14 Best Films Depicting the Roaring '20s

Step back in time to the glamorous era of the 1920s with our curated list of the 14 best films that vividly depict the excitement and exuberance of the Roaring ’20s. From dazzling jazz music to flapper fashion and speakeasy underground culture, these movies capture the essence of this transformative decade in history. Get ready to be transported to a world of glitz, glamour, and societal change as we explore iconic films that bring the Roaring ’20s to life on the silver screen. Join us as we delve into tales of love, ambition, and rebellion set against the backdrop of one of the most captivating periods in the 20th century.

14 Best Films Depicting the Roaring ’20s

The Artist (2011) – IMDb Rating: 7.9
“The Artist” takes us back to the silent film era, offering a nostalgic glimpse into Hollywood during the 1920s. This black-and-white masterpiece follows the story of a silent movie star struggling to adapt to the advent of talkies. With stunning visuals and a captivating storyline, this film beautifully captures the essence of the glamorous yet tumultuous period, showcasing the challenges faced by artists in a rapidly evolving industry. Through its enchanting cinematography and stellar performances, “The Artist” pays homage to the bygone era of classic cinema, making it a must-watch for fans of 1920s history and film buffs alike.
Bugsy Malone (1976) – IMDb Rating: 6.9
“Bugsy Malone” offers a unique twist on the gangster genre by featuring an all-child cast in a prohibition-era setting. Set in the roaring ’20s, this musical comedy follows the rivalry between two gangster factions led by pint-sized mobsters. Filled with catchy musical numbers and comedic performances, the film provides a whimsical take on a typically gritty and violent period in American history. With its clever concept and charming execution, “Bugsy Malone” delivers a delightful and entertaining portrayal of the Prohibition era, making it a standout entry in the 1920s film genre.
The Aviator (2004) – IMDb Rating: 7.5
“The Aviator” offers a biographical glimpse into the life of aviation pioneer Howard Hughes, highlighting his endeavors and eccentricities during the 1920s and beyond. Featuring a stellar performance by Leonardo DiCaprio in the lead role, the film explores Hughes’ ambitious projects, aviation feats, and struggles with mental health issues. Against the backdrop of the glamorous Hollywood and aviation industry of the roaring ’20s, “The Aviator” paints a compelling portrait of an enigmatic figure navigating fame, fortune, and inner demons. With its lavish production design and engaging storytelling, this Martin Scorsese-directed film provides an immersive cinematic experience, capturing the essence of a transformative period in American history.
The Great Gatsby (2013) – IMDb Rating: 7.2
“The Great Gatsby” is a visually stunning adaptation of F. Scott Fitzgerald’s classic novel set in the opulent world of the 1920s. Directed by Baz Luhrmann, this film follows the mysterious Jay Gatsby, played by Leonardo DiCaprio, as he navigates love, wealth, and the American Dream amidst the glittering parties of the Jazz Age. With lavish costumes, elaborate sets, and a modern soundtrack, “The Great Gatsby” captures the essence of the Roaring Twenties in a captivating and extravagant way.
Midnight in Paris (2011) – IMDb Rating: 7.7
“Midnight in Paris” transports viewers back in time to the vibrant cultural scene of 1920s Paris. Directed by Woody Allen, this film follows writer Gil Pender, played by Owen Wilson, as he mysteriously finds himself mingling with iconic figures like F. Scott Fitzgerald, Ernest Hemingway, and Gertrude Stein. As Gil explores the enchanting streets of Paris after midnight, he discovers the allure of nostalgia and the magic of living in the moment. With a mix of fantasy, romance, and wit, “Midnight in Paris” beautifully captures the charm and creativity of the Roaring Twenties.
Chicago (2002) – IMDb Rating: 7.1
“Chicago” is a dazzling musical film that delves into the dark underbelly of the 1920s jazz scene. Set in the era of flappers and prohibition, this movie follows aspiring performer Roxie Hart, played by Renée Zellweger, as she navigates fame, crime, and the pursuit of stardom. With show-stopping musical numbers and intricate choreography, “Chicago” explores themes of corruption, celebrity, and the allure of the spotlight. Nominated for multiple Academy Awards and praised for its electrifying performances, this film offers a mesmerizing glimpse into the tumultuous world of the Roaring Twenties.
