I played a Need for Speed title in the early 00's though I have no idea which one. I was still new to gaming being a wee lad so I thought the game was broken when I couldn't accelerate. In hindsight, I probably just set the game to manual instead of automatic.
I also played around with Need for Speed World for a bit. I wasn't going to sign up for a subscription though so I was stuck at the base level. I do have fond memories of it though.
The first proper NfS title I played was Undercover and holy, that game almost ruined the series immediately for me. Absolutely awful game, terrible graphics, empty and bland map design and a really weird, hard to follow story.
I didn't touch the series until I played Payback. It was dirt cheap because of the microtransactions so why not buy it. It's not bad, it's pretty good if you can stomach needing to farm vehicle upgrades. Then I played Heat which is awesome, basically everything Payback should've been.
I probably wouldn't have played Most Wanted if I didn't start watching KuruHS. He basically sold me on playing it.