated film to be nominated for a Best Picture Oscar, Beauty and the Beast, along with The Little Mermaid in 1989 and The Lion King in 1994, composed the last push of classic hand-drawn cartoons before Toy Story tipped the form definitively toward computer animation. As with so many Disney princesses, the role of Beauty (voiced by Paige O’Hara) is to find her prince, but she’s got a little feminist kick to her, constantly burying her nose in a book, dreaming of escaping her provincial life and rejecting the advances of the handsome oaf Gaston (Richard White). When her father, an idiosyncratic inventor whose character design smacks of Albert Einstein, gets lost in the woods and stumbles upon an enchanted castle, its inhabitant—a horrible Beast (Robby Benson)—takes him prisoner. Belle discovers her father’s captivity and offers to take his place. Her arrival is fortuitous, as time is running out to reverse the curse that has rendered Beast so, well, beastly and his staff a raft of household items, including a candelabra named Lumiere (Jerry Orbach), a mantel clock named Cogsworth (David Ogden Stiers), and a teapot named Mrs. Potts (Angela Lansbury). These charmed servants conspire to tame the Beast so that he’ll fall in love with Belle, and she with him, thus breaking the spell that has trapped them in bric-a-brac. The film’s major set pieces are thrilling, especially the Broadway-infused “Be Our Guest” number by Howard Ashman, whose jaunty lyrics seem as familiar today as they did in 1991, and Alan Menken, whose score won an Academy Award. If you like your rom-coms animated and musically inclined, the House of Mouse provides. —Annlee Ellingson


60. Grosse Pointe Blank (1997)
Director: George Armitage

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In the role that probably set the foundation for High Fidelity’s Rob, rom-com mainstay John Cusack plays Martin Q. Blank as a vaguely charismatic, vaguely confident, vaguely organic hitman—the kind of guy one would never suspect is good at killing people for a living. Except: Blank is from the vaguely wealthy Detroit suburb of Grosse Pointe, which means that he’s one of many formless Michigander large adult sons who go on to do things no one has ever expected of them. Before the 2008 Recession, Oakland County, one of Detroit’s surrounding counties, a very popular member of the Metro Detroit family, was among the absolute richest counties in the country. Like Orange County rich. And still no one seems to really remember that—back in even 1997, when the car companies were slaying, no one expected much from a Michigander. Grosse Pointe Blank epitomizes that befuddling state-wide middle child complex in John Cusack’s thoroughly, anxiously casual performance, mapping that angst of arrested development over a wacky love story with old girlfriend Debi (Minnie Driver). —Dom Sinacola


59. Moonstruck (1987)

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“Snap out of it!” A rom-com with a genuinely romantic sensibility (the hopeless kind), Moonstruck is a basically undeniably adorable comedy about chance, family and what it means to “settle.” Pragmatic widow Loretta (Cher) agrees to marry a nice sensible guy (Danny Aiello), but soon finds herself in a sitch with his passionate and mercurial younger brother Ronny (Nicolas Cage). Cher’s comedic chops are not insignificant, and the chemistry between her and Cage is great. The film has an incredible wealth of wonderful supporting performers (perhaps most notably Olympia Dukakis, who plays Cher’s mother). Norman Jewison’s directorial sensibility here might not qualify as “high art” but it’s a damn fine rom-com, with crackling dialogue, tons of energy and seductively likable characters: Apaean to the joys and inevitable sorrows of dealing with your family, this film has spirit and smarts and soul. And a certain image of Cher in opera garb kicking a beer can up a silent Brooklyn street that one could be forgiven for characterizing as “iconic.” —Amy Glynn


58. Bridesmaids (2011)
Director:   Paul Feig  

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Unlike The Hangover, which was basically a long comedy sketch, Bridesmaids is actually a movie. This is always the big question when it comes to comedies. Should you aspire to make a full cinematic experience and risk coming up short (Wedding Crashers) or do you simply shoot for nonstop emotionless laughs and achieve wild success at a less transcendent achievement (Anchorman). Bridesmaids is thoroughly hilarious, complete-narrative cinema thanks to the brilliance of Kristen Wiig. And it has staying power in the typically bro-dominated pantheon of film comedy. —Ryan Carey


57. Breakfast at Tiffany’s (1961)
Director: Blake Edwards

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It can be difficult to overlook the extreme racism of Mickey Rooney playing a Japanese landlord in Blake Edwards’s beloved classic. Nobody should have any problem with people who refuse to watch a movie with such a character in 2018. If you can look past his brief scenes, though, you’ll find a romantic comedy that deserves its iconic reputation. It features Audrey Hepburn at her finest, and is the main reason every Anthropologie is full of books and art prints about her. It’s a romantic comedy that’s both romantic and funny (and, yes, rather racist). —Garrett Martin


56. My Big Fat Greek Wedding (2002)
Director: Joel Zwick

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The little indie rom-com that could, Joel Zwick’s My Big Fat Greek Wedding was the surprise hit of 2002 thanks to a hilarious, loving portrayal of Greek-American culture that hadn’t been seen much on the big screen. Nia Vardalos plays Toula Portokalos, who to the consternation of her family, is engaged to a decidedly non-Greek man. The clash of cultures is at the center of this funny and original film based on Vardalos’ Oscar-nominated screenplay. —Josh Jackson


