I can probably trace it back to TV, as a child, I watched every episode of Black Sheep Squadron, and the mechanic was a bad-ass dude with a chewed-up cigar always hangin out of the corner of his mouth. Later I watched a lot of The A-Team, with Hanibal smoking a chuchill or lonsdale whenever a "Plan Came Together".

My first cigar was probably a RyJ "It's a Boy/Girl" thing, but I can't really remember