Judy Berlin

Kind of a double love story. The Judy from the title is leaving for Hollywood. On her final day, she bumps into an old schoolmate, recently back from Hollywood where he apparently was a director, but is now disillusioned and trying to find himself. They spend the day together. Meanwhile, her mother, a teacher, is busy hitting it off with his dad, the principal, who is still very much married to his mother. Of course there are the usual small-town weirdos to spice things up too...
Note that this film is in black and white.