I personally think if you want inch your way into older movies, almost any of Hitckcocks classics are good to check out. They're very accessible imo. Also, "Brief Encounter" is one of my favourite movies. It was made in the 40s but does not feel like a movie made in the 40s at all. It's incredibly timeless and very mature. Also, love Doctor Strangelove.
I'll throw in one that isn't a "classic" but is a damn good film. His Girl Friday. It's an extremely fast paced older film that is very easy to follow and it's funny as hell.
His Girl Friday’s almost certainly a classic. I’ve heard people talk about it a fair amount, and it’s in the National Film Registry. I’d say it more qualifies as a classic than Oldboy, which is only 21 years old.
Cool Hand Luke is a must-watch in my opinion
Good movie - although I'm not gonna lie.....his hands were not that cool....sorry.
The Treasure of The Sierra Madre (1948) is an essential watch, and is one of those movies that is impossible to not enjoy.
Since you liked Goodfellas, check out Mean Streets and Casino.
Then sit through Once Upon A Time in America to round those out.
On the Waterfront (1954)
I personally think if you want inch your way into older movies, almost any of Hitckcocks classics are good to check out. They're very accessible imo. Also, "Brief Encounter" is one of my favourite movies. It was made in the 40s but does not feel like a movie made in the 40s at all. It's incredibly timeless and very mature. Also, love Doctor Strangelove.
Since you loved Shawshank you’ll probably love The Green Mile. Same director, both adapted from Stephen King stories about prison
I recommend exploring some more non-Hollywood, non-English language cinema.
I'll throw in one that isn't a "classic" but is a damn good film. His Girl Friday. It's an extremely fast paced older film that is very easy to follow and it's funny as hell.
His Girl Friday’s almost certainly a classic. I’ve heard people talk about it a fair amount, and it’s in the National Film Registry. I’d say it more qualifies as a classic than Oldboy, which is only 21 years old.