The Cotton Club (1984) – IMDb Rating: 6.5
Set in the vibrant world of Harlem during the 1920s, “The Cotton Club” follows the story of a young musician caught in the middle of the jazz scene and organized crime. Directed by Francis Ford Coppola, this film beautifully captures the essence of the era with its stunning musical performances and lavish dance sequences. Featuring a star-studded cast including Richard Gere, Diane Lane, and Gregory Hines, “The Cotton Club” offers a glimpse into the glamorous yet dangerous nightlife of the Roaring ’20s.
Bonnie and Clyde (1967) – IMDb Rating: 7.8
While not set in the 1920s, “Bonnie and Clyde” provides a riveting portrayal of the criminal underworld during the Great Depression, a period closely connected to the Roaring ’20s. This iconic film follows the infamous duo Bonnie Parker and Clyde Barrow as they embark on a crime spree across the central United States. Filled with explosive action sequences and poignant moments, “Bonnie and Clyde” remains a classic depiction of rebellion and romance in the face of adversity.
Some Like It Hot (1959) – IMDb Rating: 8.2
While not a traditional depiction of the Roaring ’20s, “Some Like It Hot” offers a hilarious and entertaining glimpse into the spirit of the era. Starring Marilyn Monroe, Tony Curtis, and Jack Lemmon, this comedy follows two musicians who witness a mob hit and disguise themselves as women to escape the mobsters. Set against the backdrop of a Prohibition-era nightclub, the film captures the glamour, humor, and chaos of the 1920s, making it a timeless cinematic gem loved by audiences for generations.
The Gold Diggers (1923) – IMDb Rating: 7.7
“The Gold Diggers” is a classic silent comedy film that captures the essence of the Roaring ’20s with its extravagant dance numbers and witty humor. The movie follows a group of young women who head to the city in search of wealthy bachelors to marry. Filled with glitzy parties, flapper fashion, and catchy musical sequences, this film provides a delightful glimpse into the glamorous and carefree lifestyle of the era.
Bright Young Things (2003) – IMDb Rating: 6.7
Set in 1930s London, “Bright Young Things” offers a unique perspective on the aftermath of the Roaring ’20s and the impact of the Great Depression. Based on Evelyn Waugh’s novel “Vile Bodies,” the film follows a group of socialites and partygoers as they navigate scandal, romance, and societal change. With its vibrant cinematography and sharp dialogue, this movie beautifully captures the decadence and disillusionment of the post-World War I era.
The Roaring Twenties (1939) – IMDb Rating: 7.9
Starring Hollywood legends James Cagney and Humphrey Bogart, “The Roaring Twenties” is a gripping crime drama that depicts the darker side of the Prohibition era. Set against the backdrop of bootlegging and organized crime, the film follows three friends who become entangled in a dangerous underworld of speakeasies and mobsters. With its thrilling action sequences and compelling characters, this movie offers a thrilling glimpse into the tumultuous and dangerous world of the 1920s.
The Cat’s Meow (2001) – IMDb Rating: 6.4
Set in the 1920s, “The Cat’s Meow” is a drama based on real events surrounding a mysterious death that occurred on William Randolph Hearst’s yacht during a lavish party. The film captures the glitz and glamour of Hollywood’s golden age, depicting the scandalous relationships and power dynamics of the era. With a stellar cast and intricate storytelling, this film offers a glimpse into the extravagant lives of the rich and famous during the Roaring ’20s.
Miss Fisher and the Crypt of Tears (2020) – IMDb Rating: 6.2
“Miss Fisher and the Crypt of Tears” follows the stylish and adventurous Phryne Fisher as she embarks on a journey to unravel an ancient mystery in 1920s British Palestine. This film blends elements of mystery, romance, and adventure against the backdrop of the Roaring ’20s, showcasing the spirit of independence and daring exploration that defined the era. With captivating visuals and a charismatic lead, this movie offers a thrilling escapade through exotic locales and engaging storytelling.