Finally got a stick and reved up WC 1 with no luck. Looking through the forum it seems I need a program similar to 'Joy2Key' to get a stick working, is this correct? The answers I found were a little vague for an idiot like myself. :P

What "stick" did you get? WC 1 supports joysticks natively. Perhaps you just need to enable it?

Hey Gydion.
Here is the Amazon page.
It's hooked up to the PC just fine, installed itself and it calibrated, but I don't know if that means I have to do something with the game itself.

http://www.amazon.com/gp/product/B00006B84V/ref=oh_details_o02_s00_i00?ie=UTF8&psc=1

Do you still have your gamepad plugged in? Make sure the joystick is set as the preferred device in windows before starting the game.

It's a common issue with multiple devices. Report back when you get a chance to try it.

Yes, DOSBOX is a bit clunky when it comes to multiple pad/joystick connected, especially if you want to use one for some games and a different one for others.

You can work around that a bit with the integrated mapping tool (CTRL+F1) or some external tools like JoyToKey, as suggested... speaking of WC1 in particular, i highly recommend this in any case, since i've always found the native joystick controls a bit odd (like the "double pushing" a button and stuff)