It's one thing for a movie to be set during the 1920s. It's another thing for a movie to truly express the spirit of the Roaring Twenties.
Also known as the Jazz Age, the 1920s decade was a rip-roaring time for artists, musicians, and the upper class, who danced the night away without corsets or chaperones.
Back then, city life boomed, morals grew more flexible, and the backfiring of Prohibition made everyone drink even more.
Here are the greatest movies set during the Roaring Twenties that successfully capture the razzle dazzle of an era crowded by flappers, champagne, and Louis Armstrong.
15. Bright Young Things (2003)
Directed by Stephen Fry
Starring Stephen Campbell Moore, Emily Mortimer, Dan Aykroyd
Comedy, Drama, War (1h 42m)
Before the 1920s, women were expected to go straight from high school to housewife, bypassing the college parties and rebellions of today. The youngsters in Bright Young Things defy these expectations during a time when defiance was far from the norm.
Seemingly petrified of boredom, the London bohemians sniff and gossip their lives away, diving headfirst into the early nightclub scene. Of course, this kind of lifestyle isn't sustainable, and before they know it World War II comes swooping in.
Bright Young Things distills the magic of their outrageous lives before it's all snuffed out. British comedy legend Stephen Fry directs this chaotic coming-of-age tale about these characters' reckless lives.
14. Bullets Over Broadway (1994)
Directed by Woody Allen
Starring John Cusack, Jack Warden, Chazz Palminteri
Comedy, Crime (1h 38m)
The 1920s and 1930s are clearly Woody Allen's favorite decades from the look of his filmography. Magic in the Moonlight, Midnight in Paris, Café Society, Sweet and Lowdown, Shadows and Fog, and, of course, Bullets Over Broadway are just some examples.
John Cusack stars in this Oscar-winning Woody Allen movie where black comedy meets crime. Beyond cinema, theater was also undergoing a 1920s boom, most notably on Broadway.
Playwright David Shayne (played by John Cusack) is bright-eyed and full of hope when he leaves Pittsburgh for the big city. Trouble is, he can't find the proper financing... except from a gangster who wants to cast his talentless girlfriend.
13. Babylon (2022)
Directed by Damien Chazelle
Starring Brad Pitt, Margot Robbie, Jean Smart
Comedy, Drama, History (3h 9m)
What was 1920s America all about? Parties and cinema! Well, in the cities, at least. In the early 1920s, Hollywood was budding as a wealthy municipality where movies were made, and by the end of the decade, it was thought of in the same way it is today.
Damien Chazelle focuses on the film industry to show how quickly times changed during the Roaring Twenties. The evolution of silent film to sound is representative of this.
Babylon doesn't feel nearly as humdrum as its description sounds. Instead, we have magnificent party scenes soaked in sweat and glitter, where Margot Robbie dances at 100 mph opposite Brad Pitt.
Hollywood and gangsters went hand-in-hand during the 1920s, and starlets killed themselves on champagne, drugs, and gambling. Babylon is truly a lesson in excess.
12. Bugsy Malone (1976)
Directed by Alan Parker
Starring Jodie Foster, Scott Baio, Florence Garland
Comedy, Crime, Family (1h 33m)
There are two big subjects that come to mind when thinking about the 1920s: jazz and gangsters. That's Bugsy Malone.
A fun night of dancing and cold-blooded murder might sound incongruent, but the two often merged together as gangsters flaunted their riches and carried out crimes under the cover of nightlife.
Bugsy Malone takes all this and gives it an unexpected spin—by having all the characters played by kids. Mobsters, dancers, and broads are all played by children under the age of 16, introducing newcomers like Jodie Foster.
Between the splurge outs and Speakeasies, you'll find fun musical numbers that made Bugsy Malone so memorable. Alan Parker wrote and directed his knockout feature debut that won three Academy Awards.
11. La Vie en Rose (2007)
Directed by Olivier Dahan
Starring Marion Cotillard, Sylvie Testud, Pascal Greggory
Biography, Drama, Music (2h 20m)
The 1920s were mostly Roaring in two places: Paris and Hollywood.
England was snobby, class-rigid, and still recovering from the Great War. Italy was stuck in the Red Years under the eye of Benito Mussolini. But in Paris? Everything was shimmering.
Édith Piaf was a symbol of France during its most iconic decade, when the Café Society was still famously kicking about. She was a cabaret singer who specialized in chanson réaliste, enchanting the world with her powerful voice.
But while Piaf seemed like an emblem of grand stages and jazzy nightclubs on the surface, she actually led a tragic life.
