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Director Billy Wilder originally wanted Frank Sinatra as Jerry/Daphne.
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Marilyn Monroe required 47 takes to get "It's me, Sugar" correct, instead saying either "Sugar, it's me" or "It's Sugar, me". After take 30, Billy Wilder had the line written on a blackboard. Another scene required Monroe to rummage through some drawers and say "Where's the bourbon?" After 40 takes of her saying "Where's the whiskey?", 'Where's the bottle?", or "Where's the bonbon?", Wilder pasted the correct line in one of the drawers. After Monroe became confused about which drawer contained the line, Wilder had it pasted in every drawer. Fifty-nine takes were required for this scene and when she finally does say it, she has her back to the camera, leading some to wonder if Wilder finally gave up and had it dubbed.
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A preview audience laughed so hard in the scene where Jack Lemmon announces his engagement that a lot of the dialogue was missed. It had to be re-shot with pauses (and the maraca gimmick) added.
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Billy Wilder referring to Marilyn Monroe while making the movie: "We were in mid-flight, and there was a nut on the plane." Indeed, Wilder publicly blasted Monroe for her behavior, and she was not invited to the wrap party.
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The resort scenes were filmed entirely at the Hotel Del Coronado in San Diego, California. One reason why Billy Wilder chose this location was Marilyn Monroe's ongoing personal problems. He wanted a location where she could live on site and not have to be transported.
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Tony Curtis has said that he asked Billy Wilder if he could imitate Cary Grant for his stint as the millionaire in the movie. Wilder liked it and they shot it that way. Apparently, Grant saw the parody of himself and stated, "I don't talk like that."
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Danny Kaye and Bob Hope were considered for the roles that went to Jack Lemmon and Tony Curtis.
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In 2007, the American Film Institute ranked this as the #22 Greatest Movie of All Time.
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Voted #1 on the American Film Institute's list of 100 Funniest Movies.
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Voted #14 on the AFI's List of 100 Greatest Movies.
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In the opening scene when Joe and Jerry are playing at the "funeral", all of Gerald's "supposes" eventually become true: The Dodgers move from Brooklyn to Los Angeles and Mary Pickford and Douglas Fairbanks get divorced. Also, of course, the stock market crashed later in 1929.
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Marilyn Monroe was pregnant during the filming, as a result she looked considerably heavier. She had no known children and several miscarriages in her life. Due to her pregnancy, most of the publicity still photos were posed for by both Sandra Warner (who had an uncredited role as one of the band members) and Monroe's frequent stand-in Evelyn Moriarty with Monroe's head superimposed later.
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The railroad passenger car that was used in this movie (Clover Colony) is now at the Tennessee Valley Railroad Museum in Chattanooga, Tennessee where it can be used in excursion/local service.
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Tony Curtis's voice as Josephine was dubbed by Paul Frees (according to co-writer I.A.L. Diamond). Curtis confirmed it by stating the voice you hear as Josephine is a combination of his voice and Frees'. Curtis says he had trouble maintaining a high-pitched voice for an entire take.
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Stories of the difficulty that cast and crew had with Marilyn Monroe during the making of this film have grown to almost mythical proportions. In the "farewell" telephone conversation between Monroe and Tony Curtis, her side-to-side eye movements clearly reveal that she was reading her lines directly from an off-screen blackboard. According to Curtis, Monroe was routinely 2 to 3 hours late to the set, and occasionally refused to leave her dressing room.
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The film's working title was "Not Tonight Josephine".
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In Russia, the film is titled "Only Girls Are Allowed In Jazz"; thought by some to be a much more appropriate title.
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Was voted the 9th Greatest film of all time by Entertainment Weekly, and is ranked on this list high enough to be the greatest comedy of all time.
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Supposedly when Orry-Kelly was measuring all three stars for dresses, he half-jokingly told Marilyn Monroe, "Tony Curtis has a nicer butt than you," at which point Monroe pulled open her blouse and said, "Yeah, but he doesn't have tits like these!"
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Upon its original release, Kansas banned the film from being shown in the state, explaining that cross-dressing was "too disturbing for Kansans".
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According to Jack Lemmon, George Raft spent hours teaching him and Joe E. Brown how to tango.
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Premiere voted this movie as one of "The 50 Greatest Comedies Of All Time" in 2006.
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The film was adapted into a Broadway musical entitled "Sugar", which opened at the Majestic Theater on April 9, 1972 and ran for 505 performances.
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Marilyn Monroe wanted the film to be shot in color (her contract stipulated that all her films were to be in color), but Billy Wilder convinced her to let it be shot in black and white when costume tests revealed that the makeup that Tony Curtis and Jack Lemmon wore gave their faces a green tinge.
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A cabaret dancer (a man who played women on stage) tried to teach Tony Curtis and Jack Lemmon to walk in heels. After about a week, Lemmon declined his help, saying he didn't want to walk like a woman, but a man trying to walk like a woman.
