cdparanoia, then later abcde, which uses cdparanoia.
kazriko
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Desqview, swapping between GoldEd and the BBS watching the users playing LoRD and other games. And before that, scrambling to quit my game and get the BBS back up when I was using my 286 for gaming instead of leaving the BBS running.
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Those terrible, terrible CGA games that I played because for a couple years, I only had CGA and no EGA. The high pitched whine of the CGA monitor whenever I stood behind it.
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When I finally got OS/2, and could play Descent or Doom, while the BBS was handling a phone call in the background.
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Even older, printing out yet another Bill the Cat on my dot matrix printer.
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Typing in games from Compute Magazine into my Atari 130xe, but the checksum being wrong because I used abbreviated basic commands due to being a lazy typist.
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Getting killed by that darn Terminator in Zone 2 of LOD again...
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Going to my Uncle's house to transfer all of Kings Quest 6 from 1.44mb to 1.2mb floppies.
(As for encoding, I used bladeenc originally, then lame, and now oggenc.)