Whenever award season comes around each year, a joke is commonly made: Hollywood loves movies about itself. Ever since the birth of the film medium, acting for the screen has increasingly become more lucrative, and some of the wildest stories about actors, directors, and the scandals associated with making a movie into a reality have become a part of the lore of Hollywood. While some of these movies have barely managed to see the light of day, others have become celebrated as a form of artistry in the industry and mainstream media.
But if there’s one decade that certainly shines in the world of film, it’s the 1920s. Many of the movies made about the decade are now period pieces, made almost 100 years after the fact — a certain brand of nostalgia that has a tendency to ruminate on the period between silent films and the talkies. As some actors were forced to fade into obscurity, their talents solely deemed useful for the period of silent films, others found new fame as actors before the rise of the Hays Code. For those looking to dig deeper into the period, here are 10 movies about 1920s Hollywood you should watch at least once.
10 Some Like It Hot (1959)
Some Like It Hot
- Release Date
- March 29, 1959
- Director
- Billy Wilder
Marilyn Monroe, Tony Curtis, and Jack Lemmon all star in the hit Some Like It Hot, which came out in theaters all the way back in 1959. The movie opens in Chicago at the tail-end of the decade, with the two male characters working as musicians within the entertainment industry. Starting out at a speakeasy, they meet an all-women band, and decide to head out on the road to get away from the gangsters chasing after them.
A Classic Film About Hollywood
With a twist about the entertainment industry, Some Like It Hot has become a classic for a reason. One of Monroe’s most iconic roles, it certainly has earned its place in American cinema for being one of the more notable films of the '50s. In particular, the film has struck a chord with LGBTQ+ audiences, who see it as a seminal film made during a time of heavily conservative values. Stream on Max
9 Babylon (2022)
Babylon
- Release Date
- December 23, 2022
- Rating
- R
Damien Chazelle’s Babylon was released in 2022 to mixed reviews. A three-hour saga about the introduction of talkies into the film industry, Chazelle’s camera focuses on a set group of actors trying to make it in the industry. With wild parties and opportunities coming out of every corner at first, their glory might only be fleeting as Hollywood tries to leave them behind in search of something greater.
Why It’s Great
Babylon certainly has its downsides, but the film does an excellent job of capturing the spirit of the period it’s depicting, tackling themes of dreams, survival, race, and class. With gorgeous cinematography and some of the most lavish scenes in the past decade, it’s worth watching on a Friday movie night at least once to try it out. Stream on MGM+
8 The Cat’s Meow
Kirsten Dunst starred in The Cat’s Meow in 2001, which tells a story that has become little known in history throughout recent years. On a November day in 1924, several influential figures, from a silent film star to a publishing titan, go out for a ride on a yacht. When the filmmaker Thomas H. Ince is mysteriously shot aboard the ship, it leads the film towards unraveling the motivations behind killing someone who was so big in the industry.
Why It’s Great
The Cat’s Meow tackles lore from the early-1920s, when the silent film industry was at its height. Although the film might not exactly be a work of art, it still proves to be quite entertaining throughout its run time. More than anything, Dunst was at the height of her career during this film's release, and The Cat's Meow proved her versatile talents. Rent on Prime Video.
7 The Artist (2011)
A black and white film inspired by silent movies released in 2011, The Artist has become one of the more well known movies about the period in recent years. Spanning five years, beginning in 1927, The Artist is about a silent film star and a young woman who rises to prominence after literally bumping into him. However, with the introduction of talkies in Hollywood, everything is about to change for them both.
Why It’s Great
Few modern movies have taken the approach of silent films in the past few decades, and The Artist shows why it’s still a coveted art form when done right. It’s a brilliant movie, a technical achievement, and with a solid storyline, it becomes one of the greatest movies released during the 2010s. In fact, it won three of the Big Five Oscars: Best Picture, Best Director (for Michel Hazanavicius), and Best Actor (for Jean Dujardin). Stream on Max
6 Chaplin (1992)
Chaplin
- Release Date
- December 17, 1992
- Rating
- PG-13
Once one of the most famous actors in the world, Charlie Chaplin’s legacy still lives on today, and the movie Chaplin tackles the subject of his life. Robert Downey Jr. stars as Chaplin, as he recalls his rise from the slums of London to becoming a beloved actor. Starting at the age of five, he began a life on the stage, propelling him towards a destiny that seemed inescapable at times.
