This about the film. For the stage musical, see Guys and Dolls (musical).
- Marlon Brando - Sky Masterson
- Frank Sinatra - Nathan Detroit
- Jean Simmons - Sarah Brown
- Vivian Blaine - Adelaide
- Stubby Kaye - Nicely Nicely Johnson
- Johnny Silver - Benny Southstreet
- Danny Dayton - Rusty Charlie
- Robert Keith - Lieutenant Brannigan
- B.S. Pully - Big Jule
- Sheldon Leonard - Harry the Horse
- Regis Toomey - Arvide Abernethy
- Kathryn Givney - General Cartwright
Gambler Nathan Detroit is under pressure from all sides. He has to organize an unlicensed crap game but the police, led by Lieutenant Brannigan, 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. Adding to Nathan's problems, his fiancée, Miss Adelaide, 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, 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, a straight-walking sister at 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 pretends that he is a gambler who wants to change. Sarah sees how expensively dressed he is and she is suspicious.
Seeing that the Mission is and has been empty and unsuccessful, "a store full of repentance and no customers", Sky suggests a bargain. He will get a dozen sinners into the Mission for her Thursday night meeting in return for her having dinner with him in Havana. With General Matilda Cartwright threatening to close the Broadway branch for lack of participation, Sarah has little choice left, and agrees to the date.
Meanwhile, confident that he will win his bet with Sky, Nathan has gathered together all the gamblers, including a visitor that tough-guy Harry the Horse has invited: Big Jule, a Chicago mobster. When Lieutenant Brannigan appears and notices this gathering of "senior delinquents", all gathered at Mindys, Nathan's sidekick, Benny Southstreet, covers it up 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 notices the Save a Soul Mission band passing by and sees that Sarah is not among them, he collapses on the realization that he has lost his bet with Sky. He has no money and nowhere to house the crap game, and, since Adelaide was present at the "wedding announcement" Benny Southstreet dreamed up, he is now apparently committed to actually marrying Adelaide. He does love Adelaide, but is 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, partly through disguised alcoholic drinks, and they begin to fall in love with one another. He even confesses that the whole date 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 crap 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. Sarah is equally suspicious that Sky has had something to do with organizing the crap game at the Mission and she angrily takes her leave of him, refusing to accept his denials.But Sky still 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, who acts as a kind of father figure to her, warns Sky that he will ruin his reputation if Sky welches.
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 and 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 $1000. Nathan tells Big Jule he now has money to play him again, but Harry the Horse says that Big Jule can't play without cheating because "he cannot make a pass to save his soul". Sky overhears this, and the phrasing inspires him to make a bold bet: He will roll the dice, 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. 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." 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 in order to make up with him.
It all ends with a double wedding in the middle of Times Square, with Sky marrying Sarah, and Nathan marrying Adelaide, who is given away by Lieutenant Brannigan. Arvide Abernathy performs the dual ceremony. Nicely-Nicely has joined the Save a Soul Mission, and he and Sarah's assistant are sweet on each other. As the film closes, the two newlywed couples are escorted from the wedding to their respective love nests inside police cars, with lights festively flashing and sirens blaring.
- "Fugue for Tinhorns" – Nicely, Benny, Rusty
- "Follow the Fold" – Sarah, Mission Band
- "The Oldest Established" – Nathan, Nicely, Benny, Guys
- "I'll Know" – Sarah, Sky
- "Pet Me Poppa" – Miss Adelaide, Hot Box Girls
- "Adelaide's Lament" – Miss Adelaide
- "Guys and Dolls" – Nicely, Benny
- "Adelaide" - Nathan and Gamblers
- "If I Were a Bell" – Sarah
- "A Woman In Love" – Sky, Sarah
- "Take Back Your Mink" – Miss Adelaide, Hot Box Girls
- "Luck Be a Lady" – Sky, Guys
- "Sue Me" – Miss Adelaide, Nathan
- "Sit Down, You're Rockin' the Boat" – Nicely, Gamblers and Missionaries
- "Guys and Dolls (Reprise)" – Company