The 100 Best Comedies of All Time

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75. 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 non-stop 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


74. Four Weddings and a Funeral (1994)
Director: Mike Newell

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The first of several Richard Curtis-penned rom-coms starring Hugh Grant, Four Weddings and a Funeral follows our favorite bumbling Englishman as he repeatedly runs into the love of his life at—you guessed it—four weddings and a funeral. While much of the movie is lighthearted and some of it borders on cheesy (see Andie MacDowell’s infamous “Is it still raining? I hadn’t noticed” line in its finale), its graver moments, like Fiona (Kristen Scott Thomas) dealing with unrequited love or the titular funeral, remind us that love may be goofy and complicated and wonderful, but finding that one true love is serious business. The Academy agreed, nominating the film for Best Picture in a stacked year that included Forrest Gump, Pulp Fiction and The Shawshank Redemption. —Bonnie Stiernberg


73. Harvey (1950)

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Wealthy, affable drunk plus imaginary 6’4” bunny equals Pulitzer Prize, Broadway smash, and film adaptation starring the inimitable Jimmy Stewart as Elwood P. Dowd, whose drunken antics are not a problem for the locals until he starts claiming to see a pooka (a trickster spirit from Irish folklore). Suddenly, Elwood’s not so acceptable any more. Except Harvey, the imaginary rabbit, exerts an odd transformative effect on the other characters—with the exception of Elwood’s snobby sister Veta (Josephine Hull), who by the way is the only other person who can see Harvey. Veta tries to have Elwood committed to a mental hospital (his rabbit-antics are interfering with her plans to marry her daughter Myrtle (Victoria Horne) to A Good Match). Veta ends up getting herself committed instead, but the hospital director, Dr. Chumley, begins seeing Harvey as well (awkward…). A whimsical little fantasy/farce with a warm heart, Harvey is also a bit of a meditation of tolerance and the merits of “reality”; the drunken and possibly addled Elwood is significantly happier than the “normals” who surround him. It’s a lightweight film, but the sheer force of James Stewart’s charisma could make just about anything riveting. Even an invisible bunny. —Amy Glynn


72. Clueless (1995)
Director: Amy Heckerling

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The Beverly Hills reboot of Jane Austen’s classic Emma was a sleeper smash in 1995 and, much more importantly, gave the phrase “As if!” to pop culture. Alicia Silverstone is Cher, a pretty, vain, superficial LA teen who goes on a mission to turn ugly-duckling classmate Tai (Brittany Murphy) into a Superswan, only to find herself eclipsed and adrift. A soft-edged satire of nouveau-riche Angeleno culture and simultaneously of the teen rom-com genre, Clueless is neither the most subtle nor the most hard-hitting film of its era, but it’s surprisingly seductive, in large part thanks to Amy Heckerling’s scrupulously researched script, which captured a dialogue style that both represented and influenced teen-speak of the time. —Amy Glynn


71. Sherlock, Jr. (1924)
Director: Buster Keaton

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You could make a highlight reel of classic silent comedy moments using only Buster Keaton’s Sherlock, Jr., and no one could justly complain. In the 91 years since Keaton made his love letter to cinema, no one has crafted a better examination of the relationship between the audience and the silver screen. Keaton plays a movie theater projectionist and wannabe detective who dreams he walks into a movie screen and becomes a suave hero—the perfect metaphor for the appeal of the movies. He plays with reality through virtuoso special effects, but also captures genuine stunts in single takes. (He broke his neck in one scene and still finished the take.) He daringly subverts structure—the conflict is resolved halfway through the movie with no help from the hero. He brings visual poetry to slapstick with rhyming gags. The laughs coming from failure in the real world and serendipity in the fantasy movie world, but the mechanics parallel each other. And he strings it all into a romp that never stops moving toward more hilarity. —Jeremy Mathews


