one of my craziest ones was on a plane to barcelona a few summers ago. for some reason my friend shawn and i had been talking about how low pat duffy wears his hats--like, over his eyebrows--and had been pointing people out that were wearing hats like that. anyway, we're on the plane and shawn goes, "check it out, pat duffy." i look and it's a guy with a hat pulled low, but i go, "nah, dude his hat's not that low," and shawn goes, "no, i mean, pat duffy," and it was pat duffy sitting next to us. he was a super nice guy, later he helped me get some money converted at the airport, and we ran into him again at forum. but it was random as hell, sitting next to him on the plane.
another personal favorite run-in was the one time i saw bobby puleo. was skating the banks this summer and he cruised in from the top, stalled the spine-quaterpipe thing, then cruised off down the hill and out the other end of the banks, leaving as mysteriously as he came.