This movie isn't quite in the podcast's wheelhouse, but I think it's worthy of a look.
For Richer or Poorer is a 1997 comedy starring Tim Allen (who was still starring on Home Improvement) and Kirstie Alley. It's a fish out of water movie, where two high powered New York business people hide out from the IRS in Amish country.
The movie is a mess, both conceptually and in terms of execution.