At one point, one of the biggest stars in the whole wide world, silent film’s iconic Little Tramp, Charlie Chaplin, soon became such a big draw that he directed everything he did, which included dozens of short films and eleven features. His attention to detail and penchant for perfection became so notorious that he would take years to make movies, and even got overtaken by the advent of talkies in one famous instance. But, his films are some of the best-plotted, most touching, funniest, and most well-remembered of any comedies of the 1920s-1950s. He was a true auteur in every sense of the word and co-founded United Artists as a respite from the studio system. Golly, he was great. Here are my top 5 of his films.

The Kid (1921)
Chaplin’s first feature as a director also happens to be one of his best and his saddest. A complete ode to 1920s poverty, Chaplin’s Tramp character lives in a shack, eats garbage, and generally hasn’t a care in the world, until he begrudgingly decides to take care of a baby abandoned by its rich mother in the back of an expensive car. The Tramp names the child “John” and for the next five years, he raises him, and eventually making the kid an integral part of his grifting. But, soon child services get wind of a kid being raised by a tramp and they come to take him to an orphanage. The rest of the movie is the two trying to be together in happy squalor and the Man not allowing it. It’s heartbreaking and good.

The Great Dictator (1940)
A startlingly political film made at a time when Chaplin’s adopted homeland of the U.S. was still not at war with Nazi Germany, Chaplin’s first full-fledged talkie was also a huge condemnation of Adolf Hitler, Mussolini, Fascism, antisemitism, and the Nazi party as a whole. It was also Chaplin’s most financially successful film. Chaplin used the world noticing that his Tramp character’s specific mustache bore more than a slight resemblance to the charismatic German chancellor, as well as his own perceived Judaism (he wasn’t Jewish) and decided to play that up for both laughs and poignancy. He plays dual roles, as the frothing dictator Adenoid Hynkel of the fictional European country of Tomainia, and as his doppelgänger, a humble Jewish barber who once saved the life of a now-high-ranking official in the dictator’s regime. Through a series of mix-ups, the barber finds himself in a place dressed as Hynkel and made to give a speech. That speech is possibly one of the greatest monologues of all time, especially for a man known for saying nothing onscreen at all. This is the movie Rogen and Franco only wished they’d tried to emulate back in December.

3) The Gold Rush (1925)
I love this one because it’s possibly the one of Chaplin’s movies that makes me laugh most unabashedly and sustained. It’s got some of the comedian’s most beloved bits and silliest moments. It involves the Little Tramp as a prospector in the harsh winter of the Klondike during the eponymous time when men tried to strike it rich. He lives in a tiny shack on the top of a precipice which eventually starts to fall off during a horrible windstorm. Chaplin was one of the silent era’s funniest and most versatile physical comedians, and while he was never as acrobatic as Buster Keaton or Harold Lloyd, he sure knew how to sell a gag. His famous dance with the rolls was so popular at the time that audiences would demand projectionists stop the film to respool and show the minute-long segment again.

2) Modern Times (1936)
A condemnation of Hitler certainly wasn’t Chaplin’s first foray into political and social satire in the guise of his comedies; the film that directly preceded it was an attempt to skewer the industrialized world and comment on The Great Depression, which Chaplin saw as a direct result of machines now putting people out of work. The Little Tramp is a worker in a massive clock-work conveyor belt whatever while being subjected to many of the indignities of modern living. After a series of unfortunate events that get him fired, arrested, released as a hero, and unemployed again, the Tramp meets a young woman (Paulette Goddard who would become Chaplin’s third wife) who is living on the streets and who is trying to incite the workers of the world to go on strike. At one point during the proceedings, the Tramp gets a job as the night watchman of a department store and sneaks the girl in there to get a chance at “the good life.” It’s one of Chaplin’s most impressive sequences in a film full of huge sets and physical humor.

1) City Lights (1931)
This one has always been my favorite Chaplin, and I think it’s because it’s him at his most romantic. It’s also perhaps the film that best encapsulates the spirit of his Tramp character, trying to have what he wants in a world that seems intent on allowing him nothing. He falls in love with a blind flower girl and doesn’t tell her he’s completely destitute, but wants more than anything to get her the surgery that will restore her sight. At the same time, the Tramp becomes friends with a very alcoholic millionaire who gives the beggar anything he wants while he’s loaded, but has no memory of this friendship when he’s sober. Makes for very frustrating plan-making on the part of our hero. This is a movie that never fails to make me smile and it’s one that I can always put on and be completely engrossed in and taken by.

All of these films should be required viewing for fans of comedy, so if you haven’t seen them, you really should remedy that. What’re your favorite Chaplin films? Tell me about them in the comments below!