Top 5 Films About the 1920s

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In the United States, today has the dubious distinction of being Repeal Day, which is the anniversary of the repeal of Prohibition. The 18th Amendment to the Constitution, which had prohibited the sale of alcohol, took effect on January 17, 1920, ushering in the Roaring Twenties, which wound down with the stock market crash of 1929 and fully ended by the adoption of the 21st Amendment on December 5, 1933.

The history of Prohibition and the ’20s have been fodder for period films almost as soon as they ended. In honor of this, let’s legally raise a drink to five favorite movies about the 1920s…

Some Like It Hot1. Some Like It Hot (1959)

This flick has everything. Cross-dressing, gangsters, sexual innuendo, great costumes, witty repartee, musical numbers, and Marilyn Monroe, set in 1929. You can’t ask for more, and you won’t need it. The American Film Institute has named this as the greatest American film comedy of all time, and it’s hard to disagree. The jokes are timeless; makes you think they must have been incredibly risque for ’59 because they’re still pretty racy today (catch that closing line, baby!).

Chicago2. Chicago (2002)

Based on the long-running Bob Fosse musical, this movie is set in 1927 and revolves around a seedy vaudeville/nightclub world as well as prison. The film is jam-packed with stars such as Catherine Zeta-Jones and Renee Zellweger. Costumes are by Colleen Atwood, and she won the Oscar.

The Great Gatsby3. The Great Gatsby  (1974)

Yes, the Robert Redford version, not the more recent Leonardo DiCaprio one. There’s been five of ’em, so you can all pick and choose which film of this book you prefer. I always found that Redford really captured the essence of Jay Gatsby’s beautiful but boot-legging character, and he and Mia Farrow (as Daisy) have great chemistry onscreen. This one won the Oscar for Best Costume too.

The Cotton Club4. The Cotton Club (1984)

An under-appreciated gem of a film, this Francis Ford Coppola creation has a beautiful style that really evokes the period. Hard to go wrong with costumes by Milena Canonero, the Oscar-winning designer of Barry Lyndon and Chariots of Fire before this and Marie Antoinette later. She also designed costumes for Affair of the Necklace.

Singin' in the Rain5. Singin’ in the Rain (1952)

Set during the introduction of “talkie” movies (Al Jolson’s The Jazz Singer was released in 1927), this movie showcases a ton of catchy songs from MGM musical films straight out of 1929 to 1939, and y’know, Gene Kelly dancing and singing in the rain. The American Film Institute rated it the best American musical movie of all time for a reason, dammit. If you don’t love this one, I don’t think we can be friends.

Those are my top five films about the 1920s, what are yours?

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About the author

Trystan L. Bass

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A self-described ElderGoth, Trystan has been haunting the internet since the early 1990s. Always passionate about costume, from everyday office wear to outrageous twisted historical creations, she has maintained some of the earliest online costuming-focused resources on the web. When she’s not dressing up in costumes, she can be found traveling the world with her sweetie and, occasionally, Kendra and Sarah. Her costuming and travel adventures are chronicled on her website, TrystanCraft. She also maintains a popular fashion blog, This Is CorpGoth, dedicated to her “office drag.”

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