In the performance of a lifetime, Marion Cotillard depicts Piaf's rise from a childhood spent on streets and in brothels to her fall into drug addiction and an early death.
10. The Aviator (2004)
Directed by Martin Scorsese
Starring Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale
Biography, Drama (2h 50m)
Real-life billionaire Howard Hughes was all about the big and the grand—two descriptors that perfectly fit the 1920s.
Hughes didn't rest until he'd made the most expensive film at the time (Hell's Angels), or until he broke the speed record for flying around the world (in four days). And after that, he just kept going!
That is, until his crippling OCD got the better of him.
Martin Scorsese and Leonardo DiCaprio teamed up (again) to bring Howard's biopic to life. The Aviator is as epic in proportion as Howard was, and indeed the era itself.
Flashing cameras, zooming planes, and the buzz of new "talkies" give us a feel for the 1920s Hollywood atmosphere. Even the color grading matches the times, using two-strip Technicolor for historical accuracy.
9. The Cotton Club Encore (2019)
Directed by Francis Ford Coppola
Starring Richard Gere, Gregory Hines, Diane Lane
Crime, Drama, Music (2h 19m)
Why were the Mafia suddenly so prominent in the 1920s? Prohibition, of course! They knew how to profitably smuggle drugs and alcohol, and they knew how to handle violent, criminal, and corrupt elements.
The Cotton Club was a real Harlem nightclub that was more lenient on segregation rules than most jazz joints. A lot of money went into bringing this legendary spot to life, which served as a revolving door for gangsters, businessmen, dancers, lovers, addicts, musicians... the lot.
When The Cotton Club was originally released in 1984, director Francis Ford Coppola made some serious changes to its structure due to meddling from distributors—changes that put more focus on the white characters, less on the black characters.
In 2019, Francis Ford Coppola released a restructured version, this time titled The Cotton Club Encore, that restored much of his original vision and resulted in a much stronger, revelatory film.
8. The Artist (2011)
Directed by Michel Hazanavicius
Starring Jean Dujardin, Bérénice Bejo, John Goodman
Comedy, Drama, Romance (1h 40m)
Modern films still like to dabble in that old black-and-white look, whether to fit a vintage setting or simply to look stylish.
The Artist uses monochrome for both reasons, mimicking a silent "part-talkie" from the 1920s. Michel Hazanavicius's French movie might lack in color, but it's more than made up for with humor, pathos, and dreams. Enough to win multiple Oscars, anyway!
While Howard Hughes was wincing down the red carpet at the TCL Chinese Theatre, Peppy Miller (played by Bérénice Bejo) was trying to make it big in Hollywood as the 1920s drew to a close.
The Artist is a spectacle movie in a different way—not with superpowers and explosions, but with jazzy dance-offs. Hazanavicius pleases both crowds and critics with a comedy-drama full of substance and style.
7. Chaplin (1992)
Directed by Richard Attenborough
Starring Robert Downey Jr., Dan Aykroyd, Geraldine Chaplin
Biography, Comedy, Drama (2h 23m)
Like The Aviator, Chaplin doesn't take place exclusively in the 1920s because it's a biopic of one man's entire life from start to finish. However, Charlie Chaplin is most associated with the 1920s because that's when he rose to fame and changed cinema forever.
After co-founding United Artists in 1919 and making groundbreaking silent features like The Kid in 1921, Chaplin became renowned for his gags and comedic timing.
But that wasn't all. The Buster Keaton-type figure added drama and pathos to his slapstick comedies (which had never been done before), which took him on a path to becoming the richest man in America.
Richard Attenborough shows us the man behind the laughter—from his poor childhood to creating his famous The Tramp alter-ego—who's perfectly embodied by Robert Downey Jr.
6. Chicago (2002)
Directed by Rob Marshall
Starring Renée Zellweger, Catherine Zeta-Jones, Richard Gere
Comedy, Crime, Musical (1h 53m)
Do you like jazz? Musicals? Feminism? Then Chicago is for you! But don't sweat—this isn't a cheesy, happy-go-lucky musical. It's full of fierce women getting bloody revenge on their trashy men.
Set in 1924, Chicago blends film with theater, which isn't unusual given that it's based on the 1975 show scored by John Kander (itself originally written in 1926 by Maurine Dallas Watkins).
In Chicago, the leading ladies are awaiting trial for murder when a slimy lawyer comes to save them.
Chicago both glamorizes and criticizes the scandals and corruption of Chicago's underbelly where Billy Flynn (played by Richard Gere) turns his clients into celebrities for publicity—to good and bad results.
