I guess by "older", I mean something between the 1920s-1970s.
Starting up, my personal favorite.

If you're already asking what the heck is going on there, then I've got your attention. I just watched The Sting, and honestly, it was the perfect movie. I loved the pacing, the storyline, the actors, the setting, everything. And I especially loved the surprise ending that seems to pull the greatest con of all: Conning the audience. I won't spoil the ending for anyone who hasn't seen or heard of it, but wow. I thought I knew everything that was coming, but the final five minutes proved me wrong.
Okay, so the movie was filmed in 1973, so it's not quite that old by comparison, but it's set in the 1930s, so it still had something of an older feeling to it. If you love heist movies, I really think you're gonna love this one.
Also, Paul Newman is a sly, cocky bastard and I love it.

Yes, I had an old man crush on him the entire movie and I frankly don't care. It's Paul freakin' Newman and I will buy as many bottles of his salad dressing as I please.
Another really old film I like is a silent film about a utopian, and in some other ways, dystopian, future called Metropolis. Not so much a fan of the pacing in this one, but honestly, it doesn't bother me that much. The sets. Holy crap, the sets. I know through a modern lens, some will sneer at some of the cheesy effects or the artificial atmospheres, but for something like this to come out in the 1920s, the depictions of this futuristic world are astonishing. It just boggles my mind how the sets were all made by hand in some scenes.

Somebody in the 1920s had to build that thing to scale and make it shoot out smoke. And that's awesome.
And, of course, this scene was pretty cool and risque for the times.

It's okay. She's an android.
Anyway, enough of my blather. What kinds of older films and actors do you find cool?
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well my mom had me watching some old Steve McQueen movies with her. and those are pretty cool. not sure which ones we saw though.
The greatest movie known to man kind. Faster, Pussycat! Kill! Kill! :-D
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The Sting is a great movie!
An old actor that I like is Sean Connery! :)

He could talk to me all day about nothing in particular and I would be ok with that. ;)
I would have to say hands down, my favorite is Casablanca. It's an utter classic and it's so beautiful. Not to mention Humphrey Bogart was a pretty handsome man.
I will forever love Anthony Perkins and Barbra Streisand. Any movie with either one of them is amazing.
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