Gangsters
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50 free Gangsters trivia questions with answers — history quiz, new questions added Oct 2026.
Gangsters have fascinated the public since the 1920s, when Prohibition turned neighbourhood toughs into millionaires and the newspapers gave every one of them a nickname. The real stories are stranger than the films: bosses who courted the press, bank robbers who became folk heroes, and lawmen who built careers on catching them. This quiz covers old-school gangsters and outlaws from the early 1900s onward: Al Capone's Chicago, John Dillinger and the Depression bank robbers, Bonnie and Clyde, Lucky Luciano and the New York Mafia, plus a few mobsters from later decades and from overseas. Expect questions on famous nicknames, shootouts, prison stories, underworld slang and the cases that ended each career. It suits history buffs, true crime fans and anyone hosting a trivia night. If you came looking for a gangster name of your own, the nicknames in these questions are a good place to start, because every one was earned by a real person. Each answer comes with a short explanation.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Al Capone ran Chicago's bootlegging empire for years, but which crime finally sent him to federal prison?
Tax evasion
Tax evasion earned Al Capone an 11-year sentence and a $50,000 fine in October 1931. Prosecutors had learned to prove a gangster's hidden income from his luxurious lifestyle.
Q 02Killers posing as a police raid shot seven men of Bugs Moran's gang in a Chicago garage on which holiday?
Valentine's Day
Valentine's Day 1929 became a byword for gangland killing, yet nobody was ever convicted of the murders. The likely target, Bugs Moran, was running late and never reached the garage.
Q 03Federal agents shot bank robber John Dillinger dead as he walked out of which kind of Chicago building?
A movie theater
A movie theater called the Biograph was showing the Clark Gable crime drama Manhattan Melodrama that night. John Dillinger tried to flee when agents closed in and was fatally shot.
Q 04Which newly opened federal prison took in Al Capone in 1934 and let him play banjo in the inmate band?
Alcatraz
Alcatraz received Al Capone in August 1934, and good behaviour won him a place in its band, the Rock Islanders. The group gave regular Sunday concerts for the other inmates.
Q 05Which Las Vegas casino did mobster Bugsy Siegel take over and open in 1946, months before he was shot dead?
The Flamingo
The Flamingo opened on December 26, 1946, struggled without a finished hotel and shut for weeks. A sniper killed Bugsy Siegel through a window in Beverly Hills the following June.
Q 06Which weapon, developed by a US Army general, became known in Prohibition gangland as the Chicago typewriter?
Tommy gun
The Tommy gun, formally the Thompson submachine gun, was the work of Brigadier General John T. Thompson. Its use by Prohibition criminals made it famous, and the press shortened his name.
Q 07Thirty million viewers watched Geraldo Rivera open Al Capone's secret vault live on television, revealing what?
Dirt and empty bottles
Dirt and empty bottles were all the walled-off room under Chicago's Lexington Hotel held in 1986. Geraldo Rivera admitted defeat on air and apologised to the audience.
Q 08A posse led by a retired Texas Ranger ambushed and killed Bonnie and Clyde on a rural road in which state?
Louisiana
Louisiana officers joined four Texas lawmen in the trap on Highway 154 in Bienville Parish on May 23, 1934. The bullet-riddled car later became a popular travelling attraction.
Q 09New York gambler Arnold Rothstein, nicknamed The Brain, was widely accused of fixing which sporting event in 1919?
The World Series
The World Series of 1919 was thrown by Chicago White Sox players allegedly paid by Arnold Rothstein's agents. The Great Gatsby nods to the scandal through its gambler Wolfsheim.
Q 10Which Prohibition agent led the Chicago squad that a newspaper nicknamed the Untouchables for refusing mob bribes?
Eliot Ness
Eliot Ness combed the records of every Prohibition agent to build a team of about ten he could trust. He later spent years in Cleveland as the city's safety director.
Q 11Close friends called Al Capone Snorky, slang for a sharp dresser, but which nickname did the gangster loathe?
Scarface
Scarface came from three knife slashes dealt by the brother of a woman Al Capone had insulted while working the door of a bar.
Q 12In which place was Al Capone born to immigrant parents who came from a small town near Naples?
Brooklyn
Brooklyn was where Al Capone was born on January 17, 1899, and where he grew up. He only moved to Chicago, the city that made him notorious, in his early twenties.
Q 13Lucky Luciano won early release in 1946 for wartime help to the US Navy, provided he left for which country?
Italy
Italy took Lucky Luciano back after his organization promised the Navy intelligence from New York's waterfront. He died there in 1962, and his body was returned to the US for burial.
Q 21Which bank robber, born Lester Gillis, killed three FBI agents before dying after a 1934 gun battle near Chicago?
