Guys and Dolls
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50 free Guys and Dolls trivia questions with answers — music quiz, new questions added Oct 2026.
Guys and Dolls has been called a perfect musical comedy, and it is easy to hear why. High-rolling gamblers, a strait-laced missionary and a nightclub singer with a very long engagement collide on Broadway, and almost every song became a standard. The show has been revived again and again on both sides of the Atlantic, and the starry 1955 movie carried it to an even bigger audience. This quiz covers the story and its wagers, the characters and the songs, from Adelaide's Lament to the big numbers for the crapshooters. It also goes backstage: who wrote the show, who first played the leads, which famous names turned up in later revivals, and how two of Hollywood's biggest stars came to share the screen without much liking each other. The questions start with easy openers for anyone who has seen the show or the movie once, then build to deep cuts for cast-album collectors. Every answer comes with a short explanation, so you learn something even when you guess.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In Guys and Dolls, Nathan Detroit bets that Sky Masterson cannot take Sarah Brown to dinner in which city?
Havana
Havana is where the strait-laced missionary lets her guard down, and a nightclub brawl sends the pair running. Nathan picked her because he was sure she would never go.
Q 02Which actor did his own singing as Sky Masterson in the 1955 film Guys and Dolls?
Marlon Brando
Marlon Brando sang every note himself, with no professional brought in to dub him. The producer wanted him because he was the world's biggest ticket-seller at the time.
Q 03Which singer played Nathan Detroit in the 1955 film Guys and Dolls after hoping to land the role of Sky?
Frank Sinatra
Frank Sinatra coveted the romantic lead and resented losing it, which soured the mood on set. A new song was written for his character to give him more to sing.
Q 04In the Guys and Dolls song Adelaide's Lament, which ailment does Adelaide blame on her endless engagement?
A cold
A cold that never clears is, her medical book suggests, her body's protest at a fiancé who keeps putting off the wedding. The number is often called a perfect comic song.
Q 05Guys and Dolls is based on short stories about New York gamblers and hustlers by which writer?
Damon Runyon
Damon Runyon wrote his Broadway tales in the 1920s and 1930s in a comic dialect all his own. He also spent decades as a newspaper sports reporter.
Q 06Which Guys and Dolls song does Sky Masterson sing before a make-or-break roll of the dice among the gamblers?
Luck Be a Lady
Luck Be a Lady later became a signature tune for a star of the film who never sang it on screen. The American Film Institute ranked the movie version among its 100 greatest film songs.
Q 07The 46th Street Theatre, where Guys and Dolls premiered in 1950, later became the Broadway home of which hit musical?
Hamilton
Hamilton opened there in 2015, long after the building was renamed the Richard Rodgers Theatre. The house has hosted eleven Tony-winning productions.
Q 08Which screen star phoned the director to ask for the part of Adelaide in the 1955 film Guys and Dolls?
Marilyn Monroe
Marilyn Monroe wanted the role, but her call did not sway the director. He insisted on the actress who had created the part on Broadway.
Q 09In 1955 three original Broadway leads took a shortened Guys and Dolls to which city for six months?
Las Vegas
Las Vegas saw the show twice a day at the Royal Nevada, the first time a Broadway musical was performed on the Strip.
Q 10Which TV series featured Sit Down, You're Rockin' the Boat from Guys and Dolls in its pilot episode?
Glee
Glee used the gospel-style number in its very first episode and brought it back for the season 3 finale. On stage a gambler sings it while describing a dream he invents on the spot.
Q 11Which songwriter wrote both the music and the lyrics for the 1950 Broadway musical Guys and Dolls?
Frank Loesser
Frank Loesser had spent most of his career writing lyrics for movie musicals before this score. He also won an Oscar for a wintry duet he first sang at parties with his wife.
Q 12What rank does Sarah Brown hold in the mission band that marches through Broadway in Guys and Dolls?
Sergeant
Sergeant Sarah Brown leads the band's call for Broadway's gamblers to repent. Her branch faces closure unless it can fill the seats at a revival gathering.
Q 13What does Sky Masterson offer to deliver to Sarah Brown's mission in return for a dinner date in Guys and Dolls?
A dozen sinners
Q 21Which film star played Sky Masterson in the 2005 West End revival of Guys and Dolls at the Piccadilly Theatre?
Ewan McGregor
Ewan McGregor led the cast for director Michael Grandage, opposite Jane Krakowski as Adelaide. The production ran for almost two years.
