Joe and Jerry run out into the cold winter night as sirens blare. Jerry is disturbed by what they just saw, and Joe urges him that they have to get moving or they will be killed. The two musicians run down the street as a speeding cop car drives past. Finding shelter in a nearby cigar store, Joe grabs a nearby payphone to make a call, but Jerry is anxious that they should get out of town as soon as possible. Joe agrees, assuring Jerry that they are going to have to shave their legs before they do. Jerry is confused as Joe gets through to Sid, affecting the voice of a woman and accepting the Florida all-girl band job. The scene shifts and we see Joe and Jerry walking down a train platform dressed as women. As they walk towards the train door, Jerry complains about how uncomfortable the high heels are and that wearing a dress feels “drafty.” Joe and Jerry wait in line to get on the train, with Jerry complaining that they will never get away with it.
Suddenly, a beautiful woman begins walking towards the train as scratchy seductive trumpet music plays. As she walks towards the train door, waves of steam burst out of the side of the train, as though the train itself is attracted to her. “I tell you, it’s a whole different sex!” Jerry exclaims, and Joe scolds him, assuring him, “Nobody’s asking you to have a baby” and detailing that once they get to Florida, they will abandon the drag. As Jerry begins to have second thoughts about the plan, a newspaper boy walks by carrying a newspaper detailing the bloody event at the garage, and Jerry abruptly agrees that they ought to go to Florida. They go to get on the train. At the train door they run into the manager, Mr. Bienstock, and the woman from Sid’s office, who introduces herself as Sweet Sue. Joe introduces himself as “Josephine,” and Jerry introduces himself as “Daphne.” Sweet Sue asks them where they have played before, and they struggle to piece together a backstory, with Joe finally telling her they went to a conservatory. Bienstock tells them which train car they are in and they climb aboard.
On the train, Joe confronts Jerry about saying his name was Daphne, and Jerry tells him, “Well, I never did like the name Geraldine.” Entering a compartment filled with chattering women, Jerry yells, “I’m the bass player, just call me Daphne!” and the women greet him energetically. Joe introduces himself as Josephine and is greeted in kind. Jerry then sits down next to a woman and begins waxing poetic about his seamstress until Joe ushers him along. When another woman tries to tell Jerry/Daphne a joke, he wants to hear it, but Joe/Josephine tells her they don’t want to hear the joke. Mockingly, Bienstock tells the girl who tried to tell them the joke, “They went to a conservatory!” and everyone rolls their eyes and laugh. Alone, Jerry relishes the fact that they are on a train full of beautiful women, but Joe urges him to hold back. In a struggle between the two friends, Joe accidentally pulls off one of Jerry’s fake breasts, and Jerry insists that Joe come and help him reattach it. Jerry tries to go into the Men’s Room, but Joe pulls him into the Women’s Room.
In the room, the two men run into the beautiful bombshell that they saw on the platform. She takes a swig of alcohol from a flask as seductive trumpet music plays, then stands abruptly when she realizes that she has company. She tells them that she thought they were Sweet Sue, and asks them to promise not to tell anyone that they saw her drinking, because “if they catch me one more time, they’re gonna kick me out of the band.” They introduce themselves to the woman, and she introduces herself as Sugar Kane. She tells them more about herself, saying that her mother was a piano teacher and her father was a conductor. Sugar Kane then tells them that she also sings and plays the ukulele, that she’s not a very good singer, but that she’s running away. When Daphne and Josephine ask her what she’s running away from, she deflects, but offers them some bourbon. “I don’t want you to think I’m a drinker. I can stop anytime I want to, except I don’t want to, especially when I’m blue,” she says. She then tells them she’s always getting caught, even though all the girls in the band drink, before putting her flask in her garter and leaving the Women’s Room. Joe and Jerry are both instantly attracted to Sugar, but Joe tries to calm Jerry down, as he is especially smitten.
The train makes its way towards Florida and we see the band practicing in one of the cars. Sweet Sue looks at the band with a perplexed expression on her face as Joe takes a solo on the saxophone. All of a sudden Sweet Sue stops the band and tells Joe that he’s playing poorly and to “goose it up a little!” He hesitantly agrees, when Sweet Sue notices a number of bullet holes in Jerry’s bass. “How did those get there?” she asks, but Jerry giggles and feigns ignorance. The band plays again. Joe and Jerry get very into the song, with Jerry spinning his bass around throughout. Sugar Kane begins singing, dancing provocatively, and playing her ukulele. Her performance delights and distracts Jerry and Joe, as she shakes and shimmies her way through the song. By the end, Sugar’s flask has fallen out of her garter, which makes Sweet Sue scream and call Bienstock over. He picks up the flask and asks whose it is, and when no one speaks up, he assumes that it is Sugar’s.
