Ecter's TrashSmells Like Windows Ninety
Games made to look like my fave era of a certain OS
My personal list of games with a certain "Windows 9x" feel to them. Not gonna list any that imitates Windows XP or later - there are way too many, while 9x is still somewhat rare (especially done well). This includes Windows 95, 98, 2000 and several versions of NT. Windows 3.0-3.11 and original desktop UIs may get a pass as well, but the game needs to earn it somehow (see: Kingsway). As a side note, if a game is free to play or has a demo, it's going to be mentioned near its release year.
If you're interested in a broader category that also includes Windows XP, other systems, or completely imaginary desktop UIs - there are other less exclusive lists of "simulated OS" games (which include some 9x lookalikes that i'm slowly going through and adding them to this page wherever it's appropriate). Meanwhile, i'm sticking to 9x below - mostly sorted by release dates and personal preferences.
My faves
- Kingsway (2017)
- It's just wonderful! It's a randomly generated adventure (so, "roguelike" in modern terms) played on a PC desktop. Visually it's its own thing, which blends GUI of several systems from 1990's, and it's all used for game's mechanics. Inventory management is done by dragging icons between windows. Sneak attacks and traps are pop-ups that you need to close to dodge / disarm them. Some enemy spells minimize your windows. Overall, the best in class for old system feel integrated with rpg-like gameplay! Further down there will be more examples of games that better answer the question "what gameplay fits old desktops the best", but this one succeeds in answering its own one - "how to make an rpg played through an old desktop feel right".
- It's just wonderful! It's a randomly generated adventure (so, "roguelike" in modern terms) played on a PC desktop. Visually it's its own thing, which blends GUI of several systems from 1990's, and it's all used for game's mechanics. Inventory management is done by dragging icons between windows. Sneak attacks and traps are pop-ups that you need to close to dodge / disarm them. Some enemy spells minimize your windows. Overall, the best in class for old system feel integrated with rpg-like gameplay! Further down there will be more examples of games that better answer the question "what gameplay fits old desktops the best", but this one succeeds in answering its own one - "how to make an rpg played through an old desktop feel right".
- Progressbar95 (2020)
- Found out about its existence when it was mentioned in a bsky thread where i gathered my list of win9x looking games for the first time.
Turns out it's pretty damn fun! It's a collection of minigames framed as a fictional "definitely not Windows" line of operating systems. It hits both my nostalgia for 9x AND 3.1/3.11! The main minigame where you play something similar to space invaders + centipede + breakout/arkanoid/alleyway by dragging a progress bar is neat on its own, but then there's also solitaire, two-color variant of minesweeper, not-wolfenstein, and-- and!!
It's a lot. I absolutely adore how it presents upgrades by unlocking legally distinct hardware. If i had to complain about things in it, there are three: Firstly, i disliked how it wasn't possible to disable CRT filter (eventualy it goes away after upgrading the monitor). Secondly, it was really confusing initially that paperclip serves both as tutorial character AND an enemy in the main game. And thirdly, optional e-mails (that are just a source of bonuses, so it's skippable if you prefer) are centered around roleplaying an office worker. I personally don't associate 90's systems with work, and, you know, i don't like to be reminded of work too much in my leisure time. Other than that - it's so damn good!
- Found out about its existence when it was mentioned in a bsky thread where i gathered my list of win9x looking games for the first time.
- Into The Deep Web (2021) (free)
- Simple, short and fun dungeon crawler that uses minesweeper board lookalike as a map. Wonderful idea!
Combat is somewhere between Kingsway and Dicey Dungeons and pretty easy to get the hang of. I'd love to see a longer game made out of it some day.
- Simple, short and fun dungeon crawler that uses minesweeper board lookalike as a map. Wonderful idea!
