Moose
I was introduced to the Talking Moose when I was 16 or 17, putting it right around 1990 or 1991. I loved it and loathed it. The damned thing would interrupt you when you least wanted it but teaching it how to swear more than made up for it’s shortcomings. I only mention the Moose because I was thinking about it. It’s still around, still as annoying as ever and still as lovable, you can find it here. Mac only. The longevity of this thing amazes me.