Baby Face Nelson
Baby Face Nelson owed the name to being a short man with a youthful appearance, though fellow criminals called him Jimmy. He killed more FBI agents than any other criminal.
Q 22Which woman did J. Edgar Hoover call the decade's most dangerous criminal brain after FBI agents shot her in 1935?
Ma Barker
Ma Barker died beside her son Fred after an hours-long shootout in Florida. Those who knew her insisted she had no criminal role and that the label was invented to justify the shooting.
Q 23Which charity did Al Capone sponsor in a Chicago storefront during the Depression in an effort to polish his image?
Q 14Bonnie and Clyde were killed with Clyde Barrow at the wheel of a V8 car built by which company?
Ford
Ford built the V8 that the posse riddled with bullets as it slowed on the road. A casino near Las Vegas bought the car in 1988 for about $250,000.
Q 15Which constitutional change banned alcohol from 1920 and handed gangsters like Al Capone a booming bootleg trade?
The 18th
The 18th Amendment took effect in January 1920 and is the only one ever repealed, in 1933. Al Capone was estimated to earn $60 million a year from illegal liquor while it lasted.
Q 16Twins Ronnie and Reggie Kray became celebrity nightclub owners while running organised crime in which 1960s city?
London
London society embraced the Kray twins, who were photographed by David Bailey and interviewed on television. Both were sentenced to life imprisonment in 1969.
Q 17Which Teamsters union leader with alleged mob ties vanished in 1975 and was declared legally dead seven years later?
Jimmy Hoffa
Jimmy Hoffa led the Teamsters from 1957 to 1971 and is thought to have been murdered in a Mafia hit. An autobiography he had been working on came out a few months after he disappeared.
Q 18Which Mafia code of silence forbids members from cooperating with the authorities, on pain of death?
Omertà
Omertà goes beyond refusing to answer the authorities: it also demands turning a blind eye to the illegal activities of other people.
Q 19Which Mafia rank, popularised in English by the novel The Godfather, belongs to the boss's trusted adviser?
Consigliere
Consigliere is also an everyday title for city council members in Switzerland. In a crime family, the holder advises the boss and sometimes serves as the right-hand man.
Q 20Which New York crime boss was dubbed the Teflon Don after three high-profile trials ended without a conviction?
John Gotti
John Gotti was finally convicted in 1992 after his underboss, Sammy "the Bull" Gravano, agreed to testify against him. The earlier acquittals were later found to be tainted by jury tampering.
A soup kitchen
A soup kitchen at 935 South State Street served breakfast, lunch and dinner to an average of 2,200 Chicagoans a day. On Thanksgiving in 1930 it fed 5,000.
Q 24Which untreated disease eroded Al Capone's mind so badly that he spent a year of his sentence in a prison hospital?
Syphilis
Syphilis, most likely caught while he worked as a brothel bouncer in Chicago, was diagnosed in his brain in 1938. Al Capone ended his sentence confused and disoriented.
Q 25Which New York prison up the Hudson put mob boss Lepke Buchalter and the Rosenbergs to death in its electric chair?
Sing Sing
Sing Sing sent 614 men and women to the electric chair nicknamed Old Sparky before New York's death penalty ended. Lepke Buchalter went to it on March 4, 1944.
Q 26Anna Sage, the so-called Woman in Red, betrayed John Dillinger to federal agents in the hope of avoiding what?
Deportation
Deportation to her native Romania went ahead anyway, despite the bargain Anna Sage struck with the FBI. She was a brothel keeper whom officials classed as an undesirable alien.
Q 27John Dillinger claimed he bluffed his way out of a supposedly escape-proof Indiana jail by waving what at the guards?
A wooden gun
A wooden gun he said he had whittled was enough to cow the guards at Crown Point. Driving the sheriff's stolen car across a state line then made him a federal fugitive.
Q 28Which pastime did Bonnie Parker take up in a Texas jail and keep pursuing while on the run with Clyde Barrow?
Writing poetry
Writing poetry gave Bonnie Parker "The Trail's End", better known as "The Story of Bonnie and Clyde". A handwritten poem was among the belongings the gang abandoned when fleeing police in Joplin.
Q 29In popular legend, Machine Gun Kelly coined which nickname for FBI agents as he surrendered unarmed in Memphis?
G-Men
G-Men is short for government men. Machine Gun Kelly was arrested alongside his wife Kathryn, and both received life sentences for kidnapping an oil tycoon.
Q 30Which folk singer wrote a 1939 ballad that painted Oklahoma bank robber Pretty Boy Floyd as generous to the poor?
Woody Guthrie
Woody Guthrie drew on the tale that the robber destroyed mortgage papers during raids, a story never confirmed. Oklahoma locals called Pretty Boy Floyd the Robin Hood of the Cookson Hills.