On my 10th birthday I convinced my dad to buy me a PS2 soon after launch and my first game was a PS1 game by the name of Street Sk8er 2. When I cracked that bad boy open, it was the stuff... You could perform crazy stunts, create custom parks, and it had a killer track list (At least, it was cool as I'm nostalgically recalling it). As a 10-year-old, I thought it was the best game ever, even compared to Tony Hawk games. Being much older than 10 now, I can't say I've played many other skateboarding games since Tony Hawk's Underground and I don't think I ever will. But I would bust open Street Sk8er 2 in a heartbeat.
As an added bonus, my twin sister got Mary Kate & Ashley's Magical Mystery Mall on PS1 for our birthday and I don't know anyone who played that thing.