**Backdated for historical purposes**
A somewhat advanced pencil sketch from me at the time, I don’t quite recall what got me into chess. I think it was a game box that my family had gotten with various board games, that did include chess. I also do recall that we had gotten a game called Chessmaster 4000, whose aesthetics do match up with the lightning and everything.
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This was a welcome discovery when archiving my diskettes during the pandemic.
Apparently I made this masterpiece with clipart off of a Softdisk Publishing disk we’d received in the mail. I was heavily influenced by the Drivin’ USA game that was popular at the time, which had multiple arcade cabinets in almost every pizza place and Walmart I stepped foot in.
This feels like one of these pieces that I want to recreate with my art style one day. The idea of this sky-high highway just shows a bit how my mind was working. Which is important to me with all the thing’s that’s happened in life so far.
I’m also noting that this was almost exactly 30 years from this image’s creation if I’d posted it one year later.
Done in Paint on a Windows 3.11 machine, likely an IBM PS/2 65sx.
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I don’t know who this would’ve been for, as in 2026 I have no recollection of anyone’s birthday in April 16th. It wasn’t anyone in the house back then. I give my younger self credit for being generous with digital art.
But the concept was actually pretty simple; I’ve heard a cousin talk about the Chesapeake Bay Tunnel while going someplace, and how it’d gone underwater for a few miles. This was amazing for me at the time, as the only reference I had for tunnels was going into New York City.
This was completely drummed out of my imagination, but to try to portray something from the real world. I had absolutely nothing to use for reference for this; there were no books in the library, and there was no Internet. All I had were Paint skills and the car clipart.
You can see how I even tried to get the concrete dividers with that sand color they’d typically have, but I couldn’t come with a close enough color.
Done in Paint on a Windows 3.11 machine, likely an IBM PS/2 65sx.
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Remember that spiffy game called Descent? With the ship flying around in the cavern shooting robots? I got a whiff of it and thought it was intoxicating. While I couldn’t play it at home, the memory stuck with me long after. And while I had barely been drawing things in MSPaint, one night I did drum this up on my parent’s IBM 65sx PS/2 system, and had forgotten about it till a diskette dump I did in 2014; a BMP fanart of Descent.
I had seen the game briefly in action at a relative’s house in Charlotte. And while I would die within ten minutes of starting Level 1, those gray hallways and that Spider Bot in the menu always stuck to me. While I’m pretty sure I might’ve drawn something on paper, I apparently did this in MSPaint as well. Why, I don’t know; but I did, and I did write and save it to a floppy disk to uncover all these years later.
As you can see, the imagination of a kid holds a lot of potential. They can remember certain things very well and vividly in those times. The cockpit may be well off, but I certainly remembered that double ring HUD. And I even got the ship design right in the shield window to some degree. Looking back at it decades later, I can’t believe it myself that I did ‘fanart’.
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Super simple, straightforward piece of art I tried to do in Windows 3.11 back in the day.
I don’t think I did that bad considering it was mouse-drawn, I obviously failed to sign my name on the bottom, and it looks like I outlined the body then it got colored white with the flipper. I’m pretty sure I had Kenny at the time, so I might’ve used that for a reference as well. The red eye was likely because the brown wasn’t working on the computer’s VGA scheme (I’m thinking it wasn’t 256 colors), so red it was.
Done in Paint on a Windows 3.11 machine, likely an IBM PS/2 65sx.
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This abberation known as “Oatman” survived during a recent floppy transfer. I had no idea any of my old art existed anymore, so this was a big treat. MS Paint, Windows 3.11
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I should do a #redraw challenge and redo this character with my skills now.
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As a disclaimer, these post titles are what the original files were named as. I only deviate if I know the piece had a specific name or title.
With that, I have no idea what “POP” was supposed to mean, but you have a space battle almost befitting of Ancient Aliens going on here. I’m pretty sure all the planets were meant to be in the image like classic sci-fi. You have a Concorde-esque like space cruiser with the ‘droop snoot’, under attack by a variety of starfighters. One has a very practical, Starfox-like appearance, while the other carries that “bird form” look with the wings.
