This one is really hard and I think my brain is overheating due to all the remembering.. I won't put these in any order, just naming 3 is difficult enough.
Indy 500 screenshot
This was my first car game, and propably one of the most played. I didn't get emotional orgasms or adrenaline rushes playing it, but the game was enjoyable and the old-schoolness means free bonus points on my rank.
Network Q RAC Rally screenshot
I didn't play this very much, because I didn't own it, but this was the first ever game that I played with a steering wheel. I remember all those nights @ my friend, when we just played and played into the night and my friends mum almost had to beat me off the wheel and carry outside every night before I realised what time it was.
Gran Turismo, GT2 screenshot
I hadn't played any sims before this, but I was old enough to realise that the driving model was way off that "Real Driving Simulator" it claimed on the box. The graphics and amount of cars were the features that kept me playing more and more.
The games that were close to top3, and a reason why I'm happy remembering them:
Colin McRae Rally 1 & 2 screenshot
The cockpit view and (totally unrealistic) slides. Sense of speed, and the "being there" -feeling.
4D Sports Driver, aka "Stunts" screenshot
The tracks. Different surfaces with different grip level and elevation changes were something awesome back then.
NASCAR 2003 screenshot
Didn't own the game but I borrowed my friend's copy to test single player and loved the physics and sounds.
GPL screenshot
I think this one is familiar enough here
Richard Burns Rally screenshot
I was really hooked into this, really awesome game. But when I started to learn the stages, I lost my interest and never got it back since. The point of rallying is to drive into the 'blind' spots trusting only your co-driver, and that's what the game can't offer anymore. Competing online against each other with less than 1 sec margins is like modern WRC rallies (like 5 short stages driven 3 times each) compared to 80's Group B rallies (thousands of km's to run, consistency owned fast lines).
Rally Trophy screenshot
Really loved the rwd rally cars, but the physics got oldish quite fast and now I randomly play just one stage (Sweden's 6th) with one car (the Lancia factory model).
Rally Sport download here
A Finnish DOS game, played from top view, there were sliding rwd cars and their behaviour was most realistic I ever saw on MS-DOS.. There was night mode etc, and the graphics (like dirt flying from tyres) formed from triangles
edit: just tested it and its still enjoyable today! try it, takes 5 mins of your time..