Does 20 years old porn count as vintage porn?
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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 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 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.
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.
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.
Dedication.
"He is a man focus, commitment and sheer fucking will"
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.)
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".
Hilarious your mom thought Audio Adrenaline was promoting violent lyrics.
I gotta say those lyrics feel a little "too soon" for someone living in Louisville with the UPS plane crash this week.
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 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 have a bunch of old furry art by Doug Winger found when I was in high school still saved.
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've got some early 2000s photos, and a torrent of Megas XLR somewhwre
- 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).
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.
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.
My music player still has songs that I once downloaded from LimeWire and some old pixel art that I made in Paint is on a hard drive somewhere. :D
I have some floppy disks from the early 90s which likely still work if I had a reader for them.
Likely not, the magnetism wears off after a few years.
Somewhere I have an image of a floppy disk containing the source and compiled version of a program I wrote for a Chaos Theory class in college in 1992.
It's a double pendulum simulator. Written in Turbo Pascal for MS Dos.
I wrote a rudimentary window management library for it. It had multiple panels for input and display. One panel allowed you to set the initial parameters for the pendulum (lengths, weights, position). One displayed the pendulum, there were a couple that displayed different graphs of the motion.
The last time I ran it was in the mid 2000's.
I have digital photos from the mid-90s. Back then I was shooting 35mm, but for a price, you could have the photos loaded on a floppy disk or CD-ROM. I might have the CDs around somewhere, but my computers can't read them. (I know, I could buy an external burner for like $30, I just haven't yet.) But I have them backed up on hard drives.
Now if you mean when the file was created, a bunch of computer users have games from the 80s. They might have downloaded the file in 2019, but the game was coded in the 1980s and the code has not been updated since, so does, say, Mario1.nes, count? Or old Atari games?
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.)
Anime from 2001...
There should be some MP3s from the mid-90s, but the date changed when I edited the metadata with winamp.
The oldest file I have available on my hdd right now that I made is an .XM (FastTracker 2) song I made I copied off a floppy a while ago, that's from 1995. Sadly there was a lot more where that came from but I lost them all in an HDD crash some time ago. I have a lot of older text files.

I created? I have pics from 2001 or so that are currently on my computer.
I also have various cds of shareware and game copies from mid 90s that are in a binder.
My old saves on the GBA emulator
Probably a music file or picture I downloaded in 2019/20. I lost the laptop I used as a teen, so couldn't transfer anything.
An early diary txt file I would email to myself as a safe off site storage approach.
I have some diaries I wrote on my PC in 1983/4. The PC was quite the thing - it had an amber screen rather than green, and two floppy drives. I can't remember what word processing program I was using, but haven't found a codec that displays a lot of the special characters.
I still have email from 1997, and probably a text file or two from 1995 along with some porn I got off of Usenet around the same time. I’m a digital packrat.
I have a photo of Adolf Hitler i downloaded some years ago for a meme that google photo dates back to 31 december 1938 so i guess thats pretty old
I still have the hard drive from my desktop computer back in 2003. So pretty much all the files there.