Live was probably in the early 90's at a friend's house with a small group of friends. I think it was 5 Card Draw or some variant of it, where there was a wild card so there was potential for 5 of a kind. We just played for nickels, dimes and quarters, nothing big.
Online was probably just after Moneymaker, when the NHL Strike happened. I played on so many different rooms, many I don't even remember anymore, but the big two were Full Tilt and PokerStars. It's too bad that Full Tilt was run so poorly, because the best tournaments and games were always on there, and watching Poker After Dark, it was the heyday for online poker. Of course, Black Friday changed all that.