What's the oldest basketball video game that you still play regularly, or at least on a semi-regular basis?
For a while there earlier this decade, it was NBA Live 06 PC for me. By virtue of playing it for various Wayback Wednesday features, I'd probably say that it's the PC version of NBA Jam Tournament Edition. It still holds up so well, and I feel that I can dust it off anytime I want some retro arcade hoops action.