1920s Flicks

Marilyn Monroe starred in Some Like It Hot in 1959.

The 1920s were wrought with flappers, gangsters, Prohibition, three-piece suits, The Great Gatsby and so much more that has easily made the decade a fan favorite for fashion, literature and movies alike. Check out our picks for the best films based on the 1920s.

Some Like It Hot

Marilyn Monroe did quite a nice job of portraying Sugar, a singer in an all-girl jazz band from the ’20s, who exudes sweetness and of course, sex. After witnessing a Mafia murder in Chicago, saxophone player Joe (Tony Curtis) and Jerry (Jack Lemmon), improvise an escape plan. They decide to disguise themselves as women and join Sugar and her all-female jazz band on their way to Florida. Impersonating a millionaire while trying to find love and keeping the mobsters at bay makes for some great comedy in this 1959 film.

The Great Gatsby

Whether you prefer Robert Redford’s Jay Gatsby and Mia Farrow’s Daisy Buchanan (1974) or Baz Luhrmann’s version with Leonardo DiCaprio and Carrie Mulligan (2013), both films depict F. Scott Fitzgerald’s Long Island tale of the summer of 1922. The Great Gatsby epitomizes the ’20s, filled with Long Island Gold Coast wealth, glamorous parties, jazz music, pure romance and the American Dream.

The Artist

The first silent film in decades, which went on to win several awards including the Best Picture Academy Award in 2012, 2011’s The Artist was a black and white dramedy of epic proportion. Starring Jean Dujardin as George Valentin and Bérénice Bejo as Peppy Miller, the film takes place in Hollywood between 1927 and 1932, and focuses on the relationship of silent film star George Valentin and the rising young actress Peppy Miller as silent cinema slowly becomes replaced with talkies.


Midnight In Paris

Who would turn down the chance to hang out with Ernest Hemingway and Pablo Picasso? Gil Pender (Owen Wilson), a screenwriter and aspiring novelist, is vacationing in Paris with his fiancée (Rachel McAdams), when he decides to tour the city alone. One night, Gil goes back in time, for a night with the Jazz Age’s icons of art and literature. The more time Gil spends in the past, the more he dislikes the present. Woody Allen enlists Marion Cotillard, Michael Sheen, Tom Hiddleston and Kathy Bates, all of whom are “borne back ceaselessly into the past.”


The classic tale of a New York mobster, what the ’20s were mostly about. The 1991 version of the film stars Warren Beatty as Benjamin “Bugsy” Siegel, who leaves New York City for the glamour of Hollywood, CA. Taken aback by actress Virginia Hill (Annette Bening), the two begin a courtship, despite Siegel having a wife and children. Obsessed with creating a gambling empire, Siegel helps develop Las Vegas, only to find himself in big trouble over his construction of the Flamingo Hotel.


Pop, six, squish, uh-uh, Cicero, Lipschitz. Back in 2002, Chicago went from Broadway to the silver screen. When nightclub sensation Velma (Catherine Zeta-Jones) murders her unfaithful husband and housewife Roxie (Renée Zellweger) winds up in prison alongside her, Chicago lawyer Billy (Richard Gere) takes on both cases. The events turn the city into a media frenzy during Chicago’s Jazz Age as the women fight for fame and attention.

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Jennifer Fauci
Jennifer Fauci is the former managing editor of Long Island Weekly, Anton Media Group's award-winning special sections and Anton’s local magazines. Her passion for literature, travel and the arts lend to the unique content in her publications. In her time at Anton, she has received first place in the Folio Awards, second place for the NYPA awards and is the recipient of six PCLI awards.

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