70. Midnight Run (1988)
Director: Martin Brest

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The ’80s created the textbook action/comedy formula, and director Martin Brest was smack dab in the middle of it. His Beverly Hills Cop was originally written as a straight action movie, until Eddie Murphy was cast in the lead role. Instead of keeping the overall self-serious tone of the film and just inserting some out-of-place comedy set pieces into the narrative, Murphy and Brest infused a lighthearted tone across the entire project, while keeping the basic requirements of an action structure in place. Midnight Run, Brest’s follow-up to Beverly Hills Cop, perfects this fusion. None of the action sequences take themselves too seriously, and none of comedy comes across as mugging, desperate to extract easy chuckles. The premise and structure are very simple and fairly predictable: It’s a traditional road movie wherein a grizzled bounty hunter (Robert DeNiro) has to transport a mob accountant (Charles Grodin) across the country, with the mob and the police squarely on their tail. What makes Midnight Run still feel fresh after 30 years is Brest’s aforementioned handle on tone, and the terrific chemistry between DeNiro and Grodin, so on point it’s surprising they weren’t reunited for other similar flicks after this. Usually the rough masculine bounty hunter would be the wild card against the accountant’s stuffy straight man, yet DeNiro and Grodin find refreshing ways of tinkering with that formula, with DeNiro’s character eventually coming across as a regular good guy who was dealt more than a few bad hands, and Grodin as a lovable but sometimes infuriating weirdo. —Oktay Ege Kozak


69. South Park: Bigger, Longer & Uncut (1999)
Director: Trey Parker

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South Park creators Trey Parker and Matt Stone’s philosophical reasoning behind the big screen adaptation of their massively popular TV show can be summed up in a quick exchange in the film: After the South Park kids suddenly “contract” potty mouth via Terence and Philip’s R-rated movie, a delicious bit of meta commentary, Mr. Garrison is pissed when the kids can’t seem to stop spewing the f-word. To which, Kyle replies, “What’s the big deal. They’re just words. Fuck, fuckity, fuck, fuck, fuck!” U.S. culture has always been up its own ass about crude language, yet is willing to not only turn a blind eye to horrific and senseless violence. Parker and Stone solidify this point when the country so easily plunges into fascism because of some trivial shit (sound familiar these days?), that they ignore the countless deaths around them as they literally do Satan’s (and Saddam Hussein’s) bidding. Yes, this coarse and crude cartoon about 4th grade kids making fart jokes created one of the most potent satires on American culture as we headed into the new millennium. Nowadays Parker and Stone are known for such subversion, but at the time when the show was only in th emidst of its third season, Bigger, Longer & Uncut was downright revolutionary. And it still holds up thanks to the seemingly unending barrage of American hypocrisy we experience daily. —Oktay Ege Kozak


68. The Birdcage (1996)
Director: Mike Nichols

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You know what’s awkward? When you’re a middle-aged gay Jewish South Beach drag club owner (Armand, played by Robin Williams) and your straight son shows up and asks for your blessing to marry his girlfriend who is the daughter of a Neocon senator (Gene Hackman) who heads something called “The Coalition for Moral Order.” You want to support your kid, but you don’t love being closeted by him, and the dinner meet-up ends up meaning you and your partner, Albert (Nathan Lane), are forced into a whole new level of drag in which you are straight, a cultural attaché to Greece, and married to the one-night stand straight-sexperiment (Katherine, played by Christine Baranski) that led to the conception of your son. Your partner’s offended, the Senator’s being investigated by the tabloids, tensions are running high and your houseboy Agador (Hank Azaria) has agreed to transform into a Greek butler named “Spartacus,” but let’s face it, tensions are running high on all sides-and that’s before your baby-mama gets caught in traffic and Albert sees the opportunity for the drag role of a lifetime. Fully Shakespearean hijinks ensue. The 1996 Mike Nichols remake of Edouard Molinaro’s La Cage Aux Folles was not really blistering social commentary, but beneath its glib feel-good star-vehicle exterior there are some depths you could easily miss while you’re distracted by the batshit-crazy and heavily sequined antics of Williams and Lane. It’s actually not only rambunctious and witty but, as with many of Robin Williams’ film roles, The Birdcage has a serious streak where a genuine investigation of personal identity is underway, and hypocrisy, acceptance, snobbery, and most of all, everyone’s individual style of “drag” (and hey, we all have one, even if we don’t always express it by putting on fake lashes and singing Sondheim) gets taken out for a much-needed exam. —Amy Glynn


67. Punch-Drunk Love (2002)
Director:   Paul Thomas Anderson  

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It may be hard to recall, but there was once a time when the world believed in Adam Sandler—and we have P.T. Anderson to thank for such a glimpse of hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize with Inherent Vice. But far from a bit of fluff or a reactionary stab at a larger audience, Punch-Drunk Love is what happens when a director with so much untapped potential just sort of throws shit at the wall to see what sticks. A simple love story between a squirmy milquetoast (Sandler) and the woman (Emily Watson) who yanks him from his stark blue shell, the film is part musical, part silent film and all surreal comedy. That this is Sandler’s best role is hardly up for debate; that this may be Jon Brion’s best soundtrack is something we can talk about later. That the rest of the film, which in any other director’s hands would be a total mess, feels so exquisitely felt is almost … magical. And that? That’s that, Mattress Man. —Dom Sinacola


