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.

Sergeant Sarah Brown: You want to take me to dinner in *Havana, Cuba?*
Sky Masterson: Well, they eat in Cuba the same as we do.
Arvide Abernathy: And I never saw until now how much in love with him you are.
Sergeant Sarah Brown: I'll get over it.
Arvide Abernathy: Why would anyone want to get over the one thing you hope for from the minute you're born and remember until the day you die?
Sergeant Sarah Brown: I'll get over it.
Arvide Abernathy: Why? Because it's the greatest reward that woman or man can have on this earth? To love and to be loved?
Sky Masterson: One of these days in your travels, a guy is going to show you a brand-new deck of cards on which the seal is not yet broken. Then this guy is going to offer to bet you that he can make the jack of spades jump out of this brand-new deck of cards and squirt cider in your ear. But, son, do not accept this bet, because as sure as you stand there, you're going to wind up with an ear full of cider.
Sergeant Sarah Brown: That bacardi flavor, it certainly makes a difference, doesn't it?
Sky Masterson: Oh, yeah. Nine times out of ten.
Sergeant Sarah Brown: You know, this would be a wonderful way to get children to drink milk!
Sky Masterson: [reading a verse of the day card] "There is no peace unto the wicked. Proverbs" This is wrong
Sergeant Sarah Brown: Let's just say it's a matter of opinion, shall we?
Sky Masterson: I made a statement of fact. This is wrong.
Sergeant Sarah Brown: How dare you! Even if this is not a church, it is a mission! How dare you blaspheme!
Sky Masterson: How dare you misquote the Bible!
Miss Adelaide: And what was that about?
Nathan Detroit: His wife's having a baby.
Miss Adelaide: But why is he asking you?
Nathan Detroit: He's nervous, it's his first wife.
Nathan Detroit: I have been running the crap game since I was a juvenile delinquent.
Miss Adelaide: Speaking of chronic conditions, happy anniversary.
Nathan Detroit: Southstreet, give your testimony.
Benny Southstreet: I plead the fifth commandment.
Sky Masterson: [after Sarah orders milk in a Havana nightclub] Now, don't make a spectacle of yourself... You are a United States citizen in a foreign country, have you no pride in what the rest of the world thinks about Americans?
Nathan Detroit: If a guy did not have a doll, who would holler on him?
Harry the Horse: I just acquired five thousand fish.
Nicely Nicely Johnson: Five thousand? If it can be told, where did you take on this fine bundle of lettuce?
Harry the Horse: I have nothing to hide. I collected the reward on my father.
Benny Southstreet: It is an advantage to have a successful father. Nobody ever wanted my old man for as much as five hundred.
Sky Masterson: [after Sarah slaps him] Well, that makes it necessary for me to stop in again. Matthew 5:39. Don't bother looking it up, it's the bit about the other cheek.
Sky Masterson: Daddy, I got cider in my ear
Sky Masterson: I am not putting the knock on dolls. It's just that they are something to have around only when they come in handy... like cough drops.
Sergeant Sarah Brown: Apparently you're a successful gambler.
Sky Masterson: Is it wrong to gamble, or only to lose? I'd better come back for help when I'm broke.
Sergeant Sarah Brown: Please don't misunderstand. It's just so unusual for a successful sinner to be unhappy about sin.
Sky Masterson: Besides, my unhappiness came up very suddenly. Maybe it'll go away again.
Arvide Abernathy: We can keep you unhappy, son. Give us a chance.
Nicely Nicely Johnson: Nicely, nicely.
Sky Masterson: I didn't ask how you are.
Nicely Nicely Johnson: Don't.
Benny Southstreet: [about the cab that Nathan told him to take Adelaide to the Hot Box in] But who's going to pay for it?
Miss Adelaide: I am, of course!
Miss Adelaide: Nathan, no matter how terrible a fellow seems, you can never be sure that some girl won't go for him. Take us.
Sky Masterson: For two weeks I gambled in green pastures. The dice were my cousins and the dolls were agreeable with nice teeth and no last names.
Sky Masterson: Figuring weight for age, all dolls are the same.
Sky Masterson: [after observing that Sarah's mission is doing poorly] Do I give you a fair rundown?
Sergeant Sarah Brown: I wouldn't know. I've never had a rundown.
Big Jule: If it gets around in Chicago that I went to a prayer meeting, no decent person will talk to me!
Harry the Horse: But Big Jule cannot win if he plays with honest dice!
