Best Charlie Chaplin Movies for Classic Film Beginners (original) (raw)

Updated Aug 19, 2022, 8:30 PM EDT

Liam Gaughan is a film and TV writer at Collider. He has been writing film reviews and news coverage for ten years. Between relentlessly adding new titles to his watchlist and attending as many screenings as he can, Liam is always watching new movies and television shows.

In addition to reviewing, writing, and commentating on both new and old releases, Liam has interviewed talent such as Mark Wahlberg, Jesse Plemons, Sam Mendes, Billy Eichner, Dylan O'Brien, Luke Wilson, and B.J. Novak. Liam aims to get his spec scripts produced and currently writes short films and stage plays. He lives in Allentown, PA.

If you're looking to get into the silent era of early cinema, there's no name that is more important than Charlie Chaplin. The comedian, actor, writer, and director is responsible for some of the funniest movies ever made. Chaplin’s real life was riddled with controversies and scandals. He’s a figure that’s both worth celebrating for his achievements in filmmaking and promotion of anti-fascism without lionizing due to his scandalous real life relationships. The Showtime documentary The Real Charlie Chaplin attempted to weigh in on at least some reasons why Chaplin's legacy is so complex.

The 1992 biopic Chaplin starring Robert Downey Jr. covers a good portion of the life of “The Tramp,” but Chaplin’s work is now more readily available than ever thanks to streaming services like HBO Max and Kanopy. Prior to directing features, Chaplin directed many short films. It's fun to watch Chaplin's early work, and reflect on how radically the cinematic art form changed within his lifetime.

Chaplin was able to give himself a proper sendoff. He continued directing until his later year, and created emotional films like Monsieur Verdoux and Limelight that dealt with the consequences of growing older. When Limelight was finally released in 1972, the film won Chaplin a posthumous Academy Award for Best Music, Original Dramatic Score. Limelight explored the musings of an aging comedian, and served as Chaplin's commentary on the way that the film industry had evolved.

It can be overwhelming for film fans interested in exploring Chaplin’s films, as he was extremely prolific. These five films are a great starting point for new Chaplin fans.

The Kid (1921)

Image via First National

Chaplin’s first feature-length film as a director was an early example of his heartfelt nature, and showed how a simple story could be stretched to narrative length. Chaplin had already been successful with his “Little Tramp” persona in short films and early serials, but The Kid developed his madcap stunts into an actual character who goes on an emotional journey. 100 years later, it's still quite touching and entertaining.

Chaplin discovers an abandoned baby through a strange series of circumstances; the infant is left in a pricey car that is stolen, leaving the baby to live amongst poor, working-class folk like the Tramp. The adventure picks up five years later when the boy has now matured into a rambunctious child (Jackie Coogan) who the Tramp must protect from government services that try to separate them.

The Circus (1928)

Image via United Artists

The Circus was among the most ambitious productions of Chaplin’s career, as a studio fire and numerous production delays nearly derailed the production. Capturing circus performers was no easy task, as it required both the usual constraints of a live performance with the wacky mayhem that the Tramp introduced. The Circus was a significant development for Chaplin as a filmmaker on technical merit alone.

However, it was also a more mature film emotionally that introduced a bit of self-awareness about stage performers that is surprisingly melancholy. The Tramp is mistaken for a real thief and pursued by the police, eventually earning a job at a run down circus. Although he desperately seeks the approval of the ringmaster, The Tramp is only unintentionally funny.

City Lights (1931)

Image via United Artists

Although Chaplin’s later films would explore more mature themes and develop more complex storylines, City Lights is perhaps his most gorgeously constructed work. It came at a critical period where Chaplin’s profession itself was in question; four years earlier, the success of 1927’s The Jazz Singer signified that the silent film era may be over. City Lights was an act of defiance that drew acclaim that inspired generations of other great filmmakers, including Orson Welles, Stanley Kubrick, Andrei Tarkovsky, and Damien Chazelle. Chazelle is continuing his homage to Chaplin with his next feature film, Babylon. Tobey Maguire was reportedly cast as Chaplin in the Old Hollywood-era film.

Chaplin proved once again that even the simplest of premises could be stretched to feature length, as the Tramp’s mayhem introduced more than a few detours. In City Lights he’s hopelessly smitten with a blind girl (who he comically adorns with flowers), and becomes roped into the indulgences of an eccentric billionaire. It's Chaplin’s most romantic film; the closing scene is one of the defining pieces of pure movie magic.

Modern Times (1936)

Modern Times was a breakthrough in many ways for Chaplin, as it was both the last time he ever portrayed the Tramp and the first of his films to incorporate audio dialogue (albeit briefly). It also responded to current events with a critical perspective, as the Tramp became overwhelmed amidst the oppressive industrialization working conditions. All it takes is one “kink in the system” to create chaos, a role Chaplin was all too eager to provide.

Modern Times is a great time capsule for the Great Depression, and as a work of filmmaking it features the most tactile and ambitious stunt work of Chaplin’s entire filmography. The mechanical, rotary labor facilities were brilliantly synchronized with Chaplin’s gorgeous score, and the chaos the Tramp introduced stood out even more amidst the automated environment. Still, the film is wrapped up within a heartfelt narrative as the Tramp woos the orphan girl Ellen (Paulette Goddard); it was this emotional quality that distinguishes Chaplin from other silent film stars like Harold Lloyd and Buster Keaton.

The Great Dictator (1940)

The Great Dictator is perhaps Chaplin’s most distinctive masterpiece, as it's hard to overstate how brave it was to develop a parodical version of Adolf Hitler before the United States had even entered World War II. While films like The Mortal Storm and Casablanca were released around the same time and directly incorporated the Nazi threat, Chaplin’s unique blend of comedy was just as impactful. The simplest image of Chaplin playing around with a bouncing globe conveyed the danger of leaving too much power in one ruler’s hands.

Chaplin dual roles expertly. He set aside the Tramp persona for a role as an unnamed Jewish barber, who just so happens to be identical to Adenoid Hynkel, the fascist dictator of the fictional nation of Tomonia. The barber naturally is able to disguise himself as the ruthless leader in order to escape persecution, and while his misadventures managing a war effort feature just as many visual gags as his earlier work, they came as a grim prophecy of world events. Chaplin’s closing monologue in particularwas both a courageous political statement and proof that he was just as impactful with a voice.

The Great Dictator has continued to serve as an inspirational work of satire for modern filmmakers. Writer/director Taika Waititi cited Chaplin's masterpiece as one of the chief inspirations for his satiric World War II film Jojo Rabbit. Similar to Chaplin, Waititi made the bold choice to take on the role of the fearsome dictator for himself. The fact that Jojo Rabbit was surrounded with so much controversy due to its comedic take on fascism just goes to show how much of a breakthrough The Great Dictator continues to be. It's not easy to construct a film that is equally hilarious and insightful, but Chaplin pulled it off.