I was listening to the radio (remember that? like TV but without pictures and it comes through the airwaves for free...unless you're one of the schmucks who pays for it) and heard a show where film makers talked about movies they can watch over and over.
I have many of those. Some I own and some I don't. When I do own them it's usually because I got the flick as a gift or from a thrift store. I can't remember the last time I paid full price. There are a few that I check out from the library over and over.
Here are a few favorites:
Escanaba in da Moonlight. Very funny take on hunting camp in the Upper Peninsula of Michigan. I own a thrift store VHS copy that is dying slowly.
Kitchen Stories. A scandanavian film about anthropologists studying the kitchen habits of Norwegian farmers. Very amusing in a slow depressing way. Library checkout...repeated.
Grey Gardens. The ORIGINAL documentary NOT that HBO tripe with Drew Barrymore (who is a fine person as far as I know but that movie should not have been made and adds nothing to the story). Got the DVD set as a gift.
Kinky Boots. Cute story of a shoe factory in England that struggles to stay open and keep its staff employed. I own it. Don't remember if it was a gift or thrift.
My Name Is Joe. The story of a scot getting sober and trying to stay that way against some serious odds.
I bought a VHS off the internets used...it's very hard to find this movie and I love it.
There are more but I'll stop now.