5. Changeling (2008)
Directed by Clint Eastwood
Starring Angelina Jolie, John Malkovich, Jeffrey Donovan
Biography, Crime, Drama (2h 21m)
Away from the glamour of the Jazz Age, Changeling gives us a true account from the darker side of the era.
Sure, flappers were out defying gender rules, but that didn't mean women were being treated fairly. In 1928, the missing son of Christine Collins (played by Angelina Jolie) was found and returned to her by the police. Except, he wasn't her son.
Deemed hysterical and delusional for not recognizing her own child, Christine is sent to a psychiatric ward. There, she meets other imprisoned women who spoke out against corrupt authority.
The fact Clint Eastwood's critically acclaimed film really happened is sort of horrifying to learn. And it didn't happen in the rural boonies. This all took place in the "progressive" city of Los Angeles!
4. The Great Gatsby (2013)
Directed by Baz Luhrmann
Starring Leonardo DiCaprio, Tobey Maguire, Carey Mulligan
Drama, Romance (2h 23m)
Director Baz Luhrmann loves to blend the old with the modern, like in his 1997 version of Romeo and Juliet (Romeo + Juliet) where gangsters recite Shakespeare while wearing Hawaiian shirts.
Lurhmann's second collaboration with Leonardo DiCaprio, The Great Gatsby, takes place in the glittering summer of 1922, where wannabe writer Nick Carraway (played by Tobey Maguire) meets the elusive millionaire Jay Gatsby (played by Leonardo DiCaprio).
Every week, Gatsby's mansion hosts all of New York for his famed extravagant parties. But what's his real motive?
The Great Gatsby was written by one of the most influential writers of the decade: F. Scott Fitzgerald. Writing from the time and his own experiences, Fitzgerald captured the essence of the 1920s so we can learn more about it than what fact-based history books tell us.
3. Midnight in Paris (2011)
Directed by Woody Allen
Starring Owen Wilson, Rachel McAdams, Kathy Bates
Comedy, Fantasy, Romance (1h 34m)
Midnight in Paris was one of Woody Allen's dwindling final imprints on cinema before old age and dodgy accusations took him off the A-list. It's also one of the few time travel movies that isn't a sci-fi thriller.
Instead, Midnight in Paris is a nostalgic ode to the Golden Age, even if everyone has different ideas of what "golden age" means. For aspiring novelist Gil Pender (played by Owen Wilson), it means 1920s Paris. For others, it's the Belle Époque or maybe the Renaissance.
Gil Pender is the type who likes to walk in the rain. One of his midnight strolls causes him to tumble back in time, where he meets famed names of the past, including Ernest Hemingway, Zelda and Scott Fitzgerald, and Salvador Dalí.
Midnight in Paris will make you sentimental about a time you've never even lived in, as the movie itself serves as the slice of memorabilia that Gil Pender is always searching for.
2. Singin' in the Rain (1952)
Directed by Stanley Donen and Gene Kelly
Starring Gene Kelly, Donald O'Connor, Debbie Reynolds
Comedy, Musical, Romance (1h 43m)
Being the Jazz Age, there was a lot of music going on in the 1920s. It makes sense that so many musicals are set in this era!
Tap dancing and Hollywood films were all the rage, especially with the release of the first sound movie The Jazz Singer in 1927. When Monumental Pictures (a fictional version of MGM) is threatened by this new technology, they decide to make their own "talkie."
In fact, the studio takes it one step further, showing us the year when "talkies started to sing." The movie-within-a-movie features Gene Kelly as a silent movie star who turns out to have a great singing voice.
Everything about Singin' in the Rain is vibrantly abundant and is still one of the most famous musicals, even seven decades later! Gene Kelly directed and choreographed the hit alongside Stanley Donen.
1. Some Like It Hot (1959)
Directed by Billy Wilder
Starring Marilyn Monroe, Tony Curtis, Jack Lemmon
Comedy, Music, Romance (2h 1m)
Marilyn Monroe was the sex symbol of the 1950s, and Some Like It Hot arrived just in time for censorship boards to give movies more leeway. Although not at all explicit by today's standards, its innuendos had audiences blushing and laughing at the same time.
Set in the gangster hotbed of 1920s Chicago, two jazz musicians get mixed up with the mob and have to cross-dress to stay safe.
That's where Monroe comes in as the sensual performer Sugar Kane. Both men compete for her affection while maintaining their disguises, plunging into a quick-witted crime comedy.
Billy Wilder had already made a name for himself with Sunset Boulevard (1950), and Some Like It Hot only earned him even more Oscar nominations. Luckily, both films still hold up today.
