This is certainly a tough one, I started off with OD&D but missed most of the fun bits, races as class especially. I spent most of my youth playing AD&D and has a fun romp of campaigns but I felt the rules were rather restrictive, although I was one player that didn't mind tithing.
My first time behind the screen was Third edition and a few variants along the way. I've run and played in copious amounts of 3.X and while I loved it when it first came out the inadequacies and flaws are so transparent by this point that I find it particularly hard to run or even play in; this includes Pathfinder which does an admirable job plugging a number of these holes but can't do away with what I find burdensome without removing the core of the game itself. I've tried 4th edition in a few games, one all the way from 1-30, and its nice once but I have no desire to play it again. That said if given the choice I'll take a retroclone any day of the week, my preferred game is Labyrinth Lord which closely emulates Holmes Basic, or the Blue Books. Plenty of OD&D with a touch of modern gaming, although since I've gotten rid of ability modifiers that has become window dressing in my Labryinth Lord game.
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