Directed by Bill Wilder, two broke musicians witness the Valentine’s Day massacre and join a women’s orchestra going to Florida.
At night four men ride in a hearse with a coffin. They hear sirens and accelerate. Police shoot at the hearse, and the men take rifles from the ceiling of the hearse and shoot back. The police car stops, and the hearse gets away. They open the coffin and see bottles leaking from the bullets.
The four men take the coffin out of the hearse and carry it into a funeral parlor. A police car arrives, and six policemen get out. Detective Mulligan (Pat O’Brien) gets out of a car and asks Johnny who runs the joint and what the password is. Mulligan asks a police officer to give him five minutes and then hit them with everything.
Mulligan comes in and says he is a pallbearer for the funeral. They let him into a speakeasy with hot music and dancing chorus girls. Mulligan sits at a table and orders a drink. Spats Columbo (George Raft) comes in, and a drunk man spills liquor on his spats. His men remove the man. Columbo sits down with three men at a reserved table. Mulligan tells the waiter the place may be raided. In the band Joe (Tony Curtis) is playing the saxophone, and Jerry (Jack Lemmon) is playing a base fiddle. Jerry asks Joe if they get paid tonight. Joe says they owe back rent and the girls in the line. Joe wants to bet on a dog at 10-1. Jerry asks what happens if he loses. Jerry sees Mulligan put on his police badge. Mulligan looks at his watch, and the police break in and make arrests. Jerry and Joe leave with their instruments. Mulligan tells Columbo he and his men are under arrest for owning the joint that dispenses alcohol. They are all drinking buttermilk. Columbo says the four men are his lawyers from Harvard.
Outside Joe and Jerry go down the fire escape. Jerry says they are going to be locked out. Joe considers pawning their overcoats. Jerry disagrees.
The next day in a cold wind Joe and Jerry carry their instruments without overcoats. Jerry says he can’t go on. Joe wants to bet again and asks Jerry to hawk his bass. Joe asks if there are any jobs. Nellie (Barbara Drew) tells Joe to wait, and he kisses her. Jerry says they are desperate. She says someone in Florida wants a sax and a bass for three weeks. In the inner office Sig Poliakoff (Billy Gray) is trying to find the musicians. Joe and Jerry come in and ask him for the Florida job. He calls William Morris and says they have to be under 25 and female. Jerry says they can do it by borrowing clothes and using wigs. Sig tells them about a Valentine’s dance at the University of Illinois. Joe wants to do it for the $12, but Jerry says it is a hundred miles. Joe asks Nellie what she is doing tonight and wants to borrow her car.
On a cold night Jerry tells Joe they could have been in Florida. They walk into a garage, and six men pull guns on them. Joe says they came for Nellie’s car. Joe asks the man to put gas in the car. A car drives in, and four men get out with machine guns and make the six men face the wall. Joe and Jerry hide. The attendant is made to join the others. Columbo speaks to Charlie about recommending his mortuary to his friends. Columbo says goodbye, and his men kill the seven men. Columbo tells Joe and Jerry to come out. Columbo tells them they are not going anywhere. Charlie tries to pick up the telephone and is shot. Joe and Jerry run out of the garage. Columbo and his men get in the car and drive off. Joe and Jerry go into a cigar store. Joe tells Jerry they have to shave their legs. Joe, using a feminine voice, calls the man looking for girl musicians.
Joe and Jerry are dressed as women and wear make-up, and Jerry asks how they keep their balance in high heels. Joe says his name is Josephine. They see Sugar Cane Kowalczyk (Marilyn Monroe) walking by the train. Jerry is amazed at how she moves. Joe says he does not have to have a baby. A newspaper boy announces the news of the massacre. Joe tells the manager Sweet Sue (Joan Shawlee) they went to a conservatory and are to join the band. Jerry says his name is Daphne, and they board the train. They introduce themselves to the women musicians. Jerry tells Joe that he tore off one of his chests, and they go into the Women’s room. They see Sugar Kane drinking from a flask, and she asks them not to tell anyone. She introduces herself and says she sings. She says most of them are running away. She does not want to stop drinking and puts the flask under her garter.
The women rehearse in a car, and Sweet Sue tells the two to goose it up a little. She asks about the holes in the base. They play hot music. Sugar Kane sings, “Runnin’ Wild.” Sweet Sue and Beinstock (Dave Barry) find the flask, and he warns Sugar Kane again. Jerry asks for her flask. Sweet Sue says she will not put up with liquor or with men. Jerry says men only want one thing from girls. They play music, and Sugar Kane smiles at Jerry.
