My pick: Either Need for Speed Most Wanted (2005) or Forza Horizon 1.
Supertuxkart
Burnout: Revenge on the PS2
Burnout 2 or 3. Because the object is to either crash or cause crashes.
the soundtrack was killer too.
RalliSport Challenge 2
Top Gear 3000, for SNES. Honorable mentions to Mario Kart Wii (because steering the controller to steer the car will never not be fun) and Horizon Chase Turbo (which is pretty much a modern Top Gear game).
I still play a lot of need for speed underground on my ps2.
I’ll also always love Carmageddon 2. So much fun and a soundtrack full of Iron Maiden!
Split/second. You could blow up huge chunks of the track, which than changed the route. You could blow up and airport. And it was made by disney, of all studios. Better action than Burnout imho.
F zero x N64 is the one I had the most fun with
Live For Speed
Still love it, now with mods :)
I think it is a tie between iRacing and Assetto Corsa, tho I personally preferred AC for the graphics and cost.
As for silly fun, Super Off Road on SNES. I could spend hours playing that as a kid. 🛻💨
Need for Speed: Underground 2
This game informed a lot of my early musical tastes and probably contributed to my current tastes in one way or another.
Excite Truck
Stunt Car Racer on the Amiga.
Outrun, for the music
Arcade racing: Burnout Paradise
Sim racing: Assetto Corsa