I usually enjoy instrumental/virtuoso music when I find it, so jazz was an obvious genre for me to explore... but I knew absolutely nothing about it till about a year and a half ago. (Unless you count Flecktones as jazz?) At that point I (luckily) ventured into jazz with a copy of Kind of Blue that I randomly picked up at a flea market. It was a great one to start on, easy to listen to, but full of obvious virtuosity. From there I started reading (and then buying) to figure out where this album fit into the grand scheme of jazz history.
I still enjoy Kind of Blue when I'm in the mood, but I've found some other musicians that I listen to a lot more often- Brubeck, Desmond, Rollins & Monk are my favorites at the moment, and I'm looking for some more exposure to Brown/Roach albums.