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Guys and Dolls
Gambler Nathan Detroit seeks to organize an unlicensed craps game, but the police, led by Lieutenant Brannigan, are "putting on the heat." Nathan's usual locations are turning him away due to Brannigan's intimidating pressure. The Biltmore garage will allow Nathan to hold a game, but the owner requires a $1,000 security deposit, which Nathan does not have. Adding to his problems, Nathan's fiancée, Miss Adelaide, a nightclub singer, wants to get married after being engaged for fourteen years. She also wants him to go straight, but his only talent is organizing illegal gambling.
Nathan spots an old acquaintance, Sky Masterson, a gambler willing to bet on virtually anything and for high amounts. To win the $1,000 security deposit, Nathan bets Sky that he cannot take a girl of Nathan's choosing to dinner in Havana, Cuba. Nathan then nominates Sergeant Sarah Brown, a sister at the Save a Soul Mission, which opposes gambling.
Sky pretends to be a repentant gambler to meet Sarah. Sky proposes a bargain: He will recruit a dozen sinners into the Mission for her Thursday-night meeting if she will have dinner with him in Havana. With General Matilda Cartwright threatening to close the Mission's Broadway branch due to low attendance, Sarah agrees to the date.
Meanwhile, confident that he will win the bet, Nathan gathers all the gamblers, including a visitor that Harry the Horse has invited: Big Jule, a mobster. When Lieutenant Brannigan appears, Benny Southstreet claims they are celebrating Nathan marrying Adelaide. Nathan is shocked, but is forced to play along. Later, he realizes he has lost his bet and must marry Adelaide.
Over the course of their stay in Cuba, Sky and Sarah begin to fall in love. They return to Broadway at dawn and meet the Save a Soul Mission band, which has been parading all night on Sky's advice. Police sirens are heard, and the gamblers, led by Nathan Detroit, flee out through the back room of the empty Mission where they were holding a craps game.
The police arrive too late to make any arrests, but Lieutenant Brannigan finds Sarah and the other Save a Soul members being absent unlikely to be a coincidence and suspects Sky. Sarah is equally suspicious that Sky had something to do with the crap game at the Mission, and takes her leave of him, refusing to accept his denials.
Sky still has to make good on his arrangement with Sarah to provide sinners to the Mission. Sarah would rather forget the whole thing, but Uncle Arvide Abernathy warns Sky that "If you don't make that marker good, I'm going to buzz it all over town you're a welcher."
Nathan has continued the crap game in a sewer. With his revolver visible in its shoulder holster, Big Jule, who has lost all his money, forces Nathan to play against him while he cheats, cleaning Nathan out. Sky enters, knocks Big Jule down, and removes his pistol. Sky, who has been stung and devastated by Sarah's rejection, lies to Nathan that he lost the bet about taking her to Havana and pays Nathan the $1,000. Nathan tells Big Jule he now has money to play him again, but Harry the Horse says that Big Jule cannot play without cheating because "he cannot make a pass to save his soul." Sky overhears this, and the phrasing inspires him to make a bet: He will roll the dice, and if he loses, he will give all the other gamblers $1,000 each; if he wins, they are all to attend a prayer meeting at the Mission.
The Mission is near closing when the gamblers arrive, filling the room; Sky won the bet. They confess their sins, though with little repentance. Nicely-Nicely Johnson however, recalling a dream he had the night before, seems to have an authentic connection to the Mission's aim, and this satisfies everyone.
When Nathan tells Sarah that Sky lost the Cuba bet, which she knows he won, she hurries off to make up with him. There is eventually a double wedding in Times Square, with Sky marrying Sarah, and Nathan marrying Adelaide, while Nicely plays bass drum in the Mission's marching band.