If you loved My Favorite Year, try Milk Money
A bridge between a film you've already seen and one most people haven't. Here's what they share, and what the second one does that the first one doesn't.
What they share
Both films are directed by Richard Benjamin, and they both carry the cozy mood tag, and they sit in Comedy / Drama territory. If that's the register that drew you to My Favorite Year, the second film will land in a comparable space — through a different lens.
cozy
What Milk Money is
Here's a film that makes a lot of questionable choices. Three suburban boys pay a prostitute to disrobe, then she winds up in their town as she flees some mobsters. Soon she's romancing one of the boy's fathers, who is clueless about her line of work. It's a sweet film if you don't think about it.