I have no idea what’s going on with the planet’s surface, but I’m going to guess those are some dirt highway. It might also be band striping on planets or a mountain range, considering it sticks up on the horizon.
And that explosion I’m pretty sure is the space cruiser having launched a fighter to combat the other ships, but it got blown up right after. I’m pretty sure there was a nod to an animal design too, considering the nose was cold and the back end was brown like an eagle.
Lots of action in a 1996 piece, right?
From the file’s date, I have a sneaking suspicion this file may not have been created at home. It’s very likely this was made at a relatives house, likely my Mom’s family in New Jersey with their PS/2 tower.
Done in Paint on a Windows 3.11 machine.
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Except for my ORCA and BRTHDY16 piece, this was the only “close to reality” digital kid art I did from what I recovered.
Sure, it depicts me essentially driving a Shoprite truck, but I was a kid driving said truck. This was also not a short cab, being those sleeper cab types that I’d see on the road while traveling all the time.
No space battles, no outer space anything.
Just little me driving a repainted truck in livery of a real toy I had.
You can see I goofed up the hose hookups on the trailer with the green spot, likely going to erase them then being greeted with white space. So I had to fill it up with grass to keep the look.
I’m impressed with my 10-year-old self that I almost mimicked the Shop-Rite font for the time. I know it’s not exact, but it feels that it was old enough that I may have seen it someplace.
But the funny thing? I have dabbled in American Truck Simulator from time to time. I got it as a freebie from someone in an Elite: Dangerous gaming group, but never bothered to dust it off till October 2025. Admittedly I have thought of part-time truck driving with the way work has gone in the world, but I don’t think I’d be up for backing up a trailer into a dock.
Again with the date of this file, I think I made this in New Jersey on my relative’s PS/2, likely in the evening when everyone was visiting. There was no way I was using the computer this late unless something special was going on.
Done in Paint on a Windows 3.11 machine, likely an IBM PS/2 65sx.
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I’m actually surprised this survived. This is the earliest evidence I have of consistent worldbuilding digitally.
At the time, I had the idea for this space-faring organization with their own motives. While they generally were good-leaning, they weren’t goody two-shoes like most heroes of the time. While I had no concept of this at the time, you can equate them to gray-area special ops teams like in this modern day and age.
I was aware of Star Fox at the time, and this drew partial inspiration from that. There was also a video game I have no idea was that I’d seen on the NES, which also lent to its inspiration.
Either rate, this organization employed ships known as Cannonballs; rightly named for being able to ram through smaller ships and disintegrate them. They were very difficult to shoot down to having strong hulls to make such a feat, but they had trade offs. Very simple weapons that might’ve been useless, no cargo space and barely enough room for two. I very much thought of them as a sports car to a point, much like a Mitsubishi Lancer or the like.
Little did I know growing up, that Northrop would test the XP-79, which was a specialized aircraft to ram enemy bombers in 1945. I only became aware of this concept in 2023, which I’m sure I have in my “to-do” bookmark pile somewhere.
I guess bright minds can come up with similar ideas.
Also again real funny business going on with this file; it’s last edit date was after midnight. Something special had to be going on then
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One of the things I always wanted as a kid was a train set. This came about after an uncle gave my Dad some leftover parts of a defunct train set. All I had was the caboose and one track length to play with. Later on another uncle did provide a cheaper complete set that I could fool around with to a point, which was fun till the engine broke (it was some generic battery-operated store brand, I think).
Since then, I’ve always wanted a proper one to fool around with till about my later teenage years. This is me trying to imagine a new, complete store-bought train with the imagined bits of the old one I had. While I now realize a modern electric train wouldn’t be hauling a steam train caboose and coal car, little me was creative enough to smack old and new together.
My name's Janeil.
Welcome to my part of the galaxy.
Moonlight game dev, creative writer, sharing my personal experiences.