- dreamcore95idle.exe (2023) (free)
- Incremental game with an ending (so, the best kind!). Its interface and mechanics are pure "messing around with preinstalled software in win95", which i adore :3
- Incremental game with an ending (so, the best kind!). Its interface and mechanics are pure "messing around with preinstalled software in win95", which i adore :3
- TRAUMAKT~4.SEXE (2023) (free)
- This thing here is surely an unforgettable experience - at least it was for me. It features several styles of presentation (just check out the screenshots section on its itch page) and one of them happens to be a fictional medical OS with beautiful retro grey look. Its gameplay is also somewhat varied, but orbits around general "interactive fiction" territory (so visual novels and adventure games, with occasional first person exploration, turn based rpg fight etc.). Its story is positively unhinged and it's just elevated by this game's looks. Check out content warnings (they're not a joke) and give it a try if you're not put off by any of it :T
- This thing here is surely an unforgettable experience - at least it was for me. It features several styles of presentation (just check out the screenshots section on its itch page) and one of them happens to be a fictional medical OS with beautiful retro grey look. Its gameplay is also somewhat varied, but orbits around general "interactive fiction" territory (so visual novels and adventure games, with occasional first person exploration, turn based rpg fight etc.). Its story is positively unhinged and it's just elevated by this game's looks. Check out content warnings (they're not a joke) and give it a try if you're not put off by any of it :T
- Execute (2025) (demo)
- Content warning: genocide management software simulation. I think that's enough of a description for what it is thematically. It really does look like industrial software rather than desktop OS (something close to monitoring systems, or dedicated office software that i've seen in workplaces), but it specifically uses buttons and border styles of win9x. Gameplay-wise, it's something i'd call a decremental game - a subset of "incremental games with an ending", where the goal is to make the number go down. In this case, go down from population of billions to zero. It's morbid, and has performance issues at times, but i liked it for what it is.
- Content warning: genocide management software simulation. I think that's enough of a description for what it is thematically. It really does look like industrial software rather than desktop OS (something close to monitoring systems, or dedicated office software that i've seen in workplaces), but it specifically uses buttons and border styles of win9x. Gameplay-wise, it's something i'd call a decremental game - a subset of "incremental games with an ending", where the goal is to make the number go down. In this case, go down from population of billions to zero. It's morbid, and has performance issues at times, but i liked it for what it is.
- Identifile: Desktop Dungeon (in progress) (demo)
- I could say that's another arena survival like Desktop Survivors (see below), but this one goes in entirely another direction. First - its desktop is original creation (so, like Kingsway etc.), but still gets a pass since it's pretty flat and resembles 90's systems more than more modern ones. Second - its dungeon exploration part is done by moving through directory tree - folders are rooms, files are items, zips are locked rooms - extra point for interesting use of the fictional desktop there! And lastly, which is probably the most important part - combat is actually interesting. Once again you control a cursor, but you damage enemies (viruses and other malware) by drawing circles around them, quite like in Pokemon Ranger (or digging deeper - Qix, years before it). There are other "characters" (different kinds of cursor) with their own kinds of attacks, but the default one deserves praise for its lasso :)
Also: I'm counting it as "in progress" rather than released, because it's marked as early access on Steam. I found it fun enough to buy the full version though and i think it was worth it.
- I could say that's another arena survival like Desktop Survivors (see below), but this one goes in entirely another direction. First - its desktop is original creation (so, like Kingsway etc.), but still gets a pass since it's pretty flat and resembles 90's systems more than more modern ones. Second - its dungeon exploration part is done by moving through directory tree - folders are rooms, files are items, zips are locked rooms - extra point for interesting use of the fictional desktop there! And lastly, which is probably the most important part - combat is actually interesting. Once again you control a cursor, but you damage enemies (viruses and other malware) by drawing circles around them, quite like in Pokemon Ranger (or digging deeper - Qix, years before it). There are other "characters" (different kinds of cursor) with their own kinds of attacks, but the default one deserves praise for its lasso :)
Others that i played
- Microsoft Entertainment Pack for GameBoy Color (2001)
- Just a collection of games on GBC that uses win9x-like desktop as the game selection screen. Worth a mention here because it's a thing that MS released for Nintendo's handheld - an actual game that was on store shelves, not just a homebrew inspired by win9x! Pretty neat.
Since i can't link to a download here, have a gameplay video at least: https://www.youtube.com/watch?v=Z3UUnAtei40
- Just a collection of games on GBC that uses win9x-like desktop as the game selection screen. Worth a mention here because it's a thing that MS released for Nintendo's handheld - an actual game that was on store shelves, not just a homebrew inspired by win9x! Pretty neat.
- Zachtronics Solitaire Collection (2022)
- Pretty good collection of creative and unique solo card games. I'm putting this here mostly because of that UI featured as background in Sawayama Solitaire which comes from Last Call BBS - a game that probably would have been a better fit for this list, but i have never played it. But at least it got a side mention here. Huh!
