Name the Director

George Kaczender?

No

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Looks like Helen Shaver in the bottom shot...that's all I've got.

Ditto.

Shaver’s love interest in the movie photo won an Oscar for his rôle.

Doesn't help me.

Über-famous American director.

Can we get another shot from each of the movies? Or better hints?

The only thing that rings a bell for me, going by that clue, is The Color of Money. (Paul Newman won the Oscar doe his performance)
So I’m going with Martin Scorsese.
Even though I literally don’t know what the first two films could be.

I think you're right because the first image looks like the main actress from Who's That Knocking At My Door, his debut. I watched it the other day see

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I thought the same but couldn’t be sure since it’s been so long since I’ve seen it.

I'm pretty sure it's Martin Scorsese too...Claire's excellent clue cleared itup.

⬆️ Sure is. Middle image is Alice Doesn’t Live Here Anymore.

All movies I have seen but it has been quite awhile. Need to fix that. Ok, will have something up shortly

Here we go. Might be pretty easy.
Edit: I think I made some mistake trying to upload the screen shots 😑

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The pictures are a bit dark, but I think they might all be from Spielberg movies. (E.T., CE3K, and Jaws)

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They are indeed. They’re various night shots from the movies

Next:

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Robert wise?

Correct.

Star Trek: The Motion Picture (1979)
The Day the Earth Stood Still (1951)
West Side Story (1961)