The 10 best Prohibition movies focus on life during the 1920s, when the sale and possession of alcohol was illegal in the United States. This was intended to make America a better place, but instead offered an opportunity for organized crime to flourish by providing illegal alcohol. Prohibition was repealed in 1933, but left a legacy of great gangster films, crime dramas, and even a classic comedy.

  1. “The Public Enemy.” William Wellman’s 1931 crime drama made Jimmy Cagney a star and helped launch the gangster-movie genre. Cagney’s Tom Powers rises up through the ranks of organized crime before meeting a bitter end. The depiction of violence, including the infamous “grapefruit” scene, made the movie controversial for years afterward.

  2. “Little Caesar.” Edward G. Robinson likewise shot to fame as Rico, the “little Caesar” of the underworld. Like Tom Powers, he profited from the clandestine drinking establishments called “speakeasies” that spread far and wide during Prohibition. And like Powers, Rico’s downfall was violent and memorable.

  3. “Scarface.” Real-life gangster Al Capone was the inspiration for this 1932 film starring Paul Muni in the title role. A gang war over rival speakeasies puts Muni in charge of the Chicago mob. The controversial film was remade in 1983 with Al Pacino; the Pacino version also caused controversy for its graphic violence.

  4. “The Roaring Twenties.” Prohibition had been over for six years when this gangster classic appeared in 1939. Legendary tough guys Cagney and Humphrey Bogart co-star as old Army buddies who become rival bootleggers. Their crime career ends just as Prohibition does, in the final days of 1933.

  5. “Some Like It Hot.” Prohibition continued to fuel Hollywood plots long after it was a fading memory. In 1959’s classic comedy, musicians Tony Curtis and Jack Lemmon flee from mobsters after accidentally witnessing a gangland massacre. Donning women’s clothing for disguise, they meet Marilyn Monroe, and try to figure out how to get the girl while getting away from the gangsters.

  6. “The St. Valentine’s Day Massacre.” Aside from inspiring “Some Like It Hot,” the infamous gangland slaying was the subject of its own film in 1967. Legendary director Roger Corman re-created the massacre, in which seven rival gangsters were gunned down by Capone’s mob. Publicity over the killings proved to America that Prohibition was simply not working; it was repealed four years later.

  7. “The Great Gatsby.” The Prohibition era was not all bullets and bloodshed; some folks had a great time during the “Roaring Twenties.” F. Scott Fitzgerald’s legendary novel symbolized the excesses of the time through an immortal character, Jay Gatsby. Robert Redford played the millionaire with a mysterious past in 1974; other versions were released in 1949 and 2000.

  8. “Once Upon a Time in America.” Legendary Western director Sergio Leone turned to the Prohibition era for his final film in 1984. Street kids Robert De Niro and James Woods become New York gangsters thanks to bootlegging and speakeasies. As with many gangsters of the time, real and fictional, the repeal of Prohibition signals the end of their dreams of wealth.

  9. “Miller’s Crossing.” The Coen brothers love old movies, and their films often imitate the styles of previous eras. In 1990, they made their own gangster movie, a loving tribute to the classics of the past. Albert Finney is a Prohibition ganglord manipulated by his right-hand man, Gabriel Byrne.

  10. “The Untouchables.” After remaking “Scarface,” director Brian de Palma made one of the greatest Prohibition films ever, based on the real-life exploits of lawman Eliot Ness. Ness and his incorruptible federal agents square off against bad cops and Capone’s Chicago mob. The film made Kevin Costner a star, and offered plum roles to De Niro, as Capone, and Sean Connery, who won an Oscar.