55. You’ve Got Mail (1998)
Director: Nora Ephron

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Some films are just pure testaments to the power of relatable characters and believable screen chemistry, and Nora Ephron’s You’ve Got Mail is a prime example. Dramatically unsurprising and artistically unremarkable, it still pulls you in with its Jane Austen-esque lover-rival dynamic and general good-naturedness. The third rom-com collaboration between Tom Hanks and Meg Ryan (and Ryan’s most unaffected performance of the trio) is the story of the unlikely (yet inevitable) coupling between an independent bookstore owner and the mogul at the helm of the mega-bookstore that’s threatening to put her out of business. In real life they can’t stand each other—but in an anonymous chat room, they get along and then some. Sailing along on the sheer likability of its protagonists, and the actors who portray them—Ryan’s at her best in a grounded, just-plain-happy performance and Hanks’s kind of limitless plasticity is in full flow—You’ve Got Mail trades in “cute.” If that makes you itch, you’re in for a bit of scratching, but there is a genuine heart to this movie that will reel in even avowed cynics. —Amy Glynn


54. Appropriate Behavior (2014)
Director: Desiree Akhavan

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By default, being a twenty-something is messy—whether it’s dealing with crumbling relationships, jobs you’re too inexperienced for or the lies you tell to appease your parents. Desiree Akhavan explores that universal experience of untangling our identities in 2014’s Appropriate Behavior. Shirin (Akhavan) is a secretly bisexual woman fresh out of a break-up and dedicated to getting ?over her ex-girlfriend. But Shirin’s dispirited attempts to push every aspect of her life back on track fall awkwardly and disappointingly flat at every turn. Shirin can talk her way into a job and a date, but can she keep either? Appropriate Behavior follow one woman’s journey through life telling everyone she’s an adult … until she accidentally becomes one. Rather deftly, Akhavan’s film serves as a commentary on translation—the differences between the language we use, the things we actually mean, and how it all gets twisted. The narrative plays with Shirin’s identities—as an Iranian, a woman, a millennial and a bisexual—sometimes hilariously, other times rather poignantly. All 86 minutes of the film are spent watching Akhavan’s character desperately and unsuccessfully try to say what she wants. But as the responsibilities, one-night stands and brushes with her ex mount, Shirin begins to realize that the real trick to communication is taking the time to understand yourself before trying to communicate that to someone else. Appropriate Behavior is undoubtedly a comedy, but also a heartfelt look at how we learn to say what we mean and be who we are. —Abbey White


53. 13 Going on 30 (2004)
Director: Gary Winick

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What could’ve been easily dismissed as a shameless Big ripoff might be even better than that Tom Hanks classic. Jennifer Garner is at her most charming as a 13-year-old in a grown-up’s body, and perennially underrated Judy Greer shines in her finest film role as Garner’s best frenemy. The gently nostalgic script might deserve the most credit, though—a movie like this could have been ruined by lethal levels of cheese, but 13 Going on 30 has the exact right amount of crowd-pleasing schmaltz. —Allyn Moore


52. The Wedding Banquet (1993)
Director:   Ang Lee  

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The Wedding Banquet, Ang Lee’s foray into a kind of screwball comic style, is his first time examining the lives of gay people. Wai-Tung Gao (Winston Chao) is constantly badgered by his parents to get married, now that he’s in his late 20s, but as dramatic irony would have it, he’s a successful Manhattanite living with his boyfriend, Simon (Mitchell Lichtenstein, son of artist Roy), the two straining to use their quick wits to come up with excuses to stave off Wai-Tung’s marriage. At the behest of Simon, as if to get Wai-Tung’s old-fashioned parents to stop bothering them, he suggests Wai-Tung marry one of his apartment tenants, in turn scoring her, Wei Wei (May Chin), a green card. The couple invite Wai-Tung’s parents to the United States, plan a large wedding and chaos ensues.

In The Wedding Banquet, homosexuality or queerness is enough to transgress tradition. Which sounds obvious but is significant not only because of Wai-Tung’s implied upper middle-class status, but because of the complicated racial dynamics that, too, exist in the film. Wai-Tung’s partnership with a white man is, not unlike the interracial marriage in Ang Lee’s first film, Pushing Hands, easily read as either a move forward into a modern world of modern relationships, or a threat to some idea of racial purity within Asianness (an idea in Crazy Rich Asians). The Taiwanese diaspora at work, folks. —Mark Rozeman


51. Houseboat (1958)
Director: Melville Shavelson

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In a lot of ways, Houseboat is a bit of a trivium, although it’s never unsatisfying to watch Cary Grant or Sophia Loren, like, ever. Grant plays a widowed father who takes his rather bratty and coddled children to live on a busted-up houseboat, ends up with Sophia Loren as his housekeeper and falls in love with her. A big star vehicle with a kind heart, Houseboat won’t strike everyone as cinematic dynamite, especially when there is really one standout feature to this film (significant because it was really unusual for its time). This film is very focused on the emotional world of the children, surprisingly clear-eyed and perspicacious about the mixed feelings kids have when their parents re-partner. Falling in love with Sophia Loren is easy. Winning back the hearts of your disaffected children? That’s tougher—but worth watching if for no other reason than to see Grant take it on with his typical panache. —Amy Glynn


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