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Not sure on the Annie Oakley thing, but maybe I can help out on the deadhead:

My grandfather worked for the Northern Pacific Railway for some 30 years, and he told me at one time that it meant when an employee was being transported from one place to another at the railroad's expense. Generally my grandfather could go anywhere at any time if he had work waiting for him.

The expression was supposed to have come from a combination of "dead weight" and "extra head", so it got shortened into "deadhead". Also known to my grandfather as "riding the cushions." (As opposed to working the train as a trainman.)

Hope this helps.:trink39:
 
Yep! We called it "Bobhopping"!

Ingersoll444:

We used to call running without the trailer "Bobtailing." Running "Bobtail" mean't a very ruff ride and you couldn't wait to get a trailer on for a smoother ride. Any trucker hated "bobtailing" for any distance. I drove various trucks from the late 60's till 1987 when my back gave out. Anyway, "dead heading" for pulling an empty trailer and "bobtailing" for driving the cab only and no trailer is all I have ever heard it called. I really don't know anything else. :fing32:
 
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