All this talk of Daytona USA just gives me another excuse to post the trailer for the new one:
Hearing that DAAAAYTOOONAAAAAAAAA again made the hairs on the back of my neck stand up man.
Anyway, the first game that came to mind for me when I opened this thread was Screamer 4x4.
Released some time around 2000/2001, this was a game I liked because it ran well on my old laptop with it's VIA Graphics chip I had at the time. Focusing more on realism than anything else, it tried to give you an experience of competitive off road driving using a few popular 4x4s from the era with a range of upgrades for each.
It had a couple of different modes, from shorter stages making up a championship where you were forced to drive a certain route between checkpoints to my favourite, the Pathfinder mode, where checkpoints were set miles apart and you could take whatever route you wanted. Penalties were given for hitting or missing checkpoints, or having to be recovered.
The game gave you control over locking of diffs, low/high range, 2WD/4WD etc. which was pretty much unheard of at the time. It also had relatively realistic damage for the time, with deformable bodies and mechanical damage.
And hey, once you unlocked the lifted 90s Hilux secret car, you were pretty much unstoppable.
I still go back to this game ocassionally now. There have been a couple of good attempts to re-create it since but none of them, for me at least, have done as well to re-create that feeling of barreling over a boggy moor in the pouring rain in an old Land Cruiser with a wonky wheel because you landed a jump badly, with nothing but a compass to guide you to the next checkpoint.
It even had a properly good cockpit view:
Edit: I've gone maximum sad git as well looking at that last picture of the Land Cruiser there, I knew something looked familiar...
Yes, even has the same TM4000 cassette player that's in the Corolla.