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.

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.

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 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.

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.)

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’ve got some early 2000s photos, and a torrent of Megas XLR somewhwre

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.

deleted by creator

I have an mp3 I downloaded off some random website in 1999, before I even started using Napster. It’s a cover of “Whiskey in the Jar” by some pop-punk sounding band with a heavy German accent that was labelled “Ernies” on the file, but who knows.

I’ve got a couple of files from the '80s originally created with AppleWorks. I can open some of them with LibreOffice (yay for opensource!), for some of the others I have to use Sheepshaver (Mac OS 9 emulator). I keep them for nostalgia reasons.

• 1993 reading notes on Plato’s Republic (Word 5.5 or 6? I can’t remember, it was on a Mac).
• 1 scanned class picture from 1979 or 1978 (the scan was made in the mid to late 90s).

Oldest file created digitally is probably some photos from 2020. Idk why I didn’t save photos before then, probably didn’t value memories that much back then.

I have un-digitalized photos from like… 2005/2006? Including the tine when my family apparantly visited Hong Kong, but I only have vague memories of. (Do these technically count as “files”? You didn’t specify it has to be digital…)

The oldest oldest file is a Geneology book in .pdf format digitalized from paper, the papers is probably at least 100 years old, pages are deteriorating. The actual info from it spans few generations back, like 1200s. It shows all the male ancestors and all their male decendents. Apparantly, according to the info, a lot of people in my village, many who have a blood connection with me, are living overseas… fun fact I guess…

(Also, notice how I said it’s males only? Patriarchy runs deep…if I was a girl, I wouldn’t be listed in the geneology book, and any future decendents of women definitely won’t get added.)

Does 20 years old porn count as vintage porn?