Disclaimer: I hate Hollywood-centrism when talking about films so my list pushes international cinema throughout time pretty hard.
If I were designing a film studies 101 class, my shortlist, in no particular order, would probably be:
La Grande Illusion directed by Jean Renoir, 1937. Amazing French, black and white sound film, about prisoners of war in WWI made only 18 years later.
All About Eve directed by Joseph L. Mankiewicz, 1950. Excellent “talkie” with an outrageously witty script plus a very interesting scene with a very young Marilyn Monroe.
Metropolis directed by Fritz Lang, 1927. Probably my go-to silent film choice (and trust me, you really owe it to yourself to watch some silent films). Amazing sets, very interesting sequences, and a really valuable insight into early 1900’s sci-fi.
Ikiru directed by Akira Kurosawa, 1952. Honestly hard to narrow down just one film of his to show and this pick is definitely a personal preference. A great showing of Kurosawa’s craft, but this one specifically has a story with serious resonance with contemporary issues.
Rome, Open City directed by Roberto Rossellini, 1945. Incredible movie about life in Fascist Italy in 1944, finished literally in the same year WW2 ended. A half step between being a conventional film and a “Neorealist” film, where direction and casting aims for realism over drama (e.g. people who really are something are cast to represent those people in the film,a preference for casting people who have no training in acting, using lower quality film stock that resembles news or documentary footage more than looking like a movie).
Tokyo Story directed by Yazujirou Ozu, 1953. Painfully human story about generational divides, urban-suburban-rural divides, and family. Accompanied with Kurosawa, really helps paint a picture of the foundation of Japanese cinema, and honestly, a lot of cinema all over the world.
Singin’ in the Rain directed by Gene Kelly and Stanley Donen, 1952. A musical about the film celebrity world and the transition from silent films to sound films. It’s kind of “bad” to recommend without a reference for all the musicals it is referencing and nodding to but I think it stands up and is a lot of fun even without a background in other musicals before it.
The General directed by Clyde Bruckman and Buster Keaton, 1926. Silent comedy film about a reluctant hero of the American Civil War, featuring TRAIN CHASES. It’s hilarious and a great entry point into silent comedy.
Modern Times directed by Charlie Chaplin, 1936. Feels a bit gratuitous to have 2 silent comedies, but this is just so good, and has so much “industrial prole of late capitalism feels” that’s honestly just getting more and more relateable. Now that I think of it, The Great Dictator is awfully relevant nowadays too
Shadow of a Doubt directed by Alfred Hitchcock, 1943. Hitchcock doesn’t really need introduction, and his whole catalogue is really rich. I pull this one just because the villain in this one is SOOOOOO monstrous and hateable.
The Maltese Falcon directed by John Huston, 1941. Noir films are really intense, and here’s arguably where it starts. With this movie, you kind of have the rosetta stone for reflecting on everything else noir or pulling inspiration from noir.
Blade Runner directed by Ridley Scott, 1982. Helps understand why neon lights are just so damn cool.
Alien directed by Ridley Scott, 1979. I’m not really a horror buff, even if I enjoy suspense a lot. Alien’s got hella suspense and it is just such a triumph of relatively recent, analog special effects and costuming.
Un Chien Andalou directed by Salvador Dali, 1929. I just like making people watch this to have a point of reference that like… yo… art can be real weird and that’s awesome. And it’s only 21 minutes so it PROBABLY won’t bore you to death.
Mulholland Dr directed by David Lynch, 2001. Great way to follow up on Un Chien Andalou, to show how the fruits of surrealism can be made entertaining and appetizing to the larger public. Lynch’s whole catalogue is great in general.
The Killer directed by John Woo, 1989. John Woo’s Chinese-language catalogue is generally really great. The Killer’s probably the one of those most accessible in English. Great look at HK Cinema at its height and for reflecting its end getting swallowed up by the PRC. Lots of fun.
The God of Cookery directed by Stephen Chow, 1996. Kind of a personal pick, but great showing of the comedy half of HK Cinema in its hey day. Content Warning though, has a male actor crossdressing = ugly girl gag. Sigh, 90’s.
Some Like It Hot directed by Billy Wilder, 1959. CW men in drag. Ridiculously funny romantic sex comedy about a couple of guys joining an all women music troupe to hide from the mafia. Really great performances by Marilyn Monroe in this one. Good point of reference for how being horny and comedy have had a long history together.
Do the Right Thing directed by Spike Lee, 1989. Black film is so, so important and I must admit I haven’t watched nearly enough. There are some ummmm things about contemporary Spike Lee, but Do the Right Thing is fucking fire.
Star Wars: Episode V: The Empire Strikes Back directed by Irvin Kershner, 1980. Pretty much THE example of how extremely talented creators can turn a forgettable story into something great. Also the example for how Lucas sucks and how the best SW film had like, no input from him, lol.
Aguirre, the Wrath of God directed by Werner Herzog, 1972. Herzog’s better known for his documentaries, but in this he applies his incredible acumen for doing filming on-location to make this intense movie starring an awful, awful Spanish conquistador.
Bonnie and Clyde directed by Arthur Penn, 1967. The titular characters are awful but also great, and their ending is ignoble and intense. This movie really pushed the boundaries for what was acceptable in hollywood when it came out and even now, to me, feels grimy in a very special way.
Battleship Potemkin directed by Sergei Eisenstein, 1927. Soviet film was super interesting because there was an intense interest in applying Marxist thought to the artform of film. “Montage”, the film technique inspired by Hegellian dialectics, is used in a very elemental, basic way in this film. But the impact is intense and really, we could all be a bit more communist. Soviet art in general is incredibly interesting and here is a vector for approaching it within film.
Reservoir Dogs directed by Quentin Tarantino, 1992. Ah, Tarantino, the movie nerd that makes movies. His movies are always dynamic and fun, and this one in particular has a scene about tipping that’s just timeless. At least, if you live somewhere with tipping.
Citizen Kane directed by Orson Welles, 1941. Citizen Kane is an absolute meme but god, it rules. Not only is it incredibly entertaining, with a sharp script and precise cinematography, but it really is a very broad catalogue of many filming styles and techniques at the time, and effortlessly weaves them all together in a single movie. The breakfast scene is unforgettable.