Ooo, this is kinda my bread and butter. Never easy to pick favorites.. Probably have some classics on here because I think there is some beauty in simplicity and some of the newer games have lost their way.
Gran Turismo 2 (PS1) - Classic GT. In modern times, I find it a perfect balance of arcade and sim. The handling and feel is forgiving by todays standards and allows you to sit back and relax with a controller. Massive selection of cars, a lot that no newer games even bother having. Love the career/gameplay structure here as well.
Gran Turismo Sport (PS4) - The best racing game for online match-making and ease of entry. Very high skill level required when you're near the top and a great rewarding sense of competition. iRacing does exist, but its got a (very) high cost barrier to entry if you really wanna get into it and it is a bit simple/dull in terms of presentation compared to more popular racing games.
Need for Speed: High Stakes (PS1/PC) - Aside from the unique Porsche Unleashed entry maybe, High Stakes is the peak of NFS in my opinion. Another example of something being arcade-y but still giving a sense of playing with cool, real cars. The tier of cars available here are great. The whole vibe, from menu design and a killer soundtrack, is something that Need for Speed has lost and will probably never get back.
Top Gear (SNES) - One of my earliest racing game experiences. Ugh, the music is so damn good. Hard and unforgiving in the way old games are, it's still fun even if you only play the first few levels for a bit. The sequel, Top Gear 2, doesn't quite have the same style or music, but is easier to progress and play as a video game.
Project CARS 2 (PC) - My racing game of choice for VR. I think it's got a great sim handling model and some pretty good visuals. Using VR for racing sims is the way forward and if you're game doesn't support it, then why even bother. Lots of good race cars to choose from, but not a great selection for street cars.
Tokyo Xtreme Racer 3 (PS2) - The quintessential Wangan racing game. It's a crime they have not made a new one. Very unique, not a good or realistic handling model, but you get used to it. Good selection of japanese cars. Decent customization.
Tokyo Xtreme Racer Drift 2 / Kaido Battle: Touge no Densetsu (PS2) - And the quintessential drifting game in my opinion. I originally played the japanese version of this, long before it was available over here, via an installation on my PS2 HDD. Again, kinda unique/bad handling model, but you do get used to it over the dozens of hours of gameplay available here. Unique progression system. Big variety in japanese cars. Decent customization. Again, blasphemous they haven't made a new one.
Colin McRae Rally 2.0 (PS1) - There are a lot of fun rally games. Probably only singling this one out because I bought it in 2019 and played a lot of the career mode. I hadn't played it prior to this and I think it still holds up. Put the time in to get comfortable with the crazy twitch reflexes that a rally game requires and eventually you'll get into the groove and feel so damn good when you nail a course.
Forza Horizon Series (Xbox) - I think this is going to be your best bet for an open-world racing game experience. Nothing else is coming to mind at least. Excellent balance of arcade/sim handling, enough so that cars feel like cars are bound to physics you can relate to but forgiving enough to allow for play on a controller and an easy sense of fun.
Monster Energy Supercross 3 / MXGP PRO - My picks if you're looking for two wheels on dirt. Supercross is indoor/stadium style courses, and MXGP are the larger outdoor courses. Can pick whatever fits your style. I did play Motocross Madness and some others as a kid, but I don't think there is any reason to go back to older games in the dirt bike genre.
F-Zero (SNES) / WipEout XL (PS1) - If you're looking for your futuristic, hover vehicle racers, these are it. One 2D, one 3D. Blindingly fast speeds. Each with a unique style of their own. Each with their own awesome soundtracks.
Tourist Trophy (PS2) - The Gran Turismo of motorcycle games. Obviously, both from Polyphony Digital. And they haven't made another one yet! Ugh, so dumb. Has that special Gran Turismo vibe, with the music and the visuals. Great motorcycle selection.
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