Why It’s Great
An early work of Downey Jr., Chaplin shows him in his element, although it comes across as a more standard biopic throughout its run. For those interested in learning more about the actor, this movie offers an excellent alternative from the books. For his performance, Downey earned his first Oscar nomination for Best Actor. Stream on MGM+
5 The Aviator (2004)
The Aviator
- Release Date
- December 17, 2004
- Rating
- PG-13
One of Leonardo DiCaprio’s more prominent roles in the 2000s was in The Aviator, which hit American theaters in 2004. Directed by Martin Scorsese, DiCaprio portrays the Hollywood director Howard Hughes, whose mental illness and obsession with aviation led him to become a big figure in the aviation industry while staying active in Hollywood. While balancing these two worlds, his OCD continues to worsen, leading to erratic behavior from Hughes.
Why It’s Great
The Aviator is not only an excellent period piece, but it shows how one powerful individual succumbs to the effects of obsession and mental illness. As he straddles two different worlds, it offers a tribute to one of the bigger figures during the Golden Age of Hollywood. Stream on Paramount+
4 Singin’ in the Rain (1952)
Singin’ in the Rain is one of the most well-known movies set during the 1920s, and it, too, grapples with the impact of talkies on the industry. Released in 1952, it transports viewers back into the late-20s as talkies are first being implemented through the perspective of three actors working in the industry. The film is now considered one of the best movies ever released.
Why It’s Great
While a movie like Babylon goes hard into the ramifications of talkies on silent stars, Singin in the Rain is more accessible due to how it utilizes a lighthearted approach to the subject. With a musical element, it’s really hard not to love a movie like Singin’ in the Rain. Indeed, when one thinks of classical Hollywood cinema, this film, more often than not, comes to mind. Stream on Max
3 Hollywood Story (1951)
In Hollywood Story, which came out during the '50s, the main character is a hotshot in New York City’s theater scene, who wants to cross the country and form his own Hollywood studio. He does just that and purchases an old studio, becomes inspired by the murder of a famous director in the '20s, and then decides to make a movie about the subject. However, this puts him in danger in unexpected ways.
Why It’s Great
Those who like a movie within a movie structure will enjoy how Hollywood Story utilizes this approach to tell a story within this decade, although it’s technically a '50s-based movie. Inspired by the murder of William Desmond Taylor, Sunset Boulevard fans would definitely appreciate this movie. Not Currently Available to Stream or Purchase
2 You’re My Everything (1949)
Released in 1949, You’re My Everything is one of those movies that has been overshadowed by the other great movies of the decade. A musical directed by Walter Lang, the film opens in 1924, when a young woman, Hannah, waits outside a theater to meet the star of the musical she saw: Tim O’Connor. The two end up falling in love, and together they go to a Hollywood screen test. But when she gets the part over him, she becomes a silent film star in the industry, and, as she retires, their daughter is looped into a three-contract deal with a studio.
Why It’s Great
Although You’re My Everything isn’t structurally sound when it comes to plot and characters at some moments, it offers an interesting take on Hollywood in the 1920s and beyond: the actors are stuck in contracts they can’t get out of. As it threatens to destroy the main characters’ family, they have to navigate entirely new waters throughout the movie. Not Currently Available to Stream or Purchase
1 Make Me a Star (1932)
Pre-Code movies deserve more love in film history, and Make Me a Star is one of these forgotten gems. Merton is a small-town boy with stars in his eyes, as he wants to find a career as an actor in the movies. He comes to Hollywood to study acting, and when he gets his opportunity to audition and get a spot in a Western, he screws up his one line, getting him fired. But this won’t be the last of him in the industry if he can’t help it.
Why It’s Great
Many can relate to the aspirations of the main character in Make Me a Star, as well as messing up what might be his only chance. We all love a good underdog story, and that’s what Make Me a Star ultimately becomes, even if his dream shifts halfway through the film. Not Currently Available to Stream or Purchase
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