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Three small-time gamblers, Nicely-Nicely Johnson, Benny Southstreet, and Rusty Charlie, emerge from the crowd and are arguing over which horse will win tomorrow's big race when the band members of the Save-a-Soul Mission, a local Salvation Army-like organization, pass by. Their leader, the pious and beautiful Sergeant Sarah Brown, begins a fervent street-corner sermon to all the passers-by, encouraging them to quit the evils of drinking, lying and especially gambling, and promoting a revival meeting at their mission the coming Thursday. Her message goes unheeded, and the Missionaries leave dejectedly.

Nicely and Benny run across Harry the Horse, a hoodlum out of Brooklyn, who is looking for some gambling action and wishes to know the location of the floating crap game run by Nicely's and Benny's employer, Nathan Detroit. As Harry leaves, Nicely and Benny are confronted by the local policeman, Lt. Brannigan. Nathan Detroit arrives and, after getting rid of Brannigan with a few well placed insults, bemoans his lot to his sidekicks. As a large number of "high-rollers" are in town, Nathan, who is broke, is pressured to find a place to hold his illegal game. But due to Brannigan's strong-armed police activity, he has found only one likely spot: the Biltmore Hotel garage. The owner's requirement, however, is a $1,000 security deposit.

Nicely suggests that Nathan borrow the money from Sky Masterson, a high-rolling gambler willing to bet on virtually anything. Nathan knows that Sky will not give money as a loan, but he will make a wager for that amount. As Nathan attempts to think of a bet he cannot lose, his fiancee Miss Adelaide enters on her way to lunch with some chorus girls from her nightclub act. She is overjoyed to see Nathan and presents him with a belt for the fourteenth anniversary of their engagement, which has no end in sight. This sad arrangement has given Adelaide a cold. Adelaide is unaware that Nathan is still running the crap game, so she must be fobbed off so Nathan can meet with Sky.

Nathan encounters Sky, who is only in town for a few days before he flies to Havana, Cuba, and attempts to draw him into a bet regarding the amount of cheesecake versus strudel sold at a nearby restaurant, which Nathan researched moments before. Sky sees through him and gives him a lecture his father had once told him about sucker bets. Nathan observes that Sky is traveling alone to Havana, and Sky brags that he could get any woman he wanted to accompany him, if he wanted to. Nathan then proposes a bet which he believes he cannot lose: Sky must take a doll (a woman) of Nathan's choice to dinner in Havana. Inspired by the passing Save-A-Soul Mission band, Nathan chooses none other than Sergeant Sarah Brown. Sky's confidence quickly fades.

At the mission, Sarah and her team, including her grandfather Arvide Abernathy, arrive out of breath and dejected. Sarah is frustrated that they have failed to recruit or save a single sinner in the time that they have been operating the Broadway mission. Sky enters the mission and proclaims that he wants to be saved. After Arvide leaves, Sky offers a proposal: He will fill the mission with "one dozen genuine sinners" for Sarah's Thursday revival meeting if she will accompany him to Havana the next night. He even offers her his "marker", a signed piece of paper reading "I owe you one dozen genuine sinners." His motives for coming to the mission now clear, Sarah rebuffs him. She tells him that he isn't the kind of man she wants and that she is waiting for the love of her life, whom she pictures to be a straight-shooting religious man she will know on sight. Sky reflects that he has not pictured the kind of girl he will marry, and that he plans on being surprised when he falls in love. He kisses her. After a moment, she slaps him, and he departs, promising to return the next day. He leaves his marker behind. She nearly tears it up, but thinks better of it and puts it in a drawer.

Nathan, certain that Sky will lose the bet, arranges to use the garage and then goes to the Hot Box, the seedy nightclub where Miss Adelaide is the headliner, and watches her farm-themed closing number. After the number, Adelaide confesses to Nathan that she has been lying to her mother for the past 14 years and has told her that she is married with a staggering five children. She asks him, for the umpteenth time, to go down to city hall and get a marriage license. When a loud-mouthed chorus girl lets slip that Nathan is running the crap game again, he makes a quick escape from Adelaide's wrath. She consults a medical book she has been reading, which tells her that the chronic cold she suffers is a psychosomatic reaction to her frustration with Nathan's failure to marry her.

