Thanks for the info on what a Walking Boss is. On the "ball the jack" question, it's funny -- the context of the phrase in the song "Walking Boss" seems to suggest a work activity rather than a recreational one--maybe "ball the jack" is a sexual act so named because it in some way resembles something railroad workers did?

Here's the context in "Walking Boss" (with repetition omitted)

I asked that boss For a job He said "Son, what can you do?"

I can ball a jack I can line a track I can pick and shovel, too.

Any further suggestions for sources?