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Some old Apple machine my school had with a 3 x 5 floppy disk drive and a green screen that we played Oregon Trail on. Looked like the computers from Fallout 3 and New Vegas. The first computer I actually owned was a Windows 95 machine. It ran like s*** and only had 4GB of memory and 64MB of RAM.
Don't remember the first. The oldest I remember though was a VERY old Mac OS. Old enough to the point of lacking color display. It was either that or a Mac OS that had a blue denim background. Both pre-1995.
Sanity. The most important, yet most lacking, thing in the world these days. Try sanity today! Accept no substitutes!