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Anthony Perkins auditioned for the Jack Lemmon role.
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When Tony Curtis and Jack Lemmon first put on the female make-up and costumes, they walked around the Goldwyn Studios lot to see if they could "pass" as women. Then they tried using mirrors in public ladies rooms to fix their makeup, and when none of the women using it complained, they knew they could be convincing as women. There is a scene on the train recreating this moment.
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Jerry Lewis was offered the role of Jerry/Daphne but declined because he didn't want to dress in drag. When Jack Lemmon received an Oscar nomination for the role that Lewis gave up, Lewis claims he sent him chocolates every year to thank him and now regrets not taking the part.
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Georg Thomalla, who starred in the German original, Fanfaren der Liebe, dubbed Jack Lemmon in the German version of this movie.
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Porgy and Bess was being filmed right next to where the indoor scenes for this film were being shot. Sammy Davis Jr., Sidney Poitier and Dorothy Dandridge frequently visited the set.
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According to Jules Faith in "The Bronfmans", the only person who ever dared mock Lew Wasserman's "Music Corporation of America" was Billy Wilder in this movie. The musicians played by Tony Curtis and Jack Lemmon, looking for work, charge into an office labeled "Music Corporation of America". The only occupants are two frowzy women drinking gin.
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Marilyn Monroe recorded a vocal version for the theme to the film. It was to be played over the opening credits, but an instrumental overture took its place in the final version. The title track later appeared on an LP in the mid-'70s, with Marilyn's three other songs from the film.
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Jack Lemmon wrote that the first sneak preview had a bad reaction with many audience walkouts. Many studio personnel and agents offered advice to Billy Wilder on what scenes to reshoot, add and cut. Lemmon asked Wilder what he was going to do. Wilder responded: "Why, nothing. This is a very funny movie and I believe in it just as it is. Maybe this is the wrong neighborhood in which to have shown it. At any rate, I don't panic over one preview. It's a hell of a movie." Wilder held the next preview in the Westwood section of Los Angeles, and the audience stood up and cheered.
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In 2008, a Californian man who found a little black dress in his closet was stunned when appraisers for U.S. TV series Antiques Roadshow determined it once belonged to Marilyn Monroe. The frock - which Monroe was sewn into for Some Like It Hot - was estimated to be worth $250,000
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In the French post-synchronized version of the film, the actors are dubbed by: Claire Guibert (Marilyn Monroe); Jean-Claude Michel (Tony Curtis); Michel Roux (Jack Lemmon); Jean Martinelli (George Raft), Fred Pasquali (Joe E. Brown), Danièle Roy (Joan Shawlee) and Raymonde Devarennes (Barbara Drew).
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In the Italian post-synchronized version of the film, the actors are dubbed by: Rosetta Calavetta (Marilyn Monroe); Pino Locchi (Tony Curtis); Giuseppe Rinaldi (Jack Lemmon); Gualtiero De Angelis (George Raft); Giorgio Capecchi (Pat O'Brien); Carlo Romano (Joe E. Brown); Mario Pisu (Nehemiah Persoff); Lidia Simoneschi (Joan Shawlee); Manlio Busoni (Billy Gray); Cesare Polacco (George E. Stone); Bruno Persa (Dave Barry); Luigi Pavese (Mike Mazurki) and Massimo Turci (Edward G. Robinson Jr.).
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The last door Jerry and Joe open in the office building where they are looking for work says "Jules Stein, President" stenciled on the door. Jules Stein is a real person who founded the Music Corporation of America, also stenciled on the door. Billy Wilder played cards with Stein.
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Director Billy Wilder had originally planned to cast Mitzi Gaynor in the role of "Sugar Kane Kowalczyk", but when Marilyn Monroe became available, he used her instead.
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One of the few American movies ever given a "Condemned" rating by the Roman Catholic Legion of Decency.
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George Raft passes a young hood who is flipping a coin in his hand and he asked him where he learned a "cheap trick" like that. That trick was one of Raft's gimmicks in many of his earlier gangster movies.
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The character of Spats Colombo is in several ways reminiscent to the notorious Chicago gangster Al Capone. Capone was responsible for the Saint Valentine's Day massacre in 1929, in which his rival gang members were gunned down in a nearly identical fashion as shown in the film. The massacre occurred in a Chicago warehouse on Clark Street, which is also mentioned in the film.
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Spoilers 

The trivia items below may give away important plot points.

The movie's line "Well, nobody's perfect." was voted as the #48 movie quote by the American Film Institute (out of 100).
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According to George Raft, Marilyn Monroe suggested to Billy Wilder that he end the movie with Sugar and Spats tangoing off into the sunset. Wilder liked the idea, but decided on the ending with Osgood and Jerry.
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The now-famous closing line, "Nobody's perfect," was actually never intended to make the final film. It was apparently to be replaced by the writers once they thought of something they liked better. Furthermore, both I.A.L. Diamond and Billy Wilder credit the other for the genesis of the line.
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