I am an old school gamer, I started in 1979 with a copy of the Holmes Basic set (Blue Book) and the AD&D Monster Manual. I kicked my gaming into high gear the next year though with the Moldvay Basic.
I learned from guys that learned from their older brothers. I played with a guy that had learned how to play from Gary himself using the White Box.
I am certain I am not a 1st Gen. Those are the luminaries of our hobby. The 2nd Gen either learned at their feet as Plato did from Socrates. OR are they all part of the 1st generation? I guess I must be the 2nd generation removed from the source.
I know plenty of "old school" players that were not even alive when even the first Red Box was out. I know plenty of just plain "old" players that love the newest games. So age is not the issue I think.
Where are you? Can you trace your gaming lineage back to one of the Old Great Masters? Should that even matter?
ETA: Cyclopeatron has a nice list of the Generation of Gamers.