If you loved Milk Money, try The Pentagon Wars
A bridge between a film you've already seen and one most people haven't. The Pentagon Wars has roughly 3.8× fewer votes than Milk Money — it's a deeper cut, not a mainstream recommendation. 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 sit in Comedy / Drama territory. If that's the register that drew you to Milk Money, the second film will land in a comparable space — through a different lens.
What The Pentagon Wars is
Apparently someone made a war movie that is funny. The BFV is a very expensive military project. It somehow took 17 years to make a vehicle that did not work.

