On January 16, 1919 – Prohibition began in the United States. A daring experiment with sobriety, the sale of alcoholic beverages was forbidden by the 18th Amendment to the U.S Constitution. Over a 13 year period, the unpopular law sparked a nationwide increase in bootleggers and criminal enterprises. Although this time period resulted in a lot of bloodshed, it also has inspired some of the greatest films ever; so mix yourself some bathtub gin and enjoy our selection of nine great bootlegging movies.



Loosely based on Al Capone’s life, Howard Hughes’ SCARFACE focuses on Tony Camonte’s (Paul Muni) brutal rise to the top of Chicago’s bootlegging underworld. Camonte, originally a low level bodyguard, kills any speakeasy rivals that stand in his way from total control of the Chicago bootlegging racket. Camonte’s ruthless tactics payoff, as he not only becomes the king of Chicago’s criminal world, but also wins the woman of his desire. However, Camonte’s aggressive tactics catch the attention of Chicago’s police, ultimately resulting in his downfall.


Fun Fact: “X” marks the spot. Director Howard Hawks included an “X” motif in SCARFACE to signify a death in the film.


Michael Schultz’s GREASED LIGHTNING tells the story of the first African-American NASCAR Hall of Famer Wendell Scott (Richard Pryor). Scott, a post-World War II cab driver and thrill seeker, harnesses his driving skills by transporting prohibited moonshine throughout the state of Virginia. After Scott dominates the local talent, such as white race car drivers and police officers, his extraordinary driving abilities earn him a place on the race track. Soon after, Scott commits himself to becoming a champion race car driver.


Fun Fact: Maynard Jackson Jr., Atlanta’s first African-American mayor, appears in the film.


Brian De Palma’s THE UNTOUCHABLES highlights Elliot Ness’s (Kevin Costner) federal task force assigned to bring down the notorious Al Capone(Robert De Niro). As 1920s prohibition Chicago is clutched by mob boss Capone’s iron grip, Ness assembles a team of mismatched law enforcement agents to persecute Capone in any way possible. As Ness’s task force seeks to take down Capone’s criminal syndicate, Capone wages an all out war against Ness and all who associate with his task force. Sean Connery’s performance in THE UNTOUCHABLE earned him an Oscar and Golden Globe for best supporting actor.


Fun Fact: Robert De Niro was eager to portray Al Capone as accurate as possible, driving him to use Al Capone’s personal tailors to make him an exact replica of Capone’s suits.

LAWLESS (2012)

John Hillcoat’s LAWLESS centers around three Virginian brothers and their struggle to profit from Prohibition in the 1920s. As the Bondurant brothers (Shia LaBeouf, Tom Hardy, Jason Clarke) establish their own distillery and provide illegal moonshine throughout their Virginia county, they fight to remain profitable against other local bootleggers and the sadistic Special Deputy Charley Rakes (Guy Pearce). LAWLESS was screened during the 2012 Cannes Film Festival and was nominated for the Palme d’Or.


Fun Fact: The Russian translation for the title of LAWLESS is “The Drunkest Region in the World”.


Sergio Leone’s ONCE UPON A TIME IN AMERICA chronicles the life of former prohibition-era mobster David ‘Noodles’ Aaronson (Robert De Niro). After receiving a letter regarding a former gang member’s reburial, Noodles goes back to his old neighborhood to confront his previous crime partner Maximilian ‘Max’ Bercovicz (James Woods) and reminisce about the criminal life he left behind. ONCE UPON A TIME IN AMERICA is a multilayered epic tale that not only examines bootlegging in 1920s New York City, but also provides insight into companionship, betrayal, love, envy and loss.


Fun Fact: Although the length of the film is 229 minutes, Warner Brothers removed an additional 90 minutes from the feature. The additional 90 minutes has made some viewers theorize the entire film could have been merely a long opium-induced hallucination.


Billy Wilder’s SOME LIKE IT HOT follows the adventures of two struggling musicians who have to dress up as women in order to hide from the mob. When Joe (Tony Curtis) and Jerry (Jack Lemmon) witness the bloody St. Valentine’s Day massacre between rival bootleggers, they need to flee Chicago as soon as possible. Desperate to leave the city, the duo disguise themselves as female musicians and escape with an all-girl band. While in disguise Joe and Jerry find themselves infatuated with the lovely Sugar Kane Kowalczyk (Marilyn Monoroe). SOME LIKE IT HOT is a comedic masterpiece, earning the feature three Academy Awards, including Best Actor and Best Director.


Fun Fact: After Tony Curtis and Jack Lemmon put on their female make-up and attire, they walked into a nearby women’s restroom to see if they could pass as women. When Curtis and Lemmon’s stunt got out to the film crew, they included a similar scene in the film reenacting their antic.


William A. Wellman’s THE PUBLIC ENEMY tells the tale of Tom Powers (James Cagney), a juvenile delinquent that works his way to the top of the Chicago bootlegging underworld. Powers starts his criminal career with childhood friend Matt Doyle (Edward Woods) engaging in petty theft for local crime figure Putty Nose (Murray Kinnell). When Doyle and Powers are involved with a bank robbery gone wrong, Putty Nose abandons them. The duo are recruited by another gang, and slowly work their way from enforcers to big shot bootleggers. When Doyle is gunned downed by a rival gang, Powers becomes hell bent on settling the score. THE PUBLIC ENEMY was nominated for an Academy Award for Best Original Screenplay.


Fun Fact: Hollywood legend has that actress Mae Clarke’s ex-husband claimed to have enjoyed her famous “grapefruit scene” so much that he went to a local theater everyday just to watch that scene.


The Coen brothers’ MILLER’S CROSSING is about Prohibition-era gangster Tom Regan’s (Gabriel Byrne) attempt at keeping peace between two clashing gangs, both of whom seek to control the city’s criminal activity. When mob boss Leo (Albert Finney) and Johnny Caspar (Jon Polito) quarrel over a scheming bookie, Regan tries to settle their discord. However, Regan soon finds himself in a bewildering situation where morals and alliances are relative. The Coen brothers’ MILLER’S CROSSING is sprinkled with rapid-fire dialogue, dark humor and colorful characters.


Fun Fact: While the script states MILLER’S CROSSING takes place in 1929, the feature never specifies in what year it takes place.


On a lighter note, Alan Parker’s BUGSY MALONE is a British musical comedy that illustrates the classic gangster story played entirely by children, including a young Jodie Foster. The musical focuses on Bugsy Malone (Scott Baio), a broke boxing promoter, who gets mixed up with Fat Sam’s (John Cassisi) criminal enterprise. Meanwhile, Malone tries to save enough money to escape the bootlegging underworld with his lover, aspiring singer Blousey Brown (Florrie Dugger). Through using “splurge guns” and cream ball “bullets”, the adorable, Academy Award nominated musical manages to show no real violence.


Fun Fact: When director Alan Parker was looking to cast a child for the role of Fat Sam, he went to a Brooklyn classroom and asked the students who was the worst misbehaved boy in the class. When the class informed Parker that John Cassisi fit his description, Cassisi was immediately hired.