Plot

In New York, a gambler is challenged to take a cold female missionary to Havana, but they fall for each other, and the bet has a hidden motive to finance a crap game.

All the hot gamblers are in town, and they're all depending on Nathan Detroit to set up this week's incarnation of "The Oldest Established Permanent Floating Crap Game in New York;" the only problem is, he needs $1000 to get the place. Throw in Sarah Brown, who's short on sinners at the mission she runs; Sky Masterson, who accepts Nathan's $1000 bet that he can't get Sarah Brown to go with him to Havana; Miss Adelaide, who wants Nathan to marry her; Police Lieutenant Brannigan, who always seems to appear at the wrong time; and the music/lyrics of Frank Loesser, and you've got quite a musical. Includes the songs: "Fugue for Tinhorns," "Luck Be a Lady," "Sit Down, You're Rocking the Boat."—Syam Gadde <gadde@cs.duke.edu>

In New York, the smalltime gambler Nathan Detroit has been eloping from getting married with his girlfriend Adelaide for fourteen years. Nathan needs one thousand dollars in advance to rent a place for the crap game but neither he nor his friends Nicely-Nicely Johnson and Benny Southstreet can afford. Nathan decides to bet against the gambler Sky Masterson, challenging him to have a dinner in Havana with a woman of his choice. Sky accepts the bet and Nathan chooses the prude Sergeant Sarah Brown, who runs a mission for sinners. Sky visits Sarah and invites her to have dinner with him in Havana; in return, he would bring one dozen sinners to the mission. Sarah refuses the deal, but when General Cartwright comes to New York to shutdown the mission, Sarah feels that the only chance to keep the mission operating is accepting Sky's invitation. They travel to Havana and fall in love with each other; but when they return to the mission, Sarah discovers that Nathan used the place for his crap game. Further, she believes that Sky has plotted the scheme to use her. Now Sky has to convince the gamblers and gangsters that arrived in New York to the crap game that they should go to the mission to help Sarah.—Claudio Carvalho, Rio de Janeiro, Brazil

Every gambler in New York - and many from out of town - is waiting for Nathan Detroit to announce the location of his big craps game. There's only one problem: Detroit doesn't have the $1000 he needs to get the game going. When he sees gambler Sky Masterson he bets a $1000 that Masterson couldn't convince a girl of Detroit's choosing to go with him to Havana in the next 24 hours. Masterson accepts and Detroit chooses Sarah Brown, a Sergeant in the Salvation Army as the girl. Undaunted, Masterson sets out to seduce Sarah and get her to Havana. As far as Detroit is concerned, he's made a bet he can't lose. While Masterson woos Sarah, Detroit has to deal with his girlfriend of 14 years who has decided it's time they should get married.—garykmcd

Gambler Nathan Detroit (Frank Sinatra) is under pressure from all sides: he has to organize an unlicensed craps game but the police, led by Lieutenant Brannigan (Robert Keith), are "putting on the heat". All the places where Nathan usually holds his games refuse him entry due to Brannigan's intimidating pressure. The owner of the Biltmore garage does agree to host the game provided Nathan pays him $1000 in cash in advance. The garage owner will not even accept a "marker" or IOU, he insists on having the money itself before the game can be held.

Adding to Nathan's problems, his fiancée, Miss Adelaide (Vivian Blaine), a nightclub singer, wants to bring an end to their 14-year engagement and actually tie the knot. She also wants him to go straight, but organizing illegal gambling is the only thing he's good at.

Trying to obtain the money for the garage, Nathan meets an old acquaintance, Sky Masterson (Marlon Brando), a gambler willing to bet on virtually anything and for high amounts. Nathan proposes a $1000 bet by which Sky must take a girl of Nathan's choosing to dinner in Havana, Cuba. The bet seems impossible for Sky to win when Nathan nominates Sergeant Sarah Brown (Jean Simmons), a straight-walking official of the Save-a-Soul Mission (based on the Salvation Army) which opposes gambling.

