This has been sitting on the bookshelf in my parents' house since I was a kid, and to this day, I still have no idea what it is or how to play:
It was given to us by my grandma, and the best my dad can remember is that "it's a puzzle of some sort". He claims to have solved it once, but can't recall anything beyond that.
I tried Googling "Ol' George's Nail Wail" to no avail. Here are a couple more pics from other angles: