Willy Santos just because the "best" skater at my middle-school thought he was the absolute coolest pro skater ever.
However, I think Kris Markovich was probably the first skater I found on my own that I was super hyped on (until I met him in person, that was a huge bummer). Or, maybe, I was super hyped on Dan Drehobl first because I remember watching his part in some old Thrasher VHS over and over again.