On the train Jerry is watching the half-dressed women. Joe reminds Jerry that he is a girl. He says goodnight to Sugar. Sweet Sue asks Beinstock if there is something funny about those two; she can feel it. Joe and Jerry say goodnight. Sugar Kane gets out of her bunk and goes to see Daphne to thank her. She asks what she can do for her, and she gets in the bunk as Sweet Sue walks past. Sugar Kane asks to stay there until she goes back to sleep. Sugar Kane says her head is hot, but her feet are cold. Jerry reminds himself he is a girl. He recommends whiskey and reaches down below to get a bottle out of a suitcase. He falls on the floor and hands her the bottle. He gets two cups and joins her in his bunk. She pours it, and he says it may be a surprise party. Another woman wants to join them, and she tells another woman about the party. Word spreads, and women climb into the bunk. A woman asks Joe for cherries, and he sees legs hanging down from above. He tries to break up the party, and Jerry tells them all to get out. Sugar Kane gets a block of ice, and Joe takes it to a sink. She chips at the ice, and they talk. She says she cannot trust herself with men, especially saxophone players. She says men bet on horses, and she keeps having the same problem. A woman comes in and takes a tray of ice away. Sugar Kane says Florida has millionaires, and she is going to catch one. She wants a man with glasses who is gentle. Joe wishes her well.
Jerry drinks and talks with the women in his bunk. Ice goes down inside his nightgown, and they tickle him so much that he pulls the emergency brake. The women fall on the floor and go back to their bunks. Sweet Sue comes in and asks what is going on.
In Florida a bus takes them to a fancy hotel on the beach. Old men sitting and reading notice the women arriving. Joe tells Sugar Kane those are the millionaires. Osgood Fielding III (Joe E. Brown) notices Jerry who loses a shoe. He picks it up for her and puts it back on. He carries her bags. He says he invests in showgirls and is staying on his yacht. He asks her to dinner, and Jerry says he will be playing the bow fiddle. Jerry takes the bags, and they both get in the elevator. The door opens, and Jerry slaps Osgood.
Sweet Sue announces the roommates and room numbers. Joe talks with Sugar Cane who tells about a past sax player. Joe says she will meet a young one. A bellboy tries to make a date with Joe and goes out. Jerry comes in and says he got pinched in the elevator. Jerry takes off his wig. Joe says that Spats is looking for them. Joe says they have a good situation. Jerry says Joe is after Sugar. Joe says they are like sisters. They hear a knock, and Jerry puts on the wig. Beinstock comes in and asks where his bag and glasses are. Sugar Kane comes in, and he goes out. She asks for her ukulele, and Jerry hands it to her. Sugar asks them to go swimming with the girls. She says they don’t need a bathing suit. Jerry goes out with Sugar. Joe locks the door and opens a suitcase and finds men’s clothes and Beinstock’s glasses.
The women in bathing suits are swimming in the ocean. Joe is dressed as a yachtsman with glasses. Sugar says Daphne is a big girl. Joe gets rid of a kid and sits on a chair. Women play with a ball, and Joe trips Sugar who is chasing it. He says people usually sue him for a million dollars. She asks who he is. He is reading the Wall Street Journal. She asks where she has seen him, and he says it could have been in Vanity Fair. He says his yacht puts up a flag for cocktails. He says he is not married. He asks about her, and she admits she plays jazz. He likes classical music, and she does too. They both pretend to be from high society and are bored with it. She invites him to come to the hotel. He says he only comes ashore twice a day. He implies his family owns the Shell Oil Company. Jerry recognizes Joe, who tells him to move along. Joe warns Jerry not to squeal on a roommate. Sugar pulls Daphne away and says she saw him first. Jerry suggests they go tell Josephine, and they run up to the room.
In the room Jerry tells Sugar to wait for her. They find her in the bathtub singing. Sugar says she met a rich man, and she tells about him. Sugar’s roommate comes in and asks her for the key. They leave, and Jerry scolds Joe who stands up in the bath in his clothes. Joe grabs Jerry’s shirt, and the phone rings. Joe answers it. Osgood is calling Daphne from his yacht and invites her there after the show. Joe finds out there will be no crew there tonight. Joe tells Jerry that he is invited to Osgood’s yacht. Jerry says he is not going, but Joe says he is going there with Sugar while Jerry is with Osgood on shore.
The band plays as Sugar Kane sings, “I Wanna Be Loved by You.” Osgood waves to Jerry, who complains Joe talked him into something. He wonders how to keep him on shore. The bellboy brings flowers from Osgood, and he gives one to Joe, who puts a card on the bouquet. Sugar asks Joe if her millionaire forgot, and he gives her the card. She says he is taking her on the yacht. Sweet Sue says goodnight and intends to keep her girls virtuosos. Joe runs off stage and up to the room. He changes into the yachtsman clothes and goes out the window and climbs down.
Sugar Kane runs outside. Joe gets on a bicycle. Osgood talks with Jerry, and Joe goes by on the bike. Osgood suggests they tango, and they walk together. Sugar Kane runs to the beach, and Joe follows her on the bike. He puts the bike under the dock and gets in a motor boat. Sugar hears him and gets in the boat. He manages to start the boat’s engine and goes in reverse out to the yacht. He shows her around the yacht, and she finds a good room. He opens champagne, and they drink. They sit on a couch and talk. He says it is the crew’s night off. She says she has never been alone with a man at night in the middle of the ocean. He says he is harmless because girls leave him cold. She asks if he has tried, and he kisses her. He says it was nothing for him. He says he cannot fall in love anymore. He tells her about a girl in college, but she died in the Grand Canyon. Now he no longer has feelings. He eats chicken, and she kisses him. He does not react, and she says he should see a doctor. He says he has seen many doctors. He says if he found a girl who could help him, he would marry her. She kisses him again. She turns out the lights and plays the radio. He drinks from both glasses, and she tells him not to fight it and relax. She kisses him again, and he shakes his head.
