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I believe the first pole jam was Jeff Hartsel in an ad back around 89. I tried googling it but couldn't find it. It definitely blew my mind at the time.
Chris Cook had a Jimmy'z ad doing a pole jam in 1987. It'll be up on the Thrasher archives in a few weeks.
You're right, I just rediscovered this page after some intense googling:
http://www.50-50.com/absorb/interviews/jef_hartsel.shtml"50-50: First we want to know about the pipe jam. The wallie off the bent pole. Was that a Hartsel original?
Hartsel: Ummm, no. The originator of jamming into and up and off of anything is definitely Chris Cook.
50-50: So it's a Cooksie thing not a Hartsel thing.
Hartsel: It was a Cooksie thing, but that pole just became the main pole for that shit.
50-50: First time I saw it, I thought you were ollieing over it.
Hartsel: Yeah, that's what a lot of people thought."