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20 Best Movies Set in the 1920s

They are better known as The Roaring Twenties, The Jazz Age, or The Era of Prohibition. This was an era that was so grand and extravagant that it had a dizzying effect on anyone who got to witness it. This was a period when flappers flaunted their short bob, beads, and glittery knee-length dresses that would sway as they danced to the beats of music and nightlife. The 20s is when there was enough cultural energy, technological innovations, and social revolution to fuel and inspire hundreds of unforgettable movies. They capture an array of themes through speakeasies, jazz clubs, dance halls, and Broadway shows. So here are some of the best movies in the 1920s.

1. The Idle Class (1921)

This is a silent comedy movie from the legendary Charlie Chaplin himself. It is an eccentric film that is not only meant to be enjoyed but also understood and internalized. In this movie, we get to be told the story of a tramp, role played by Charlie Chaplin, who accidentally bumps into a lady who is the aristocratic, role played by Edna Purviance, as she is arguing with her cocktail-winging husband. Soon, matters get to be hilariously confusing when later on, the classy lady mistakes the tramp for her husband and the upper-class golf resort becomes the hub of the most interesting comedy. Chaplin manages to bring out the funny in situations like lost pants, boozing, and fancy-dress balls. The comedy in this movie also pokes fun at the lifestyle the idle rich usually led during the booming 1920s.

2. Bright Young Things (2003)

With ‘Bright Young Things,’ just imagine Gossip Girl which is set in the late 20s and early 30s with the young upper-class socialites from New England but manages to make it richer in themes. It is a lively celebration of the English decadence set in the late 20s right before the country entered into World War 2. In this movie, we follow the story of a young aspiring novelist named Adam Fenwick-Symes, who dreams of marrying a fellow member of society. However, when his very first manuscript is confiscated by customs, he must navigate the dark storm of financial loss, threat, and heartbreak. More impressive in this movie are the costumes, the jazz-fueled parties, and the glittering social worlds of the young rebels.

3. The Cotton Club Encore (2019)

This 2019 movie is a remake of the original one released in 1984, having been based form James Haskins’ 1977 book. The original film was a great hit especially because of how it portrayed the era of show business and gangster life of the 20s. It is also a movie that pays homage to the real-life Harlem jazz club when it was in its prime during the Prohibition Era. This was the era when black musicians played for a white clientele and would constantly go to a club to be seen. In the movie, as the fate of Dix Dwyer and Vera Cicero intertwine, the most populated figures start to unravel this world of glitz and jazz.

4. L’Argent (1928)

Set in 1928, ‘L’Argent,’ is a silent movie that portrays what a society corrupted by greed looks like. The plot is told through the story of a petty thief who has stolen 500 franc notes and the tragedy and ruin that follows because of that one decision. As this money changes hands, lives are also lost, arrests are made and unfortunately, an innocent man who spirals into destitution winds up in jail, getting out to only kill more people. It is indeed a masterpiece movie that blatantly explores themes that at the time weren’t being talked about openly.

5. Pandora’s Box (1929)

In this 1929 masterpiece, an icy and yet very magnetic woman wanders through the streets of Berlin as it thrives into a world of cabarets, movie sets, and very lavish parties. However, none realizes that she is also leaving a trail of destruction wherever she goes. She is known as a feisty woman who deceives and manipulates her wealthy admirers just for pleasure and profit. Well, until she is pushed too far. This movie radiates an energy that isn’t seen often and manages to capture the moral ambiguities of this era through the gaze of Louise Brook’s predatory femme fatale.

6. Bugsy Malone (1976)

Of course, the 1920s were a stylish era that anyone would give anything to go back to. However, what uniquely defines this era was the jazz music that would be played in dim- li clubs and the spread of gangsters everywhere. This 1976 movie is a joyful, musical, crime-comedy set that defies all odds and stars a wonderful cast of all child actors. Bugsy Malone is a troublemaker kid with big dreams and finds himself impressed by the gangster life, machine girls, and showbiz.

7. The Roaring Twenties (1939)

Just like the name suggests, this movie is an amazing tale of American ambition and excess in an era where the prohibition against something wasn’t really viewed as a hindrance but as fuel to the fire of dreams and ambitions. In this movie, James Cagney starts as a very ambitious World War 1 veteran who rises from a small-time bootlegger to a big-time gangster. He has his own gang and the story follows him and his gang as they make fortunes in booze, luring women and establishing rackets while still showing off their status and wealth in high-end night clubs.

8. The Artist (2011)

In this 2011 movie set in the 1920s, George Valentin, a silent movie superstar finds out his world has been turned upside down with the arrival of the ‘talkies,’ during the late 20s. On the other hand, Peppy Miller once infatuated with Valentin, ends up becoming a famous movie star. He fights to retain his fame and ambition and soon, the quick way to stardom starts feeling unsettling. The beauty of this movie is how it is set against the very vibrant backdrop of the Jazz Age, hence giving way to the Great Depression era. This movie is indeed a nostalgia, especially for those yearning for much greater things.