66. The Apartment (1960)
Director: Billy Wilder

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Filmmaker Billy Wilder had perhaps one of the greatest, most diverse track records in film history from 1944 to 1960. In this period, he tackled an Oscar-winning drama about alcoholism (The Lost Weekend), two well-regarded film noirs (Double Indemnity, Sunset Boulevard), a war drama (Stalag 17), two light-hearted rom-coms (Sabrina, Seven Year Itch) a gripping murder-mystery (Witness for the Prosecution) and perhaps the funniest American movie of all time (Some Like It Hot). Yet, of all these golden credits, one Wilder’s most beloved and memorable achievements was 1960’s The Apartment. Jack Lemmon plays C.C. Baxter, an ambitious office worker who, desperate to climb the corporate ladder, allows his bosses to use his apartment to carry on discreet affairs with their mistresses. Things get complicated, however, when he discovers that his office crush, quirky elevator operator Fran Kubelik (Shirley MacLaine), is one of his bosses’ mistresses. While it actually gets quite dark at times, The Apartment strikes a perfect balance between laugh-out-loud comedy and emotionally honest drama. Following the career highlight that was his drag-heavy performance in Some Like It Hot, Lemmon here proves that he can play the low-key, straight man with equal dexterity. Likewise, MacLaine’s charming portrayal as the damaged, yet lovable Kubelik would provide the model for manic pixie dream girls for years to come. —Mark Rozeman


65. Trading Places (1983)
Director: John Landis

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A biting take on the The Prince and the Pauper story as filtered through the prism of the Decade of Greed, Trading Places stars Dan Aykroyd and Eddie Murphy as, respectively, high class broker Louis Winthorpe III and homeless street vagrant Billy Ray Valentine. As part of a “nurture vs. nature” experiment by the Duke Brothers, two wealthy, yet unscrupulous business magnates, Louis and Billy end up abruptly, per the title, trading places on the social ladder. The Dukes frame Louis for drug dealing, resulting in him losing both his job and his girlfriend, and then bail Billy out of jail and provide him with Louis’ old job and high-class apartment. Once Billy and Louis discover this deception, they launch a plan for vengeance. Featuring both Murphy and Aykroyd at the top of their game, Trading Places represents a prime example of the kind of smart, yet decidedly un-PC comedies that could only exist at a certain point in the ’80s (Aykroyd’s blackface-heavy disguise in one scene, for example, would never fly in today’s market). A stone-cold ’80s classic if there ever was one. —Mark Rozeman


64. Waiting for Guffman
Director:   Christopher Guest  

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The first of Christopher Guest’s three mockumentaries co-written with Eugene Levy, Waiting for Guffman introduced the world to a cast that would form the backbone of their other projects. The film picked up on This is Spinal Tap’s tradition while bringing a decidedly sweeter tone to the table. Corky St. Clair leads the lovable bunch of misfits who comprise the small-town theater group. They are determined to catch the eye of Broadway producer Mort Guffman, as they put on a play about their town’s history, Red, White and Blaine. Needless to say, things go wrong in all the right ways. —Amanda Wicks


63. Dumb and Dumber (1994)
Directors: Peter Farrelly, Bobby Farrelly

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There is a special brand of nihilism at play in the Farrelly Brothers’ debut, one which vaunts stupidity above all else, not because the Farrellys want to celebrate being dumb over being smart, but because they seem to find no real consequences in the kind of ignorance inhabited by Lloyd (Jim Carrey, beloved) and Harry (Jeff Daniels, best role of his career) to the extent that morality for these characters is moot. Devoid of the brain power required to fully comprehend the vast world around them, operating on little more than teenage horniness and threats of unemployment (plus the image of a decapitated parakeet), Harry and Lloyd blissfully become involved in a kidnapping caper concerning the husband of wealthy heiress Mary Swanson (Lauren Holly). It works out as one might expect—in that it doesn’t work out, and that doesn’t matter—but not without developing a lot to love in these two dipshits, making its sequel feel unrelentingly mean-spirited by comparison. It shouldn’t be surprising then that pretty much every other Farrelly movie (sans There’s Something About Mary) has aged poorly: America doesn’t need any more movies that seem to actually honor our dumbest assholes. —Dom Sinacola


