I still have Freelancer installed
I should probably re-play the story sometime.
NASCAR Legends is my favourite of the pre-NASCAR 4 lineage. Though between track edits, the GN70 mod and the physics editor you can turn NASCAR Racing 2003 season into a fair-to-middling classic NASCAR sim.
GPL...been driving it since the demo that came with the September (I think?) '98 issue of PC Gamer that previewed it. Bought it as soon as it was released - was a hell of a shock coming from the MicroProse Grand Prix sims and even the Papy NASCAR sims at that point! I've almost mastered the Ferrari these days, and I do okay with the other '67 cars except the Brabham (just don't get on with it) and the Lotus (I'm not nearly good enough to drive it!). As for the mods, hurling the '65 cars around Spa where you're spending nearly the whole lap with the throttle wide open is absolutely joyous. Those '65 cars with the skinnier tyres and smaller engines drive really well in the GPL engine IMO.