Probably this picture of my great grandparents. Should be from around the early 1900s.

Maybe one of my other family photos is older. My mother definitely still has some photos from the 1800s. But I don’t have those on file.

There may be something older, but I actually just ported over what may be the oldest files I kept around. In college around the turn of the century I did my last notable QBASIC program (I am an English major, though much more tech adjacent than most of my peers from the program are likely to have been), a rudimentary version of Sabaac, the card game from Star Wars, using the West End Games rules that are basically like glorified Blackjack. It’s super basic (LOL), and I honestly don’t recall if the computer is random or has a simple algorithm like Blackjack’s “if >= 17, stay, else hit.” The thing I was happiest about was a subroutine that takes in an external text file and converts it to a colored pixel from a palette of about 30-ish colors, so there is a deck of hexagonal cards in glorious MCGA.

Does 20 years old porn count as vintage porn?

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.

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

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.

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.

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”.

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

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.)

I have some zip and orb disks from when I was in elementary school. I probably still have the floppies with kid pix files I made in first or second grade.

No idea if they’ve lost data though.

I still have some texts that I wrote on the home computer on Windows 3.1. That stuff is probably 25 years old now.

I have the 5¼" floppies with my first programming projects in BASIC for the Commodore64. Not sure if those are still readable, but I also have a bunch of games I made in ZZT in the previous millennium.

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.

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.