62. The 40-Year-Old Virgin (2005)
Director:   Judd Apatow  

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Judd Apatow  has emerged as the major new voice in the world of romantic comedy. His first directorial effort, The 40-Year-Old Virgin is a big, goofy, hilarious mess of a movie that is anchored by the easy charm of its two principal leads, Steve Carell and Catherine Keener. Their no-nonsense romance is surprisingly understated and adult in a movie with an outrageous premise and lewd jokes. Leslie Mann also deserves credit for that hilarious French toast scene. —Jeremy Medina


61. City Lights (1931)
Director: Charles Chaplin

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In his later years, Charlie Chaplin was known for bringing pathos into his comedy whenever he had the opportunity. City Lights is the movie where he earns every bit of it. While its structure resembles Chaplin’s usual picaresque format, there’s more of a deliberate purpose as the tramp tries to help a poor, blind flower girl, played adorably by Virginia Cherrill. Harry Myers also deserves a mention for his performance as the millionaire who’s generous when he’s drunk and can’t remember his good deeds when he’s sober. —Jeremy Mathews


60. Harold and Maude (1971)
Director: Hal Ashby

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The original Daily Variety review begins “‘Harold and Maude’ has all the fun and gaiety of a burning orphanage.” History has been kinder. Though it may be the darkest film on this list, Harold and Maude is certainly a romantic comedy. Young Harold (Bud Cort) and 79-year-old Maude (Ruth Gordon) do find love. And it is wickedly funny as Harold finds increasingly more gruesome ways to scare off the suitors sent by his mother. But Hal Ashby’s masterpiece is unlike anything we’ve seen before or since its 1971 release, and Gordon is brilliant as the manic pixie dream septuagenarian. Just don’t go in expecting a happily ever after. —Josh Jackson


59. Lost in America (1985)
Director: Albert Brooks

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Lost in America is the perfect 1980s counterpoint to Easy Rider. As America became more materialistic and self-centered during the ’70s and ’80s, as yuppies replaced the hippies, material happiness became more attainable for average (mostly white) middle-class Americans, millions trying in vain to fill the spiritual hole inside them with cars, homes and any spiffy stuff that distracted from the boredom. David Howard (Albert Brooks), the financially secure but emotionally unfulfilled ad man at the center of Brooks’ quintessential ’80s comedy, finds himself in the middle of such inner conflict. He just got passed over for a well-deserved promotion at a job he hates anyway, so he decides to enact his favorite movie, Easy Rider, and goes on a trip to “find America” with his equally supportive and apprehensive wife Linda (Julie Hagerty in the best performance of her career). As soon as the couple’s spiritual quest begins, their ’60s idealism immediately clashes with their ’80s materialism. Are they too domesticated by ’80s culture to truly free their minds? —Oktay Ege Kozak


58. Dirty Rotten Scoundrels (1988)
Director: Frank Oz

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The story of two rival con men working a wealthy heiress is a comedy classic for two reasons: Steve Martin and Michael Caine. Watching Martin’s American street hustler Freddy Benson try to learn from and outwit his reluctant mentor, Caine’s refined British Lawrence Jameson, while they both desperately attempt to win a bet of swindling $50,000 from their agreed mark (Glenne Headly as Janet Colgate), offers plenty of laughs, even if the plot is fairly conventional. With Benson reduced to playing the dimwit Ruprecht, Steve Martin is in his physical comedy prime. —Josh Jackson


57. The Producers (1967)
Director: Mel Brooks

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In the ’50s and ’60s Mel Brooks was just a comedian, albeit a particularly brilliant one. He wrote for TV shows like Your Show of Shows and Get Smart, and had a hit comedy duo with Carl Reiner that spawned three records in two years. But in writing and directing The Producers—the now-iconic story of a Broadway producer known for his flops (Zero Mostel) and a meek accountant (Gene Wilder) who team up to rob investors by deliberately sinking a musical about Adolph Hitler—Mel Brooks may have become the prototypical comedian-director as we currently understand the phrase (for talkies, at least.). The Producers is just as funny as ever, though amusingly tame in comparison to the uproar it caused and the producers who refused to touch it. It’s also completely different from the meta-gag-fests of Young Frankenstein and Blazing Saddles. But it announced Brooks as the champion of weird comedy on film for the rest of the 20th century, and, due to its release as an art-house film, made him a new kind of auteur. —Graham Techler


