NASCAR Road Racing Trivia (Windows)
The back of the box touts "modest system requirements", and they weren't kidding. NASCAR Road Racing only requires a Pentium 133, without any 3D acceleration. For a game published in 1999, that's pretty impressive coding.
Darrell Waltrip's car in the game is the "#17 50th Anniversary of NASCAR" car from the PRIMESTAR 500 Atlanta from 1998. The only reason that he ran that car was because his sponsor "Speedblock" pulled out before the race.