Prohibition Trivia
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50 free Prohibition trivia questions with answers — history quiz, new questions added Aug 2026.
46 free Prohibition trivia questions with answers. From January 1920 to December 1933 the United States tried to stop drinking, and mostly failed in ways that make for great trivia. This Prohibition quiz covers how the law happened (the Anti-Saloon League, Wayne Wheeler, Carrie Nation and her hatchet, the veto Congress overrode), how people got around it (medicinal whiskey, sacramental wine, grape bricks with helpful warnings, Detroit's river trade, the schooner captain who never watered his rum) and how it ended (3.2 beer, Pauline Sabin's repeal army and the only amendment ever ratified by state conventions). The gangsters are here too: Capone's tax conviction, the Saint Valentine's Day Massacre, George Remus shooting his wife on the way to their divorce, and the Untouchables. So are the strange consequences: poisoned industrial alcohol, jake leg, moonshine cars that became NASCAR and the state that stayed dry until 1966. The early questions suit anyone who has seen The Untouchables or Boardwalk Empire; the later ones are for history buffs. Every answer was checked against a reference page and shows its source once you have answered.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Under federal law, what stayed legal throughout Prohibition?
Drinking liquor
Drinking liquor was never a federal crime: the ban covered making, selling and transporting alcohol, so many people stockpiled wine and spirits in 1919 before sales stopped.
Q 02Which amendment to the US Constitution established Prohibition?
Eighteenth
Eighteenth, and the only amendment ever repealed: the Twenty-first struck it out in December 1933, less than fourteen years after the country went dry.
Q 03Which salad was first tossed in 1924 at a Tijuana restaurant that drew Americans dodging Prohibition?
Caesar salad
Caesar salad comes from Caesar's, the Tijuana restaurant that Italian-born Caesar Cardini ran just across the border so that he could serve alcohol to visiting Americans.
Q 04Which president's veto of the Volstead Act did Congress override in October 1919?
Woodrow Wilson
Woodrow Wilson's veto lasted barely a day: Congress had overridden it by 28 October 1919, and Prohibition began on schedule the following January.
Q 05Which pressure group, led by lobbyist Wayne Wheeler, did the most to push Prohibition through?
The Anti-Saloon League
The Anti-Saloon League cared about a single issue: under Wheeler it turned alcohol into a wedge in elections and got one dry candidate after another into office.
Q 06Which temperance activist, arrested some 30 times, smashed saloons with a hatchet?
Carrie Nation
Carrie Nation called her raids 'hatchetations' and paid her fines from lecture fees and the sale of souvenir hatchets.
Q 07Maine banned liquor by ordinary law, but in 1881 which state first wrote a ban into its constitution?
Kansas
Kansas voters approved the amendment in 1880, it took effect in 1881, and the state kept its ban until 1948, fifteen years after national Prohibition ended.
Q 08Frances Willard led which temperance organisation?
Woman's Christian Temperance Union
The Woman's Christian Temperance Union changed course under Willard, who in 1879 replaced a president set on alcohol alone and tied the dry cause to winning votes for women.
Q 09Senator Sheppard said repealing Prohibition was as likely as a humming-bird flying to which planet?
Mars
Mars was the boast of Morris Sheppard, the Texas senator called 'the father of national Prohibition' for introducing the dry amendment, which was repealed within fourteen years of taking effect.
Q 10What were Prohibition's illegal bars called, tens of thousands of which operated in New York City alone?
Speakeasies
Speakeasies got their name from the need to speak quietly about them so the police would not hear; the same illicit bars were also known as 'blind pigs'.
Q 11Which spirit could Americans still buy legally at a drugstore during Prohibition if a doctor prescribed it?
Whiskey
Whiskey was the standard 'medicine': doctors wrote an estimated 11 million liquor prescriptions a year in the 1920s, and one was cited for writing 475 in a single day.
Q 12Which drugstore chain's boom from about 20 stores in 1919 to hundreds by 1930 is often put down to medicinal alcohol sales?
Walgreens
Walgreens tells it differently: founder Charles Walgreen credited the growth to the malted milkshake his soda fountains introduced in 1922.
Q 13Grape 'wine bricks' sold during Prohibition carried a label warning buyers not to do what?
Leave the jug in a cupboard
Q 21Which motor sport openly traces its origins to Prohibition-era bootleg drivers racing for pride?
NASCAR
NASCAR's roots lie with drivers who tuned ordinary-looking cars to outrun federal agents on back roads and then raced each other at weekends; Bill France organised the sport in the late 1940s.
