Nice guess, but no. After a lot more digging, I finally came up with the answer: "The Great Land of Small" which is apparently a very Canadian film. (It's filmed in Canada and set in Canada with Canadian actors.) This would explain how I got a chance to see it: when I was a child, I used to live in Minnesota. After working with different combinations of key words from my fragmented memories, I turned up this site on it:
http://www.amazon.com/gp/product/6303340911/103-7406944-2200606?v=glance&n=404272It's kid of surprising (I think) that this piece hasn't been made into a DVD yet. Practically everything else has including films that could be used as torture instruments. The mixed reviews I'm seeing so far indicate that for this film, either you love it, or you really, really hate it. I've got a copy on order now, so I'm about to find out what those pleasant memories are worth for myself.
I'll be sure to report back when I do.