 9. The Cider House Rules (1999)

The movie is, plainly put, a phenomenal piece of art that has starred iconic actors like Charlize Theron, Tobey Maguire, Michael Caine, and also Kathy Baker. It tells the story of the journey of an orphan boy from a secluded boys’ home in Maine to the heart of New Jersey. It is a very dramatic film that just impresses you from the word go and what it means to grow up and shedding off all naivety that perhaps you have been shielded from for a long time. It is a perfect coming-out-of-age movie.

10. Midnight in Paris (2011)

In this movie, we get to be introduced to Woody Allen, a guy who paints an aesthetically pleasing and visually stunning fantasy comedy. This comedy revolves around a character named Gil, an American screenwriter who has had a big fascination and yearning for Paris in the 1920s. As he is on vacation with his fiancee, he finds himself magically transported back to the city every time the clock strikes 12. The back and forth as he tries to understand it all is what the movie is grounded on and what makes it worth the watch. It is simply put, quite a masterpiece.

11. Some Like It Hot (1959)

This is a madcap comedy movie that was co-written, directed, and produced by Billy Wilder. It tells the story of two musicians who unfortunately are at the wrong place, at the wrong time. They witness accidentally a mob hitting and they subsequently have to disguise themselves as women in order to hide from mobsters. This 1959 movie follows their wild adventures as they join an all-female jazz band while on a trip to Florida. More than anything else, this movie is hilarious and will definitely make you chuckle one or two times at the very least.

12. Chicago (2002)

This is another comedy-drama set in the roaring prohibition era of the 1920s. ‘Chicago,’ follows the story of two female murderers, who find themselves locked up and are awaiting trial. They both vie for the attention of Chicago’s most notorious and slickest criminal lawyer, so as to improve their chances of being acquitted. This film has been done so meticulously and cleverly that it won an Academy Award for Best Picture. Furthermore, it clearly showcases the lavish sets of the 20s, the undisputed choreography, and glitter-filled superficiality.

13. Babylon (2022)

This 2022 movie is the most recent epic drama that is set amidst the cultural renaissance of the early 1920s in London. The film shows different characters that come from different fringes of society during a time when Hollywood was transitioning from the silent era to the novelty world of sound films. This movie also stars some of the most iconic actors in Hollywood and brings to the table a more mature examination of the complete legacy of class divide and total exclusivity.

14. Singin’ in the Rain (1952)

To be blunt, this is the most beautiful classic romance that has ever been made (of course that is purely a biased opinion). It has adopted so well the theme of musical comedy and the sublime art of storytelling. It is a timeless masterpiece that triumphs over technological upheavals. Set in the late 1920s Hollywood, when it was moving from silent to talkies, this film showcases the chaotic lives of two individuals, caught up in this change. It is packed with many musical numbers and eye-catching choreography which makes the movie one you don’t want to miss out on.

15. The Great Gatsby (2013)

This 2013 film, starring the legendary Leo Di Caprio is an opulent but tragic portrayal of the Jazz Age, inspired by Scott Fitzgerald’s book of the same name, published in 1925. It effectively describes the story of Jay Gatsby and the lavish balls and parties conducted in his mansion on Long Island. What’s even more beautiful about this movie is how it has beautifully combined classic and modern eras of a completely different era.

16. The King’s Speech (2010)

In this 118-minute-long movie, we get to acquaint ourselves with the tale of King George VI and his unexpected ascension to the throne of the British Empire. This was in 1936. King George had a stammering problem and this movie depicts so clearly the hurdles he went through to try and overcome it and the speech therapist who helped this unsure monarch overcome his stammer and gain the confidence that was needed to run a whole monarch. It is worth the watch if you are a history buff.

17. Changeling (2008)

Released in 2008, this is a biography and crime/drama movie that is not only interesting but touching. In the movie, the son of a character named Christine goes missing. She reached out to the LAPD for help but they tried to pass off an imposter as her son so as to quiet down the public outrage and protests. She refuses to accept and fights to find her son. Starring the iconic Angelina Jolie, this is one movie that will for sure impress you from the word go and make you obsessed with the 1920s culture.

18. The Cat’s Meow (2001)

Released in 2001, this is a semi-true story of the famous Hollywood murder that occurred at a star-studded gathering while aboard William Randolph Hearst’s yacht in 1924. This film has captured well the events of that night although, of course, it has added a bit of its own drama to make it even more interesting.

19. The Painted Veil (2006)

This movie is both romantic and sad and that is probably what makes it even more beautiful. A character by the name, of Dr. Walter, marries a beautiful woman named Kitty. Sadly, he finds out she is cheating on him and gives her an ultimatum to join him as he heads to China to fight a dreaded disease that is spreading in a small village or join her lover. The storm they overcome together as a couple and the losses they incur make the movie so emotional and relatable.

20. La Vie En Rose (2007)

In this biography movie, we get to learn more about the iconic and talented French singer, Edith Piaf. She was raised by her grandmother in a brothel and was discovered while singing on a street corner at the age of 19. Despite her success, however, her life was filled with so much tragedy and this movie does an amazing job in getting most of the facts right. Directed by Olivier Dahan, this is another must-watch movie set in the 1920s.

The 20s were an interesting era as a lot of transitions both in the entertainment industry and life in general were taking place. This is the era that distinguished and shaped most of the pop culture we have adopted in this modern era.