Q 22Which Hollywood star took over as Nathan Detroit during the West End run of Guys and Dolls that opened in 2005?
Patrick Swayze
Patrick Swayze was one of five replacements in the part, a list that also included Don Johnson and Neil Morrissey. The revival added a song first written for the 1955 film.
Q 23Which comic actor starred in the 1992 Broadway revival of Guys and Dolls as a marriage-shy gambler?
Nathan Lane
A dozen sinners, all genuine, is the offer, and Sarah later pledges the same number to her General. Sky then has to gamble against his fellow crapshooters to make good on it.
Q 14How long have Nathan Detroit and Miss Adelaide been engaged when the story of Guys and Dolls begins?
14 years
14 years of waiting is the running joke of the show, and it ends only in the final scene. By then the bridegroom has shut down his dice game at her insistence.
Q 15How does Sarah Brown react when Sky Masterson first kisses her at the mission in Guys and Dolls?
She slaps him
She slaps him, moments after the two have argued in song about the kind of person each expects to fall for. Their next kiss comes later, and that one is her idea.
Q 16Which spirit is hidden in the 'milkshake' Sky Masterson buys Sarah Brown on their dinner date in Guys and Dolls?
Rum
Rum, specifically Bacardi, is what gives the drink its kick. A tipsy Sarah ends the evening fleeing a nightclub brawl and then kissing the gambler.
Q 17Which Guys and Dolls song does a tipsy Sarah Brown sing to Sky Masterson after their eventful dinner date?
If I Were a Bell
If I Were a Bell became a jazz standard after trumpeter Miles Davis recorded it with a quintet that included John Coltrane. On stage it marks the moment the missionary lets go.
Q 18Where does Nathan Detroit move his floating crap game in the second act of Guys and Dolls to hide from the police?
A sewer
A sewer keeps the game out of sight of the police lieutenant who has been hounding it all along. The dice have been rolling for twenty-four hours when Sky arrives.
Q 19What must the gamblers do if Sky Masterson wins his thousand-dollar-a-head dice roll in Guys and Dolls?
Attend a prayer meeting
They must attend a prayer meeting at the mission, while a loss would have cost Sky a thousand dollars for every man present. An offhand remark about a soul gave him the idea.
Q 20What is the name of the nightclub where Miss Adelaide headlines with her chorus of dancers in Guys and Dolls?
The Hot Box
The Hot Box is where Adelaide and her chorus perform a nightclub number in each act. After the first, she asks Nathan yet again to set a date.
Nathan Lane had taken his stage first name from the very character he played in that revival. Another actor called Joseph Lane was already registered with the actors' union.
Q 24Which film comedy star took over as Miss Adelaide in London's West End production of Guys and Dolls in June 2016?
Rebel Wilson
Rebel Wilson joined the show after it had moved from the Savoy to the Phoenix Theatre. The staging had begun life two summers earlier in Chichester.
Q 25The author whose stories inspired Guys and Dolls was born in a Kansas town sharing its name with which New York borough?
Manhattan
Manhattan, Kansas, was where his father edited the town newspaper. The writer moved to New York City in 1910 and made Broadway's gamblers his subject.
Q 26The short stories behind Guys and Dolls use a comic dialect mixing slang with formal speech that lacks which feature?
Contractions
Contractions are avoided throughout the stories, so small-time hustlers say every word in full while still talking in street slang. The show's writers kept that comic flavor for the stage.
Q 27What do the gamblers in Guys and Dolls tell Lt. Brannigan their gathering is, forcing Nathan Detroit to play along?
A bachelor party
A bachelor party for Nathan is the alibi, which leaves him little choice but to agree to elope with Adelaide. The men were really waiting for his dice game to start.
Q 28What has Miss Adelaide been claiming for twelve years in letters to her mother in Guys and Dolls?
That she is married
That she is married, with five children, is the story her mother has been reading all this time. Adelaide admits the invention to Nathan while pressing him to make it true.
Q 29Where does the 1955 film Guys and Dolls stage its closing double wedding, with Nicely-Nicely on bass drum?
Times Square
Times Square hosts both couples at once in the film, with Sky and Sarah beside Nathan and Adelaide. On stage, only one of the two ceremonies is shown.
Q 30Which dancing star was an early pick for Sky in the film Guys and Dolls until his studio refused to loan him?
Gene Kelly
Gene Kelly was under contract to MGM, which would not release him to a rival producer. In an ironic twist, MGM ended up distributing the finished film anyway.