Sarah herself has problems. She has been in charge of the Broadway branch of the Mission for some time now and no drunks or gamblers have come in to confess or reform. To approach Sarah, Sky makes out that he is a gambler who wants to change. Sarah knows of his reputation and is suspicious: "It's just so unusual for a successful sinner to be unhappy about sin."

Hearing that Sarah's superiors are threatening to close down the Mission in order to concentrate their activities in other places, Sky suggests a bargain: he will get a dozen sinners into the Mission in return for her having dinner with him in Havana. With little choice left, Sarah agrees.

Confident of his victory, Nathan has gathered together all the gamblers, among whom is Big Jule (B.S. Pully), a Chicago mobster. When Lieutenant Brannigan appears and notices this gathering of "senior delinquents", Nathan's sidekick, Benny Southstreet (Johnny Silver) covers by claiming that they are celebrating the fact that Nathan is getting married to Adelaide; Nathan is shocked by this, but is forced to play along. Later, when he sees the Save-a-Soul Mission band passing by and that Sarah is not among them, he collapses on the realization that he has lost the bet with Sky. He has no money and nowhere to play the game and he is now committed to actually marrying Adelaide. (Nathan does love Adelaide but is rather uneasy about going straight, either maritally or lawfully.)

Over the course of their short stay in Cuba, Sky manages to break down Sarah's social inhibitions, and they begin to fall in love with one another. He even confesses that the whole thing was part of a bet but she forgives him as she realizes that his love for her is sincere.

They return to Broadway at dawn and meet the Save-a-Soul Mission band which, on Sky's advice, has been parading all night. At that moment police sirens can be heard and, before they know it, the gamblers led by Nathan Detroit are hurrying out of a back room of the Mission, where they took advantage of the empty premises to hold the game.

The police arrive too late to make any arrests but Lieutenant Brannigan finds the absence of Sarah and the other Save-a-Soul members too convenient to have been a coincidence, and implies that it was all Sky's doing: "Masterson, I had you in my big-time book. Now I suppose I'll have to reclassify you - under shills and decoys". His suspicions are passed on to Sarah who dumps Sky there and then, refusing to accept his denials.

In the meantime Sky has to make good his arrangement with Sarah to provide sinners to the Mission. Sarah would rather forget the whole thing, but Uncle Arvide Abernathy (Regis Toomey), who acts as a father-figure to her, warns Sky that "If you don't make that marker good, I'm going to buzz it all over town you're a welsher."

Feeling that he has little to lose anyway, Sky lies to Nathan about succeeding in the original bet and pays him the $1000. Nathan has continued the game in a sewer. Big Jule has lost a fortune but, with his revolver at his side, he won't let the game break up until he has recovered all his losses, which seems unlikely since "Big Jule cannot make a pass to save his soul". Sky overhears this and makes a bold bet: he will play and if he loses he will give all the other gamblers $1000 each; if he wins they are all to attend a prayer meeting at the Mission.

The Mission is near to closing when suddenly the gamblers come parading in, taking up most of the room. Sky won the roll. They grudgingly confess their sins, though they show little sign of repentance: "Well ... I was always a bad guy. I was even a bad gambler. I would like to be a good guy and a good gambler. I thank you." Even Big Jule declares: "I used to be bad when I was a kid. But ever since then I've gone straight, as I can prove by my record - 33 arrests and no convictions."

When Nathan tells Sarah that Sky denied winning the Cuba bet (which she knows he won), she hurries off in order to make up with him.

One who does repent is Nicely-Nicely Johnson (Stubby Kaye) who actually joins the Save-a-Soul Mission and appears to become close to General Cartwright (Kathryn Givney).

There is then a street double wedding, with Sky marrying Sarah, and Nathan marrying Adelaide (who is given away by Lieutenant Brannigan). They arrive in a food delivery van and leave in police cars, though this just seems to be an attempt at humor since Brannigan has been unable to find any witnesses against Sky and Nathan and their activities.