"Damn Skippy" is an older version of "Fuckin A" or "Word." It is usually a reply to a concise statement summarizing a troublesome situation.
as in, "This fire is gonna spread and we need a plan." 'Damn skippy we do.'
(appropriate reply: damn skippy, fuckin a, word, you KNOW it.)
a person under the age of eleven or shorter than five foot four that is a complete douche.
my ten year old brother is a douche skippy
When you hit a guy with a rock, and bite his ear off.
I just skippy John Joe'd my dad.