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I remember having an Iomega Zip100 drive… - I’d be amazed to hear that the shortcut you have on your desktop is to one of those?! Mine died many eons ago 
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I’ll second that @BrokenCanoe. I still have a working Iomega Zip100 drive with several disk, but no longer have a PC with a printer port to hook it to.
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No, but I’ve had several. This is a 2Tb. Not a big difference; I also used the 1 & 2Gb JAZ disks.
Maybe pick up a serial to USB adapter? If they make 'em…
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