Jerry and Osgood are tangoing, and he says she is leading again.
Sugar is kissing Joe, and he says he is not sure and asks for more. He says he is feeling something in his toes. She says his glasses are steaming up. He says he never knew it could be like that. He asks her where she learned to kiss, and she says for the Milk Fund. He says he will send them a check.
Joe takes Sugar in the motor boat back to the dock. They pass drunk Osgood who drives the boat. Joe and Sugar walk back to the hotel, and he says goodnight, kissing her again. She kisses him back and goes in the hotel. He climbs up and comes back in the window. Jerry is laying on the bed in a good mood. Jerry says he is engaged to Osgood. Joe says he can’t marry him. Jerry wants to marry him for security, and he knows there is a problem. His mother must approve, and they will have to agree on a honeymoon. Jerry will tell him after the ceremony, and it will be annulled. He will get alimony. Joe tells him to forget that and to tell himself that he is a boy. Jerry shows him the diamond bracelet Osgood gave him, and Joe suggests they keep it. Sugar Kane knocks, and Joe hides in bed. Jerry lets her in, and she lies on the other bed. She learns that Daphne got a proposal. The bellboy comes in to see Joe.
Spats Columbo and his four men arrive at the hotel, and Mulligan is watching them. A man gives Spats orders from Little Bonaparte. He and the other men are searched, and guns are found. Mulligan talks to Columbo and asks where he was on Valentine’s Day. Mulligan says his spats had blood on them. Mulligan says they are looking for the witnesses, and Columbo implies they are dead. Jerry and Joe are dolled up, and Jerry sees the gangsters. They go in the elevator and are joined by Columbo and his men. Jerry says they would not be caught dead in Chicago.
In their room Joe and Jerry pack their bags. Jerry says they can sell the bracelet and go to South America. Joe calls Sugar, and Jerry says they have to go. Joe tells Sugar he did not sleep well, and she tells about her dream with him. He says he can’t meet her tonight because he is sailing right away. He has to go because of a merger. He wishes to do something for her and puts the bracelet in a flower box for her, which he shoves to her door. She gets the orchids and finds the diamond bracelet. He says it is a going-away present. Jerry returns, and Joe says goodbye to her. Jerry asks what happened to his bracelet, and Joe says it is on the level. Sugar walks in and looks for the bourbon. Joe gives her a hot water bottle, and Jerry asks where she got the bracelet. He advises her to throw it in his face. She is crying and goes out. Jerry says they have to get away from the mobsters. Joe leads him out the window.
Columbo has a man button his spats. He says that Little Bonaparte is getting tired and should retire. They see Joe and Jerry climbing down, and Columbo says maybe they are not dames. He gets the bass and sees the bullet holes. They realize who they are and go out. Joe and Jerry climb in the window. In the hall they see a man in a wheelchair and go in his room.
Jerry as a bellboy wheels Joe out of the elevator, and the gangsters chase them. They run into a banquet room and hide under the table. People come in, and the gangsters sit down. They plan to get them after the banquet. Little Napoleon (Nehemiah Persoff) and his six men come in. He speaks as president of the organization and says they made $112 million and paid no taxes. They have a moment of silence for those who have been rubbed out. He tells Spats and his men to bow their heads too.
A man gets inside a large cake in the kitchen. Napoleon says he is retiring and talks about Spats. He says letting witnesses get away was careless. Columbo says he almost caught them today. Napoleon says they baked a cake for him. They sing, “For he’s a jolly good fellow.” The cake is wheeled in, and a man pops out with a machine gun, shooting Columbo and his men. Joe and Jerry make a run for it, and Napoleon sends men after them. Mulligan comes in and asks what happened. He speaks into Napoleon’s hearing aid.
Joe and Jerry come out of the elevator dressed as women. Joe tells Jerry to call Osgood and elope. Joe hears Sugar singing, “I’m Through with Love” and goes into that room. Joe goes up to her and kisses her, and she recognizes him. He runs away from the gangsters, and she realizes he loves her. Jerry and Joe run through the halls and hide under a covered cart.
Joe and Jerry run to the dock, see Osgood, and get in his motor boat. Sugar arrives on the bike and gets in the boat too. Osgood drives the boat, and Joe tells Sugar she does not want him. She puts her arms around and dares him to talk her out of it. Jerry gives excuses as to why he can’t marry Osgood. He does not care about her reasons. Finally Jerry takes off his wig and says he is a man, but Osgood says, “Nobody’s perfect.”
This original comedy satirizes the bootleg era with its gangsters and creates funny situations with the men pretending to be women while excited by the sexy Sugar Kane.