Damned nice thread.
Ok here goes:
My first to play and to own was "Lamborghini", on the SNES, for a 2D game, pretty cool.
During that time I tried the new "box" at a friends house called PlayStation and believe me or not, it was the first time I saw 3D real time graphics

.
(It was already early 1999 at that time, anyways...)
He showed me two racing games, one was HP3 and the other one GT. I was 9 I believe, so I really coudn't do anything with GT, it was so realistic, that it was kinda unplayable to me. The guy I always visited with the PS was 13 back then, much more mature than me and he LOVED GT, I know he turned it on, showed me all the menus and options and I didn't really understood anything and then he left me with the game alone in the room, I was pretty shy as a kid back then so I thought "Hm, why not, give it a try", but the car he gave me had HUUUGE turbo lag, so I thought I kinda broke the car or something, left the controller on the sofa and put on this face:

Then he came in and asked if I didn't like the game and I lied and said yes, although I feared I broke his car, so:
But NFS3 on the other hand made me addicted, I LOVED watching him playing this game, the HP mode. I loved the tracks with all the hilly mountain like scenery and of course the exotic cars, I was amazed, but he was pissed as he didn't really like the game lol.
Then a "real" friend of mine bought also a PS and a "demo1 disc" came with it, on it a demo of GT1. Somehow I learned to really love this game and we only played this demo for hours every day although we already had real games.👍
Besides, in my opinion, this game has the best intro to ANY videogame EVER:
Isn't it amazing even today?
Half a year later or so I bought my own PS with the game I was most addicted to till this day, I played it several hours each day, for pretty much a whole year: NFS4, High Stakes. I adored everything about this game, graphics-physics-scenery-tracks-cars-music and the AWESOME sound this game had at the time. You could for example hear all kinds of animals like cats, dogs, panthers, birds, wolfes, etc, etc., all fitting the track you were driving on, REALLY added to the atmosphere.
Here an example of the amazing music they used back then, much better than today's emo rock and pop.
So from there I started bying a lot of demo discs and I will briefly name the racing games I liked but never bought:
1.ColinMcRea Rally, man, what an amazing game-rented it though.
2.Toca 1, incredible for it's time.
3.Toca 2, sublime in every way.
There were also others, but I do not really remeber them, they were not as good.
So the next racing games I bought for the PS1 were:
1.Driver 2: Stressed the old hardware way too much, great nonetheless. It even had "round" corners in an open world racing game on the PS1, that was something really.
2.Colin2: More or less a perfect rally experience, really good game. (Played through it again a year ago or so for nostalgia's sake lol)
3.Toca World Touring Cars (Toca3): Man this game had EVERYTHING. 12 cars grid, extencive damage, roll-overs, good physics and graphics and sound, GREAT A.I., all of that on a machine with 4MB main memory

, spent a lot of time on that game.
4.Ridge Racer Type 4: Ha, simply perfect graphics for PS1 standards. Much better than GT indeed, and that at double the framerate, I don't know how Namco pulled this of back then, some serious wizardy. Loved the music in this game so much! And the intro first with that chick you know?!

Hey I was 11 or so...

Watched the intro EVERY time when fired up the game and tought "oh yeah baby" when the chick bit her lip in that one scene-at 1:42 it is...



5.And finally GT2: REALLY hooked to this game, so much cars, so much to do! Just an awesome game that was.
And then came the PlaySation 2 with significantly improved hardware and I bought like every gaming magazine, which had an article on GT3.

I bought the bundle, and my first racing wheel with it, the Driving Force EX or something like that.
I was SHOCKED how amazing this game looked on my TV and was simply blowen away by the driving feel with the wheel, was so addicted to this game.
This video shows fairly well how big the graphical leap was:
Other PS2 racing games I bought:
1.WRC2: Great graphics but ****** physics. Still, great atmosphere created in the game with the official licence.
2.Supercar Street Challenge: Totally useless game, but really cool music during the races.
3.Burnout 2:Great arcade fun.
4.NFS HP2: Really really good game with great graphics and sountrack, well and gameplay of course.
5.NFS Underground. Stunning graphics, good arcade fun.
6.Enthusia:Unbelievable physics and good graphics but I didn't like the career mode of this game.
7.Tourist Trophy. Well, GT with bikes=amazing.
8.GT4: Loved it, but not as much as GT3.
Now to the recent gen, the PS3:
1.F1 Championship Edition: Great gameplay (little arcady), great wheel feel, good A.I., imo-amazing gameplay graphics-really clean and it looks amazing during the practice sessions in the morning, here a vid:
And also one I made, with some slick overtaking:
2.GT5, of course: Well, still play it, but imo, the worst GT ever, besides GTPSP.
That's it I guess.👍
(Oh and yeah I love these meme faces pics

)