56. Mean Girls (2014)

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Aside from the greatness of its one-liners, Mean Girls has endured because it’s a cinematically exaggerated version of the truth. Teen life really does feel like being on safari, with the same mad hormones, territorial urges and competitive edge. And girls really can have a hive mentality, clinging to whatever imperceptible alliances will allow them to curry favor with the most popular among them. In the shape of Regina George, Mean Girls shows how the prettiest girls are often raised to the position of Alpha—and boy, can it go to their heads. —Christina Newland


55. Broadcast News (1987)
Director: James L. Brooks

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One of the sharpest written, best-acted romantic comedies of the ’80s, Broadcast News soars on the performances of Holly Hunter, William Hurt and Albert Brooks. Sure, it says things about the state of media—some of which are pretty prescient—but watching the film’s three leads inhabit their characters is a joy in and of itself. —Michael Burgin


54. The Gold Rush (1925)
Director: Charles Chaplin

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The Klondike gold rush made the perfect setting for Charles Chaplin’s tramp to run wild. Chaplin took all the motifs he could find from adventure novels, melodramas and other stories of the northern frontier, tossed them in a blender and served up a collection of what would become his most famous scenes. He finds humor in peril—with a suspenseful teetering cabin scene, as well as starvation (when he famously makes a meal of his boot) and of course finds time to show off with his dancing roll scene. However, no one has succeeded in finding any humor in the atrocious voiceover Chaplin added to the 1942 rerelease. Be sure to watch the original version. For a more serious take on the Klondike hardships, see Clarence Brown’s The Trail of ’98 (1928).


53. The Royal Tenenbaums (2001)
Director:   Wes Anderson  

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Wes Anderson’s first two films took place in the Texas of his youth. The Royal Tenenbaums moves his storytelling to his adopted city of New York. And the story is one that bridges childhood and adulthood and the tremendous effects one has upon the other. The “Royal” in the title refers to Gene Hackman’s character. Royal Tenenbaum is the patriarch of a family of childhood prodigies: Chas (Ben Stiller), a math genius with a head for business; Richie (Luke Wilson), a tennis star; and adoptive daughter Margot (Gwyneth Paltrow), a playwright. The movie begins with Royal announcing his separation from his wife, Etheline (Anjelica Huston) before picking up years later with the children having gone on to great success and failure. As Etheline prepares to re-marry to her longtime accountant (Danny Glover), Royal announces that he has stomach cancer and attempts to reconcile with the family he abandoned. The family disfunction and struggle for redemption would become hallmarks of Anderson’s oeuvre, but here, with a talented cast that also included frequent collaborators Bill Murray, Owen Wilson and Kumar Pallana, the auteur’s gift for wringing humor out of hopelessness is unmatched. As every piece of set dressing, every item of clothing seems and every symmetrical camera frame seems painstakingly managed, the characters are spiraling out of control; their despair is deeply felt, and their redemption serves as a euphoric release. It’s a beautiful movie both visually and emotionally and remains Anderson’s crowning achievement after all these years. —Josh Jackson


52. Tootsie (1982)
Director: Sydney Pollack

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Can you imagine how audiences and critics might react to Tootsie if it came out in theaters today? Sydney Pollack’s film plays with gender roles and layers its portrait of an actor going full-drag with gay panic for giggles. You can just picture this film getting lambasted in 2015 for making a joke out of homophobia and for having the gall to ask viewers to sympathize with the plight of an actor who has to dress as a woman to find work. But the reason Pollack’s 1982 classic endures is because of its compassionate heart. This is a kind, empathetic movie that puts its hero, Dustin Hoffman’s cranky perfectionist thespian Michael Dorsey, in the shoes of his female peers to teach him (and us) a lesson, not to make snide jokes at the expense of the opposite sex. The humor is never mean-spirited; the message is rarely pompous, though when it is, that’s meant to be part of the point. Tootsie’s sharp comedy makes it a great piece of entertainment, but it’s the film’s sincere sensitivity that makes it timeless. —Andy Crump


51. A Christmas Story (1983)
Director: Bob Clark

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To wring something as genuinely warm and heartfelt as it is hilarious from a central theme of rampant consumerism is a rare thing. To supplant Christmas Day TV scheduling previously reserved only for classics like It’s a Wonderful Life and Miracle on 34th Street is quite another. Director Bob Clark assembles a pool of onscreen talent who were clearly born to inhabit Jean Shepherd’s treasured story of childhood amidst Major Awards, first swear words, cynical Mall Santas, and—of course—the ruminations on what it truly means to shoot your eye out. —Scott Wold

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