Movies Like The Mad Twenties

If you liked The Mad Twenties (1964), a movie, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Yankee Doodle Dandy (1942)
★ 7/10
A film of the life of the renowned musical composer, playwright, actor, dancer and singer George M. Cohan.
2
Valentino (1977)
★ 5.8/10
The untimely death of silent screen star Rudolph Valentino prompts the many women in his past to reminisce about his troubled rise to superstardom.
3
The Great Gatsby (2013)
★ 7.3/10
Nick Carraway arrives in New York in 1922, an era of loose morals, glittering jazz and bootleg kings. Chasing his own American Dream, Nick encounters the mysterious millionaire Gatsby and his bewitching cousin Daisy…
4
The Cat's Meow (2002)
★ 5.8/10
Semi-true story of the Hollywood murder that occurred at a star-studded gathering aboard William Randolph Hearst's yacht in 1924.
5
To Wong Foo, Thanks for Everything! Julie Newmar (1995)
★ 7.5/10
Veteran drag queens Vida Boheme and Noxeema Jackson take novice Chi-Chi Rodriguez under their wing on a madcap road trip across the country to compete in the Drag Queen of America pageant in Los Angeles.
6
Young Woman and the Sea (2024)
★ 7.8/10
This is the extraordinary true story of Trudy Ederle, the first woman to successfully swim the English Channel. Through the steadfast support of her older sister and supportive trainers, she overcame adversity and the…
7
Bullets Over Broadway (1994)
★ 7.1/10
After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a…
8
Hoodlum (1997)
★ 6.5/10
In 1934, the second most lucrative business in New York City was running 'the numbers'. When Madam Queen—the powerful woman who runs the scam in Harlem—is arrested, Ellsworth 'Bumpy' Johnson takes over the business and…
9
Paris Is Burning (1991)
★ 8/10
Where does voguing come from, and what, exactly, is throwing shade? This landmark documentary provides a vibrant snapshot of the 1980s through the eyes of New York City's African American and Latinx Harlem drag-ball…
10
Now and Then (1995)
★ 6.9/10
Waxing nostalgic about the bittersweet passage from childhood to puberty, four childhood girlfriends — Teeny, Chrissy, Samantha and Roberta — recall the magical summer of 1970. During their walk down memory lane, they…
11
Diggers (2007)
★ 6/10
In 1976, four working-class friends come of age in The Hamptons, on the South Shore of Long Island, New York, as clam diggers, as were their fathers and their grandfathers before them. They must cope with and learn to…
12
Radio Days (1987)
★ 7/10
The Narrator tells us how the radio influenced his childhood in the days before TV. In the New York City of the late 1930s to the New Year's Eve 1944, this coming-of-age tale mixes the narrator's experiences with…
13
Cradle Will Rock (1999)
★ 6.5/10
A true story of politics and art in the 1930s USA, centered around a leftist musical drama and attempts to stop its production.
14
There's No Business Like Show Business (1954)
★ 6.1/10
Molly and Terry Donahue, plus their three children, are The Five Donahues. Youngest son Tim meets hat-check girl Vicky and the family act begins to fall apart.
15
Beast (2018)
★ 6.5/10
A troubled woman living in an isolated community finds herself pulled between the control of her oppressive family and the allure of a secretive outsider suspected of a series of brutal murders.
16
Thoroughly Modern Millie (1967)
★ 6.9/10
Millie Dillmount, a fearless young lady fresh from Salina, Kansas, determined to experience Life, sets out to see the world in the rip-roaring Twenties. With high spirits and wearing one of those new high hemlines, she…
17
Hello, Dolly! (1969)
★ 7/10
Dolly Levi is a strong-willed matchmaker who travels to Yonkers, New York in order to see the miserly "well-known unmarried half-a-millionaire" Horace Vandergelder. In doing so, she convinces his niece, his niece's…
18
Singin' in the Rain (1952)
★ 8.1/10
In 1927 Hollywood, a silent film star falls for a chorus girl just as he and his paranoid screen partner struggle to make the difficult transition to talking pictures.
19
The Last Days of Disco (1998)
★ 6.3/10
Two young women and their friends spend spare time at an exclusive nightclub in 1980s New York.
20
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.