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My first game was a simple baseball game back around 1980 when i was 10 years old. I remember it was called "Baseball Manager", and all it was was a yellow magazine like booklet with some instructions, a couple of charts, and roster pages for some of the all time great baseball teams. Each player had like 4 ratings (batting, power, speed, defense I think) and you rolled 2 dice and looked up each result. Moved on to Avalon Hill and Strat-O-Matic from there.

I haven't played 2k8 but as a very casual college basketball fan, I found DDSCB 2020 totally addicting. I think it offers enough detail and strategy for a more die-hard basketball fan yet it is very user-friendly for someone like me to get totally into it.