I used to play Motor City Online a few years back, and I love that type of older, muscle car/hotrod sort of thing. I’ve played a few of the Need for Speed games, but I’m not looking for Ferraris or Lamborghinis…maybe some old 50s, 60s, or 70s iron.
There are a ton of car games around; too many to check out each one. Any recommendations?
not really my territory, but I’d check out the Gran Turismo series for the ps2. It’s bound to have some muscle cars in there.
a quick google search turns up Midnight Club 3 dub edition and Burnout 3 takedown as possibilities as well.
GT is more a realistic racer, MC is all about racing through a city and finding alternate paths and such, and Burnout is more an arcadey sorta thing where you get points for smashing into crap.
Again, though, I’m not a huge racing fan so definitely do more research on these before you do anything rash like buy one based on my advice 
Most games these days have a mix of classic & new. Midnight Club 3, for example. Other games, like GTA3, have a bunch of cars from the '60s to the '80s but without the actual model names. Same for Test Drive: Eve of Destruction, a demolition derby game.
If you like Porches, check out Need for Speed: Porsche Unleashed. Nearly every single Porsche model from the 356 to the Boxster. The 924 is missing from the PC version for some reason but is present in the console version.
Also try one of the older PC titles in the Need for Speed line, there are a bunch of user-made classics for these. For example, Here’s a '71 Riviera, one of 1175 user-made cars for High Stakes.
That reminds me: GT Legends definitely has classic cars.
Gran Tourismo 4 for the PS2. It has literally hundreds of classic cars for you to buy, win and unlock. From an 1888 Daimler 1 cylinder, to Formula 1 cars and everything in between.