Post since my last on NASCAR games.
Dale Jr. is about the one constant from 02 on, and while others I can't list the usual leaders well for most games I can 03-05.
NT03 (PS2): Dale Jarrett, Jr., Mark, Sterling Marlin (remember him?), Bobby Labonte, Tony, Ricky Rudd, Jimmie, Newman, Jeff Gordon, Kevin Harvick, Matt Kenseth. Kurt, Bill, and Michael Waltrip popped in from time to time.
NT04 (PS2): Thinking about it, simply replace Mark with Kurt, then mention Bill and Ward from time to time and you're set.
2005: In general order; Harvick, Jr., Stewart, other big names, everyone else.
Going back to 2004, correct me if I'm wrong, but I seem to keep thinking it had more music tracks than most others.
The worst thing about 08 and 09 was not only the AI being woefully unchallenging, but then the physics were awful. It wasn't a matter of you fighting the AI so much as it was trying to get the damn car around the track. No wonder most of that game's community was involved in setups. Even I, someone who normally didn't mess with anything, had to resort to making some myself.
First clue about 09 on PS2 was that there was a second driving mode. "Easy mode"? "Simple mode"? Whatever it was called, if you decided to turn, even if you were on the outside at Daytona, you went at full lock, and without any resistance.