Jimmy Stewart

Bourgeois Nerd

The writer around the corner
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What about The Shop Around the Corner with Margaret Sullavan? She was an early supporter of his and it's rumored that he was in love with her. It's a terrific movie.
 

Dommo

On Mac's double secret probation.
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Anatomy of a Murder for the win!

That has to be one of the first movies where people are actually like REAL people. In that they talk like real folks(as opposed to the cleaned up hollywood idealizations of the 50's), and behave like real people.

I do agree though with the other movies that many of you've listed, as they're all excellent.