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My feeling is that the "old school" is something that progresses with time like anything else in the world.
Classic rock is another example. When I was growing up, on the "oldies" stations, all I would hear was stuff from the 50s and 60s, basically. Elvis Presley, Beach Boys, Jefferson Airplane, The Doors, etc. Now, 20 years later, that stuff is all still on the "classic rock" stations but so is stuff like Van Halen, The Clash, Rush, and I've even heard Guns N' Roses and Nirvana on classic rock stations.
I guess to be considered "old school" your style of music has to come and go, and be gone for some time. The Run DMC/Grandmaster Flash old school style gave way to gangsta rap, which gave way to the more materialistic mainstream rap we see nowadays. "Old school" isn't really a defined genre, it changes with the time and trends in music.
It really depends on how you look at it though. If you were to clearly define "old school" or "classic rock," you'd have to look at the initial artists, that first sort of "era" of the genre. Your Afrika Bambaataa's, Run DMC's, Public Enemy, etc.
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