The next day, Nicely and Benny observe that Sky is still following Sarah around, but getting nowhere, and that Nathan is running rings around himself to keep the crap game secret from Miss Adelaide and get back in her good graces. They comment on the power of a woman to make a man do anything she wants.

The band returns to their mission to discover that the formidable General Cartwright, the leader of their organization, has dropped by unexpectedly. The General sadly explains that due to the low turnout in Sarah's branch of the mission, she will be forced to close the branch unless there is some kind of turnout at the coming revival meeting. Sarah is pleading her case when Sky drops in, claiming to be a success case. Sarah opens a drawer, discovers Sky's marker, and haltingly promises to deliver "one dozen genuine sinners" on Thursday night.

A group of gamblers gathers at a newsstand, waiting to hear from Nathan the location of the game. Nathan, having sent Nicely to get the money from Sky, stalls for time, but the gamblers are growing anxious. Especially impatient is the high-roller Harry the Horse has brought from Chicago: Big Jule, a hulking thug armed with a snub-nosed revolver and a short temper. Things get worse when Lt. Brannigan arrives, suspicious of the large gathering of known lowlifes. Inspired by Adelaide, who is serendipitously passing by, Benny announces that the gathering is Nathan's "surprise bachelor party" and that he and Adelaide are finally getting married. Brannigan, satisfied, suggests that the couple elope, a suggestion the overjoyed Adelaide takes gladly. Nathan is perplexed but resigned to matrimony and Adelaide goes home to pack, promising to meet him after her show at the Hot Box the next afternoon. The danger past, the gamblers press Nathan again for the location of the game. He laments the fact that Sky's money hasn't arrived yet and Benny wonders if Sky took the doll to Havana after all. The Save-A-Soul Mission band passes, and Sarah is not in it; Nathan faints into Benny's arms.

In Havana, Sarah and Sky tour religious monuments and several nightclubs. Sky plies Sarah with a delicious "Cuban milkshake" called "Dulce de Leche", the secret ingredient of which is Bacardi rum, and she becomes increasingly tipsy, even starting a brawl when a dancer makes eyes at Sky. Sitting by a fountain, Sarah lets her hair down and proclaims that she is truly enjoying herself for the first time in her life. She kisses him, and Sky is surprised to find himself returning it, but can't bring himself to take advantage of Sarah while she's under the influence. He drags her back to the airport.

They return to New York, and Sarah, now sober, apologizes for her behavior. It is three or four o'clock in the morning, Sky's favorite time of the day, and he admits to Sarah that she is the only woman he has ever wanted to share it with. He asks her to call him by his real name: Obediah. Alone together on a quiet street outside the mission, Sarah and Sky each nervously confess their love and kiss. Unfortunately, their romantic moment is ruined when a siren rings out and a stream of gamblers run out of the mission, where Nathan, unable to secure the garage, has been holding the crap game. Sky tells Sarah he had nothing to do with this, but she tells him they are no good for each other. "What the hell kind of doll are you?" Sky exclaims in frustration. "I'm a Mission doll," she replies, and closes the door, leaving him standing outside in the cold.

That afternoon, Adelaide performs another song at the Hot Box, but Nathan isn't there. Sky is looking for him, and runs into Nicely, who is there bearing a message for Adelaide: Nathan cannot elope because his aunt is ill. He admits the truth to Sky: Nathan cannot elope because the game is still going on, nearly 24 hours after it began. Big Jule, having lost a bundle, has ensured that the game will continue until he comes out on top. Sky demands to be taken to the game, as he has some unfinished business to take care of before he leaves town. Adelaide appears, ready to elope with Nathan, and Nicely bumbles his message out and leaves. Adelaide is confused, but soon realizes that Nathan has stood her up yet again. Sky attempts to console her, telling her that people like Nathan and himself are not made for matrimony. He departs, leaving Adelaide to run back to her book for comfort.

