Deep Blue versus Kasparov was an pivotal moment for me. At the time I was playing lots of chess on the computer. (And usually losing.) So the prospect the best player in the world cannot beat a computer was a depressing prospect. Maybe it is a sign of how much I had matured (or immatured) to think a computer could beat someone better than me at trivia. Maybe it has something to do with routinely using computers to compile things for me in minutes that would take me days.
If the below video does not play, then try Ken Jennings: Watson, Jeopardy and me, the obsolete know-it-all.