I still have some nudie pics I downloaded from usenet in the early nineties. You had to download the uuencoded parts , stitch them together in an editor and then undecode them. Then the JPEG viewer took about a minute to display the image on a Windows PC with a 386 processor.

Does 20 years old porn count as vintage porn?

dodgeball.exe, a Shockwave Flash game (from before Flash was bought by Adobe) downloaded from the Cartoon Network website in 1996, where you play as Deedee and throw dodgeballs at Dexter from Dexter’s Lab.

Based on file modification dates, it’s this drunken cow:

It’s from October 2004. Initially I doodled it in my lab notebook; back then I was a Chemistry freshman, and I always doodled my stuff like this. Then I redid it in a computer.

(Her name is Vaquetila. Vaca = cow, etila = ethyl.)

A single Runecape screenshot from 2006 on Windows 98. Only rediscovered that on an old hard drive 2-3 years ago.

I have a bunch of old furry art by Doug Winger found when I was in high school still saved.

A 15 year old .exe that let’s you simulate a nuclear power plants fuel rod shields to try to start the reaction without going into a meltdown. Found it somewhere on the Internet after my physics teacher showed it to the class back then.

Music from Napster dial-up days is the only thing still in use that got forwarded to today. I absolutely have older files, but those will be school papers from the early ‘90s and the like and not in use.

A reference document from a Mac OS 8.6 computer in the 2000’s. It contains the pinout of every Mega Man Battle Network battle chip toy—a small and mostly useless piece of information, but definitely hard to find anywhere else, so I made sure to keep it.

I have the first song I ever torrented, purely for nostalgia. It’s been transferred over at least six computers and for a time, existed only on a flash drive that I originally found in a parking lot and kept.

The song? DC-10 by Audio Adrenaline. My mom overheard it and banned it from the house for being too violent. It was also the first time I paid attention to airplane platforms. Decades later, I work in aerospace and have done minor projects on the 747 and the KC-10 (extended tanker version of the DC-10 for military in-flight refueling).

The lyrics are pure 1990s Christian “punk”.

I still have a working copy of XNview.exe ported to every Windows PC I own. XNview was how you would copy & save a screenshot in Windows95.

Crazy that all the comments are either text files kept from the early-mid 90s or stuff from literally 5 years ago! Mine are mp3s I downloaded from RnB remux forums c. 2004-ish while in high school.

For me it has to be some MSX programs I saved to tape in the 80s. I had one that drew a map of my country and provinces inspired on the prefix map in a phonebook. I know, not impressive, but I was only 8 or 9.

My mother’s writings, in WordStar 4.0. Took some research to open and read them decently today.

Astonishing enough some old fart in love with WordStar not only created all the necessary conversion tools but even packaged WordStar 7 (the last existing release) so that it can be used today.

Edit: to put this in context, WordStar 4 used to run on an IBM compatible 8086 4.7Mhz PC, with wopping 640kb ram and 5.25 floppy disks. We already had an hard drive, some 16mb (iirc) beast that took two full 5.25 bay slots and was driven via MF/RL analog signals or something similar

I still have the floppy disk from which I’ve played scorch.exe in DOS from some time deep in my childhood, through windows 3.1 to 2000, then later mostly through virtual machines and retroarch on various flavors of Linux. Yes, I still have a floppy drive, so I could probably still play that file directly. I haven’t actually done that in a while, so the bits might have rotted. Every copy I have, kept on practically every machine I’ve made, is from that original floppy that I copied from a friend.