To save her from being fired, Jerry tells Bienstock that it’s actually his flask. Sweet Sue admonishes “Daphne” and “Josephine,” telling them that the two things they don’t tolerate in the band are liquor and men. Jerry and Joe are indignant, with Jerry insisting, “Men!…We wouldn’t be caught dead with men. Rough, hairy beasts with eight hands! And they all just want one thing from a girl!” Bienstock takes offense to this insinuation, and Sweet Sue taps her baton to have them do the song again. Sugar smiles and laughs at Jerry, and he is clearly delighted. The scene shifts to the girls’ sleeping car on the train, with girls laughing and socializing in varying states of undress. Jerry watches them, delighted, from his sleeping compartment. The girls wish goodnight to “Daphne” as they climb into bed. Jerry calls out goodnight to Sugar, who calls her “honey” and climbs into bed. Joe takes the ladder off of Jerry’s bed in hopes of preventing him from climbing down and getting into any funny business in the night.
Observing the two men arguing, Sweet Sue turns to Bienstock and notes that there’s “something funny about those two girls.” Bienstock doesn’t know what she means, but Sweet Sue tells him that she just gets a feeling in her stomach. Bienstock tells Sweet Sue that he will keep an eye on them and shuts off the lights for bed. As he falls asleep, Jerry whispers to himself, “I’m a girl” over and over again. The train chugs on, and in the middle of the night when everyone has gone to sleep, Sugar climbs out of her bed in a black negligee, and tiptoes down the hall, and climbing up a ladder into Jerry’s bed. When she wakes Jerry up, he is immediately startled, and she thanks him for helping her cover up the flask incident earlier. “I just thought that us girls should stick together!” he tells her. Sugar then offers to do a favor for Jerry in the future, before abruptly jumping into the compartment and shushing him. Sweet Sue is roaming the halls, and walks past the compartment on her way to the bathroom.
“I don’t want her to know we’re in cahoots,” Sugar whispers to Jerry, and Jerry tells her that she won’t tell anyone, not even “Josephine.” Sugar then tells Jerry that she’s going to stay in his bed for awhile, which he welcomes. As Sugar continues to confide in Jerry, thinking that he is “Daphne,” a trustworthy woman, he giggles anxiously. Sensing Jerry’s anxiety, Sugar feels his forehead, and then rubs his feet with hers to warm them up. After Jerry tells her, “I’m a very sick girl,” Sugar goes to leave, fearing she will catch the sickness, but Jerry insists that she stay and that they have a shot of whiskey. “I know where to get it!” he tells her, before hanging his body out the window of the compartment and into Joe’s compartment, where he reaches into a pocket for the flask. In all his rummaging, he starts to wakes Joe up, who stirs for a moment before rolling over. Still hanging outside Joe’s compartment, Jerry tells Sugar to pull him back up into his own compartment, but he is too heavy and she drops him with a thud on the hallway below. Sugar tells Jerry to get some cups, which he does from the end of the hall. As he climbs back into his compartment, one of the girls in the band pokes her head out and makes a curious expression.
Back in the compartment, Sugar tells Jerry to turn on the light so she doesn’t spill the bourbon, but he tells her that they shouldn’t risk revealing their private party. “This may even turn out to be a surprise party!” Jerry says, alluding to potentially revealing his actual sex. Just then, the girl who spied Jerry climbing into bed pops her head in, smiling, asking if the party is private. Sugar asks the girl, whose name is Dolores, if she still has the bottle of vermouth, and Dolores tells her she does and goes to fetch it so they can make Manhattans. Jerry is disappointed that they’ve been interrupted. In the hallway, Dolores runs into another girl, whom she tells about the party. The girl excitedly gets some cheese and crackers, as more and more girls begin poking their heads out and getting excited about the party. Pretty soon, almost all the girls are out of their beds and climbing up to Jerry’s. Jerry gets angry, insisting that it’s a private party, but more and more girls pile in. The girls begin eating and drinking voraciously, all to Jerry’s chagrin. One of the girls pops into Joe’s compartment and asks him if he has any cherries, and he soon sees the girls going up to Jerry’s bunk. He calls to Jerry, who pops out and tells Joe that he didn’t invite the girls. Sugar climbs out of the bunk, which makes Jerry even more upset. She goes and gets a huge block of ice and hands it to Joe, beckoning him to bring it over so they can break it up. He follows her into another car.