Q 22Al Capone was finally sentenced to federal prison in 1931 for what crime?
Tax evasion
Tax evasion was the charge that stuck: prosecutors showed Capone had paid no tax on his illegal income, and he was sentenced to 11 years, part of it served on Alcatraz.
Q 23The seven men shot in the 1929 Saint Valentine's Day Massacre belonged to which gang boss's organisation?
Bugs Moran
Leave the jug in a cupboard for about three weeks, the label warned, and the juice would turn into wine: the 'warning' was really the recipe.
Q 14During Prohibition, federal officials ordered poison added to what, a policy blamed for thousands of deaths?
Industrial alcohol
Industrial alcohol was being stolen and redistilled by bootleggers, so officials made it deadlier; New York's medical examiner Charles Norris said the government bore 'the moral responsibility' for the deaths.
Q 15'Canned heat', jellied alcohol that desperate Prohibition drinkers strained and drank, was sold under what brand name?
Sterno
Sterno drinking left its mark on the blues: Tommy Johnson's 1928 'Canned Heat Blues' laments the habit, and the 1960s band Canned Heat took its name from the song.
Q 16'Jake leg', a paralysis that struck tens of thousands in 1930, came from an adulterated patent medicine made from what?
Jamaica ginger
Jamaica ginger extract, or 'jake', was mostly alcohol and legal to sell; bootleggers added a plasticiser to slip it past government tests, and the additive turned out to attack the nerves.
Q 17An estimated three-quarters of the liquor smuggled into Prohibition America crossed from Canada by way of which city?
Detroit
Detroit lay just across the river from Windsor, Ontario: in winter smugglers simply drove over the ice, and by 1929 liquor smuggling was the city's second-biggest trade.
Q 18Rum-runner Bill McCoy's reputation for what practice is popularly, but wrongly, said to have given us 'the real McCoy'?
Never watering his liquor
Never watering his liquor did make McCoy's cargo a byword for the genuine article, but the phrase was already in print by 1881, when he was a small child.
Q 19Which Canadian founded the Distillers Corporation in 1924, then bought Seagram and profited from Prohibition?
Samuel Bronfman
Samuel Bronfman also planned for the day the ban ended: when repeal came, Seagram had huge stocks of aged spirits ready for the reopened American market.
Q 20Home-distilled liquor was 'bathtub gin' in northern cities, but what was it called in the rural South?
Moonshine
Moonshine, a word for illicit liquor since the 1780s, points to work done under cover of night, the hour when Prohibition-era stills were fired to avoid discovery.
Bugs Moran was not in the garage when gunmen dressed as policemen lined seven of his men against a wall; the killings were widely blamed on his rival Al Capone.
Q 24What nickname did Eliot Ness's small team of Chicago Prohibition agents earn?
The Untouchables
The Untouchables got the name from the press after Ness's agents turned down bribes from Capone's organisation.
Q 25Who won the Best Supporting Actor Oscar for De Palma's 1987 film about Eliot Ness and Al Capone?
Sean Connery
Sean Connery won the Oscar as an Irish-American cop, yet a 2003 Empire magazine poll named the performance the worst film accent of all, his Scottish burr intact.
Q 26New York agents Izzy Einstein and Moe Smith became famous for using what tactic to raid illegal bars?
Disguises
Disguises and put-on foreign accents got the pair through doors that stayed shut to other agents, and between them they made thousands of arrests.
Q 27"King of the Bootleggers" George Remus was acquitted in 1927 after shooting whom in a public park?
His wife
His wife, Imogene, had begun an affair with a federal investigator while Remus was in prison, and the pair set about stripping his fortune.
Q 28Chicago lawyer George Remus, the 'King of the Bootleggers', moved to which city to be close to America's stores of bonded liquor?
Cincinnati
Cincinnati put Remus within reach of the distilleries he bought up, along with pharmacies, under cover of making and selling medicinal liquor: a loophole that made him a fortune.
Q 29Which justice wrote the 'right to be let alone' dissent in the 1928 wiretapping case of bootlegger Roy Olmstead?
Louis Brandeis
Louis Brandeis lost by five votes to four, but his dissent won in the end: in 1967 the Supreme Court abandoned the Olmstead rule and treated wiretapping as a search.
Q 30Which bootlegger took over boxer Jack Johnson's Harlem nightclub in the early 1920s and renamed it the Cotton Club?
Owney Madden
Owney Madden limited the audience to white patrons even as Black stars such as Duke Ellington and Cab Calloway made their names on its stage.