How can I use Plex Pass to give 2 or more users access to one copy of the same movie?

Does Plex Pass with user support allow selecting each movie you want for every user ?

No.

You can select which library to share with each user. You cannot select on a per-movie/TV show/video/etc basis.

Does not matter if you have a Plex Pass or not.

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as per Ford‘s statement.
You don’t need a Plex Pass for basic sharing.
https://support.plex.tv/articles/204226753-friends
https://support.plex.tv/articles/201105738-creating-and-managing-server-shares/

With a Plex Pass you can further fine tune your friends‘ level of access.
You should be able to restrict the shared library e.g. based on a „label“ you can freely assign to one or more movies within that library (movie: edit > sharing > labels)
image

https://support.plex.tv/articles/204232573-restricting-the-shares/

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