I would have to say THE GORILLA is the oldest I have seen (1939 26 May) I have seen 3 movies from 1939 and that one is the closet to 1 Jan....
The Bride of Frankenstein (1935) The Adventures of Robin hood (1938) With Errol Flynn, Olivia de Havilland, Basil Rathbone, Claude Rains The Wizard of Oz (1939) Gone with the Wind (1939)
Seen some silent movies, not sure about the dates. I have to say that Charlie Chaplin really was a comedic genius everyone credits him to be.
All quiet on the Western Front..1930. Later read the book in college by Erich Remarque that was the basis for the movie.
As a kid I saw a silent movie where a man's car breaks down on a hill. He then starts pushing it and it comes behind another car and that one gets push too and into another and so on at the top of the hill is a cliff and each car goes over one by one.
The Cabinet of Dr Caligari (1920)!! I LOVE 1920s-30s European horror (Caligari, The Phantom Carriage, Nosferatu, Vampyr, etc). Really artistic mind trippy stuff. Horror kinda took a turn soon thereafter, and today's shock/splatter flicks are nothing like the classics. But silent horror is almost like visiting an art museum. PS Technically the oldest I've seen is probably Alice in Wonderland (1903) but it's only 9 mins long so we won't count that.
Gone with the wind. I saw it as a child and felt the ending left a lot of unresolved questions until I realized it was intermittent
Dozens of 'Silent' movies, - 'The General' starring Buster Keaton, and 'Modern Times' starring my namesake - Charlie Chaplin.
99% of the movies I watch were made before my birth, and the oldest I remember is the silent movie, "Shoes" (1915).. I prefer talkies, though.
Definitely something from the 1900s or 1910s decades. I recall seeing the first russian film. I was doing whippets because it existed back then so maybe somewhere someone was experiencing these films with nitrous. Pollyanna was a good silent film