Sky Masterson: General, on behalf of the former sinners of the future I would like to protest the closing of this mission.
Sky Masterson: It is my understanding that the Constitution of the United States allows everybody the free choice between cheesecake and strudel.
Sky Masterson: You know, I imagine there's only one thing that's been in as many different hotel rooms as I have: the Gideon Bible. Don't tangle with me on the Good Book. I must've read it through at least a dozen times.
Sergeant Sarah Brown: If all that was no help to you...
Sky Masterson: Look, the bells rang, they really rang. They weren't magical bells for lovers full of rum and music on a make-believe island; They rang to tell us what time it is.
Nathan Detroit: Everybody in the whole world who hates me is now here.
Nathan Detroit: [singing] What's playing at the Roxy? I'll tell you what's playing at the Roxy. Picture about a Minnesota man so in love with a Mississippi girl that he sacrifices everything and moves all the ways to Biloxi. That's what's playing at the Roxy.
Benny Southstreet: [singing] What's in the daily news? I'll tell you what's in the daily news. Story about a guy who bought his wife a small ruby with what otherwise would have been his union dues. That's what's in the daily news.
Nicely Nicely Johnson: [singing] What's happening all over? I'll tell you what's happening all over. Guy sitting home by a television set who used to be something of a rover. That's what's happening all over.
Nathan Detroit, Benny Southstreet, Nicely Nicely Johnson: [singing] Love is the thing that has licked 'em!
Nathan Detroit: [singing] And it looks like I'm just another victim.
Harry the Horse: So, my sin is that when Sky was rolling us, I wished that I could've won the thousand bucks instead of having to come here. But, now that I'm here - I still wish it!
Nathan Detroit: [after declining a bet that he cannot say what color his tie is] Polka dots. In the whole world, only Nathan Detroit could blow a thousand bucks on polka dots.
Nathan Detroit: [to Nicely and Benny] Take Adelaide to the Hot Box. In a cab.
Miss Adelaide: But it's only a couple of blocks.
Nathan Detroit: The streets are covered with tourists and I do not want you molested.
Big Jule: Tell me, how long have you known the doll?
Nathan Detroit: 14 years.
Big Jule: Let's shoot crap!
Big Jule: Well, I used to be bad when I was a kid, but ever since then I've gone straight, as has been proved by my record: Thirty-three arrests and no convictions!
Sky Masterson: The companionship of a doll is a pleasant thing even for a period of time running into months. But for a close relationship that can last us through all the years of our life, no doll can take the place of aces back to back.
Sky Masterson: All right. We'll lay it on the line. From now on we'll deal the hand open.
Sergeant Sarah Brown: Could you say that in English?
Lieutenant Brannigan: [to Big Jule at Mindy's] Where are you from, sir?
Big Jule: East Cicero, Illinois!
Lieutenant Brannigan: And what is your occupation?
Big Jule: I'm a scoutmaster!
Lieutenant Brannigan: Don't ever help my mother across the street!
Nathan Detroit: Still, you will admit that Mindy's cheesecake is the greatest alive.
Sky Masterson: Gladly. Furthermore, I am quite partial to Mindy's cheesecake.
Sky Masterson: You remember that tune pretty well.
Sergeant Sarah Brown: It keeps running through my heart.
Sky Masterson: It has words, you know.
Sergeant Sarah Brown: Something about "amor, amor" I'll bet.
Sky Masterson: It's about you. It's about you right now...
[singing]
Sky Masterson: Your eyes are the eyes of a woman in love...
Lieutenant Brannigan: What brings all these senior delinquents together?
Nathan Detroit: They got lonely. How am I supposed to know?
Lieutenant Brannigan: And why are they all wearing red carnations?
Nathan Detroit: They are also all wearing pants.
Nathan Detroit: Would you not agree that Mindy's cheesecake is the best cheesecake alive?
Sky Masterson: We have time to catch the last plane back to New York.
Sergeant Sarah Brown: People miss planes. It happens.
Sky Masterson: Yeah? It also happens that people win with loaded dice.
Sergeant Sarah Brown: I know what I'm doing.
Sky Masterson: Do you, kid?
[kisses her nose]
Sky Masterson: I don't.
Benny Southstreet: I've always been a bad guy, and a bad gambler. From now on, I would like to be a good guy, and a good gambler. I thank you.
Sergeant Sarah Brown: [after Sky confesses that their date is just part of a bet] Why not? You're a gambler. And darling... you are also a chump.