Start with a kind of story
You do not have to know film history to enjoy an older movie. Pick a premise that interests you: suspicion in Rear Window, a complicated relationship in The Apartment, or an unfamiliar city in The Third Man. The classic collection offers a shorter starting list than the full catalogue.
Read the running time before deciding. Seven Samurai and Lawrence of Arabia need a different amount of space in the evening from a more compact drama. Saving a long film for another day is not a judgement on it. It is a way to give that film the attention you want to bring.
Use the original year to identify the film
A restoration can be recent while the production itself is decades old. Check the title and original year, then read the edition details at the viewing destination. A different image, subtitle track or restored sound mix does not necessarily mean you found a remake.
The year index is useful if you want to explore a particular period. Try one film from a decade you rarely watch, then follow the genre or cast links if it leaves you curious. There is no required sequence.
Choose the edition for your screen
Check aspect ratio, captions and available audio where the viewing service provides those details. Black-and-white photography or an older recording does not require you to use uncomfortable picture or sound settings. Find a clear, stable edition, settle the controls and let the film make its own impression.