For sure the late 90s Midway games are probably my favorites. Arcade style is best.
Cruis'n, Rush, and Top Gear series, Beetle Adventure, Stunt Racer, Wipeout, and then there were others like Test Drive, Sega Rally, Ridge Racer, Road Rash, Xtreme G. Just so many good ones.
Second to that, the early 90s had a lot of great racers too, like the Off Road series, Mario Kart (and it's many clones), F-Zero, Top Gear, Outrun, Rock N Roll Racing, etc.
I did enjoy some of the early 2000s games like the Underground NFS era, Midnight Club, and Project Gotham were all pretty okay. The era of the racing sim, is what did me in.