While Jerry was willing to take the job in drag and go to Florida from the beginning, it is not until they are being chased by one of the most powerful mobsters in Chicago that Joe sees the option of donning women’s clothes as viable. As soon as Spats Columbo is on their trail, Joe makes the call and within the hour the bumbling friends are wearing dresses, lipstick, and heels. These circumstances—the fact that the two naive musicians have witnessed bloody murder and are now wanted dead by some of the most cold-blooded killers around—increases the comic stakes of the drag. Donning drag is not only for a job or just for fun: it is their only chance to get out of town and start a new life. The image of two masculine men affecting the feminine comportment of two women is a humorous sight, especially when either of them break character to commiserate about the treachery of heels and dresses.
The comedy of Joe and Jerry’s situation is only heightened by the presence of a bunch of beautiful blonde band members running around in their underwear, and more particularly by the arrival of Sugar Kane. In contrast to Joe and Jerry, two straight men pretending to be women, she is undeniably womanly, an almost prototypical feminine specimen who feels no discomfort in heels and a dress. As she arrives at the train, seductive trumpet music plays and she slinks towards the train with a loose-hipped gait. She oozes sensuality and feminine charm, which strikes a humorous contrast with Joe and Jerry. Adding to the comedy of her arrival in the film is the fact that both the men are immediately attracted to her. Following through on their attraction for her, however, would require that they either pose as lesbian women or reveal themselves to be cross-dressing men. Both revelations put them outside of the dominant male culture of which they belong, complicating their positions as straight men in an all-female band in humorous ways.
Another element of the humor of the film is the fact that while Jerry is initially unsure about their plan to don drag, he quickly takes to the character. While Joe just wants to use easy female nicknames, when they introduce themselves to Bienstock and Sweet Sue, Jerry excitedly tells them that his name is “Daphne” and later explains to Joe that he never liked the name “Geraldine,” which shows that he is more invested in the fiction of them being females than he had initially let on. Then, when they meet the other girls in the band, Jerry gets lost in the character of Daphne and begins telling one of the girls about his seamstress, spinning a highly developed story about where he gets his clothes. Jerry’s ease with his female character is funny because it marks him as having feminine inclinations that he has previously had to keep under wraps. The character of Daphne is a fundamentally liberating part for Jerry, which differentiates him from Joe even more.
The scenario is ripe for comedy. In barely believable drag, two lowlife musician types try to hide their identities from a prying band manager and bandleader, while playing in a band filled with gorgeous blonde girls. While Jerry had initially seemed more skeptical of the plan than Joe, he soon becomes excited by the prospect of being surrounded by beautiful women, to the extent that he can barely contain himself and must keep reminding himself that he is not supposed to blow his cover. His mantra, “I’m a girl,” gets repeated to humorous effect as he finds himself in more and more sexually tempting scenarios. While his appearance as a woman is warm and matronly, the performance of “Daphne” obscures his baser instincts, a tension that he can barely keep ahold of.
Making Jerry’s task of keeping it cool all the more difficult is the naively seductive power of Sugar Kane, played breathily by the ultimate pin-up, Marilyn Monroe. Jack Lemmon, Tony Curtis, and Marilyn Monroe play each of their roles to great comic effect. Monroe’s performance is exceedingly ditzy, as she smiles and giggles and breathily thanks Jerry for his kindness, remaining impressively clueless about his actual sex. When she climbs into bed with Jerry, she treats it as a veritable slumber party with her older friend “Daphne,” recounting the fun she had as a child snuggling up in bed with her sister. Monroe bubbles over with innocent giggles and a raw charm that only serves to seduce Jerry more. Sugar’s ignorance of the fact that Jerry is a man emboldens her to be less self-conscious and more honest with him, which heightens the stakes and the comedy. While Jerry’s desire for her teeters on the edge of becoming uncouth, Jack Lemmon maintains an innocent charm himself, which keeps the character humorous, rather than explicitly creepy.