Midtown Madness 2.
I only had a handful of games growing up and MM2 was my favorite! I'd would drive through the cities for hours doing whatever. I did every race, I knew the game inside and out. I even had a steering wheel and pedals for it.
Eventually I discovered modding and that sparked my interest in computers and made me love the game even more.
It took until 07 when I finally convinced my parents to get me a console. I had been playing a game from 2001 for 6 years, I was shocked seeing the graphics difference.
Other notable favorites:
NFS Hot Pursuit 2
Combat Flight Simulator 3
Zoo Tycoon 2
Crashday
18 Wheels of Steel: Pedal to the Metal
I LOVED Black and White!! I completely forgot about that game. They really do need to make a new one. At least remaster it.