Your turn.
Largely the same story. Yahoo!, FICS, and the chessmaster program.
The only Chessmaster program I had was CM2000, a DOS program with absolutely no personality. It did, however, come with a huge database of 100 games.
For a time I had a program called Power Chess. This featured the Chess Queen. The Queen would talk to you -I think as little or a much as you allowed- explaining moves and telling you why you lost. It was voiced by voice actress Natacha LaFerriere. She had the most soothing and appealing voice. You can hear her here.
I joined ICC in 1989 and it became pretty much a nightly haunt for me.
Since ICC didn't exist until 1995, can I assume you meant to type 1998 0r 1999?
I used to play every morning after work...sometimes at ICC as a guest but mostly at FICS.
Here's a 1990 ad for the Novag board with the auto-sensory feature:
Oh, I remember having some device like that.
I remember when you made a bad move (like giving up your queen for nothing) the computer voice would say:
"Are you a salesman? Because only a salesman would make a dumb move like that."
Which I thought was really weird thing to have it say heh.