I used to. I think I started fruit-booting in maybe 1994 and probably stopped sometime in 1998 when college and drinking beer became more important to me. This topic comes up every once in a while. Somewhere I have a VHS tape of us skating back in the day I should find that and try to digitize it for the lolz. I also have some photos from the mid-1990s, somewhere, too.
I was pretty good at real street features, handrails, and even spins up to 7s, but never did any comps or anything because I never liked vert (even "street" courses are/were mostly tranny features).