25 best Prohibition movies

Once Upon a Time in America (1984)

Sergio Leone, famous for his spaghetti westerns, yearned to make a trilogy set in America – but ended up making one incredibly long (229 minutes) movie. Telling a tale of Jewish New York gangsters that spanned 50 or so years, Once Upon A Time In America is widely regarded as Leone’s masterpiece – and Roger Ebert once called it the best film depicting the Prohibition era ever made.

Some Like It Hot (1959)

Prohibition wasn't all about booze and bullets – this 1959 screwball comedy found plenty of humour in, er, gangland massacres. Tony Curtis and Jack Lemmon's struggling jazz musicians are forced to drag up and go into hiding after witnessing the St Valentine's Day Massacre – but it's not all bad news, since they become bosom buddies with Marilyn Monroe's Sugar Kane.

The St. Valentine’s Day Massacre (1967)

Al Capone is back – here played by Sam Robards – in this drama based on the 1929 gangland killing that shocked America. Director Roger Corman originally wanted to cast Orson Welles in the role of Capone, only for 20th Century Fox to veto the deal due to Welles’ well-earned reputation as a diva and maverick.

The Great Gatsby (1974)

Perhaps not one of the first movies you think about when someone mentions prohibition, The Great Gatsby gives a very different view of 1920s America than the average gangster thriller. But Robert Redford’s Gatsby, of course, made his fortune through bootleg liquor, allowing him to throw his lavish Long Island parties – but also preventing him from gaining the true American upper class status he craves.

The Public Enemy (1931)

James Cagney has probably played more gangsters than anybody, and this movie (actually made during Prohibition) saw him at his menacing best as a young hood rising through the ranks of a bootlegging empire. Jean Harlow stars as his love interest.