I once went to a lunch (I think it was in 2017) with a bunch of random pros through a friend of mine. Most of these guys were early to mid 90s pros. Most of them were chill. But one that was a total tool was Scott Oster. I was trying to cool guy everyone at the table and it was mad corny.
First cool pro sighting as a kid was when we saw Jason Lee and Mark Gonzales at the Brooklyn Banks when Blind just launched and they were sharing one board and skating the smaller banks.