Sarah and Arvide Abernathy are canvassing again. Sarah confesses that she loves Sky but resolves never to see him again, still blaming him for the previous night. Instead of scolding Sarah or condemning Sky, Abernathy expresses his faith in Sky's inherent goodness and urges Sarah to follow her hear. Sky and Nicely enter, and Sky tells Sarah he intends on making good on his marker. She coldly tells him to consider it paid and leaves, but Arvide subtly encourages him. Sky asks Nicely where the game is being held, and Nicely points down a sewer manhole.

The crap game is now being held in a sewer. The gamblers are hot, tired and running low on cash, but Big Jule and his revolver are insisting that the game continue until he can win back his heavy losses. To facilitate this, he insists on playing Nathan (who never actually gambles, rather taking his percentage of the top) with his "lucky dice". Big Jule's lucky dice have had the spots removed, allowing him to call them any way he wants. Nathan objects, but Big Jule forces him to bid higher and higher until he is cleaned out. Sky and Nicely enter, and Sky quickly puts an end to the cheating by knocking Big Jule out and relieving him of his gun. He asks the gamblers to attend the mission prayer meeting, but they refuse. Dejected, Sky starts to leave, but is stopped by Nathan, apologizing for not having the money to pay off his bet with Sky. Sky, however, gives Nathan $1,000, stating that he lost the bet, and Nathan won. Nathan uses this money to challenge Big Jule to an honest game, but is told by Harry the Horse that with honest dice Big Jule "cannot make a pass to save his soul." Inspired by this comment, Sky takes the biggest gamble of his life: Staking everything on a single roll of the dice, he bets every man at the game a thousand dollars against their souls. If he loses, everyone gets a thousand dollars each, but if he wins, they must all attend a prayer meeting at Sarah's mission. He tosses the dice.

Later, the gamblers head towards the mission, grumbling about attending the prayer meeting. On his way there, Nathan runs into Adelaide. He apologizes and she melts, asking him to elope right now. Nathan, remembering his promise, makes the unbelievable excuse that he has to attend a prayer meeting. Tired of his never-ending lies and excuses, Adelaide blows up and storms off .

At the mission, no sinners have come to be saved, and Sarah is just giving up hope when all of the gamblers shuffle in. Sky enters, makes sure everything is in order, and then hands the meeting over to Nathan. Nathan forces Benny, Big Jule, and Harry the Horse to give testimony, which rings rather hollow. When Brannigan bursts in, Nathan thinks fast and piously asks Nicely to get up and testify. Nicely invents a dream which encouraged him to repent, and quickly gets the crowd on their feet. Brannigan cuts through the religious fervor, by threatening to arrest everyone for the crap game in the Mission the previous night, but Sarah clears them, saying she has never seen them before in her life and so they couldn't have been there. After Brannigan leaves, Nathan confesses in his testimony that they did indeed hold the crap game in the mission, and also confesses the bet he made with Sky about taking Sarah to Havana. He adds that he won the bet, to Sarah's shock, and she realizes how much Sky actually cares for her. She slips out as the meeting continues.

Sarah and Adelaide serendipitously run into each other, and Adelaide is shocked and delighted to discover that Nathan actually attended a prayer meeting and wasn't lying, though this of course just increases her confusion. They commiserate in their woes, and then resolve to accept their men as they are, since they can always change them later.

Several weeks later, many changes have happened in Times Square. Nathan has opened a newsstand and is finally marrying Adelaide now that he has gone (almost) straight. He has, however, forgotten to get a location to hold the wedding. The problem is unexpectedly solved when the mission band marches by, with none other than Sky Masterson beating the big bass drum. Arvide has just married Sky and Sarah, and is more than happy to provide the same service to Nathan and Adelaide. All ends happily, even if Nathan appears to have caught Adelaide's cold at the thought of matrimony

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