For me the worst time on a computer was back when I was using Windows '98 in you guessed it, 1998 all the way until XP came out. The amount of times I had the blue screen of death is uncountable but that wasn't the worst problem I had.
One day the computer was infected by a virus that wiped every JPEG and MP3 file clean. Most of the MP3s could be fixed but the JPEG files couldn't. Each one had just become a white empty space. This really made me mad as I had "visited" a local abandoned amusement park just after a typhoon had hit and took 100's of very good pictures (for 1998 digital camera standards). It was like a digital museum. All of those pictures were gone as is the amusement park. Now a very large hospital stands were the amusement park once stood.
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