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.
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.
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.
Marilyn Monroe was pregnant during the filming, as a result she looked considerably heavier. She had 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.
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!"
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.
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.
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.
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.
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.
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.
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 (1997) determined it once belonged to Marilyn Monroe. The frock - which Monroe was sewn into for Some Like It Hot (1959) - was estimated to be worth $250,000
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.
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."
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 occupant is a woman sitting at a desk, drinking from a bottle.
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.
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.
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.
The Nehemiah Persoff role originally was offered to Edward G. Robinson, but Robinson had vowed never again to work with George Raft, with whom he had a fist fight on the set of 1941's "Manpower" when for a scene Raft spun him around too hard. However, the role of Johnny Paradise, the kid homaging Raft's "cheap trick" of coin-flipping, is also the man with the Tommy gun in the birthday cake who mows down Spats and his gang. The actor is Edward G. Robinson Jr.
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.
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.
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. I.A.L. Diamond and Billy Wilder each credit the other for the genesis of the line. Wilder later fashioned his own epitaph with the similar line: "I'm a writer, but then nobody's perfect."