Wow this is a tough question. If I had to chose one year in the past to be stuck in I might pick 1984. The music was still good. The economy was good. America was optimistic. But maybe that was because I was a young teenager then and my perspective was influenced by my age. That was the year I got my first computer - a Commodore 64.
I guess I would probably pick the 1950s. As much as I love Old West history, I am not sure I would want to be stuck there. I like modern conveniences too much!