It's far from the oldest, but The Rocky Horror Picture Show (1975) deserves mention for still regularly being shown in movie theatres, over 50 years after its original release.
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Buster Keaton films still have their waves of popularity.
Just about anything in The Criterion Collection might qualify.
Here's a convenient list, starting with The Pillar of Fire (1899):
https://letterboxd.com/davidblakeslee/list/the-complete-criterion-chronology-1/
Duck Soup, Horse Feathers, Go West
“Wizard of Oz” and “Ten Commandments” are shown on TV regularly in the United States. They are kind of a holiday movie tradition.
Put Ben-hur in there too.
I would imagine the Christmas classics get watched more than anything else. Especially things like It’s A Wonderful Life and Miracle on 34th Street. Compare that to just about anything else and most people probably only revisit other old/b&w movies on the rare special occasion a lot less often than those.
I ❤️ Miracle on 34th St. I can watch that anytime.
I'd put Gone With The Wind (1939) on that list.
There was a surge of interest in Nosferatu (1922) when the re-make came out, and Metropolis (1927) is always popular.
My favorite Lang film is "M" (1931), which benefits from not being a silent movie, but it is in German.
Marx Brothers (1928-1949)? Chaplin? Laurel and Hardy? All classics.
Cocoanuts by the Marx Bros.
I watch The Thin Man every couple of years.
I vote 12 Angry Men.
I miss the dollar movie theaters. Some were even cheaper. Nothing new, just playing classics. Usually the popcorn was much cheaper as well. They closed down though...
The original Bedazzled was quite a treat. Or the original Secret Life of Walter Mitty, Grapes of Wrath. Etc..
Mary Poppins, sound of music, chitty chitty bang bang.
The ones that come to mind are probably the old monster movies like Dracula and Frankenstein or some of the early Three Stooges movies. But even then, they are likely not watched en masse except by lovers of genre pieces.
Wizard of Oz
Steamboat Willie 1928?
i think that criterion's streaming channel might have pushed that date ... the 1930s ... back a little early but not by much. They have silent movies and sell silent movies on disc. So there is some small market for it. film is an interesting art form as it is barely older than the oldest human being alive today