- Pretty good collection of creative and unique solo card games. I'm putting this here mostly because of that UI featured as background in Sawayama Solitaire which comes from Last Call BBS - a game that probably would have been a better fit for this list, but i have never played it. But at least it got a side mention here. Huh!
- Desktop Survivors (2025) (demo)
- Not gonna go hard on this game, since it's in a genre that i usually don't enjoy (arena survival, so kind of a bullet hell adjacent) and i have only played its demo - treat it however you want. Just like Factory 95 (see below) it immediately got thumbs down from me for ugly pixel scaling. On the other hand, i like how it presents upgrades as opened programs on its taskbar, and that you move around the arena just by moving your cursor (i like the recent trend of hover-only games!). Visuals (in the demo at least) were kind of crude, but i actually count that as a positive trait, since it reminds me of independent games of 90's and early 2000's, mostly shareware or order-by-mail ones. Overall it's fun enough (probably more so if you like this kind of game), i recommend checking the demo out, but i did not end up liking it enough to buy it.
- Not gonna go hard on this game, since it's in a genre that i usually don't enjoy (arena survival, so kind of a bullet hell adjacent) and i have only played its demo - treat it however you want. Just like Factory 95 (see below) it immediately got thumbs down from me for ugly pixel scaling. On the other hand, i like how it presents upgrades as opened programs on its taskbar, and that you move around the arena just by moving your cursor (i like the recent trend of hover-only games!). Visuals (in the demo at least) were kind of crude, but i actually count that as a positive trait, since it reminds me of independent games of 90's and early 2000's, mostly shareware or order-by-mail ones. Overall it's fun enough (probably more so if you like this kind of game), i recommend checking the demo out, but i did not end up liking it enough to buy it.
- Factory 95 (in progress) (demo)
- It's a puzzle game presented as an automation/production style experience inside of an old win9x application. You get tasks delivered via e-mails, purchase upgrades in an online store - all in-universe of course.
While i appreciate the vibe that its author is going for - i did not like the demo enough to put it on that first list (it's somewhat fun, just not enough for a list of faves). Still worth taking a look at its demo if you like win9x-like look in games - just be warned that it looks very off because of poor scaling of UI elements (it's especially hard to look at if you enjoy pixel art, really), at least it did when i played it in late 2025.
- It's a puzzle game presented as an automation/production style experience inside of an old win9x application. You get tasks delivered via e-mails, purchase upgrades in an online store - all in-universe of course.
- Tabula (in progress) (demo)
- Another puzzle game, but this time it's similar to The Pedestrian in the sense that you move a character in the level built from parts that you drag and drop around the screen. It's presented on a desktop of an infected PC (like in Identifile, but it's also a theme that appears in other titles) and its taskbar and windows look almost like win9x, despite everything being presented in a limited greenish palette. I like how it uses almost no text and the tutorial is a single window that explains the controls - you gotta understand the goal on your own. It's interesting, and i'll probably get the full version when it comes out.
- Another puzzle game, but this time it's similar to The Pedestrian in the sense that you move a character in the level built from parts that you drag and drop around the screen. It's presented on a desktop of an infected PC (like in Identifile, but it's also a theme that appears in other titles) and its taskbar and windows look almost like win9x, despite everything being presented in a limited greenish palette. I like how it uses almost no text and the tutorial is a single window that explains the controls - you gotta understand the goal on your own. It's interesting, and i'll probably get the full version when it comes out.
Haven't played, but they seem to fit the theme
- Mario's Point and Click 64
- I'm scared of this thing. Linked retroachivements page, because that's the one with screenshots so you can see for yourself why it's on the list. I'm not gonna torture myself by playing it though.
- I'm scared of this thing. Linked retroachivements page, because that's the one with screenshots so you can see for yourself why it's on the list. I'm not gonna torture myself by playing it though.
- Home Safety Hotline (2024)
- Horror that uses 90's desktop UI. Never played it myself, but i appreciate the look.
- Horror that uses 90's desktop UI. Never played it myself, but i appreciate the look.
- Project RyME (2024) (demo)
- Similar to the previous entry, but it's a puzzle adventure rather than horror. I should check its demo out eventually ._.
- Similar to the previous entry, but it's a puzzle adventure rather than horror. I should check its demo out eventually ._.
- The Roottrees are Dead (2025)
- Another one to add to my wishlist. Seems to be a recurring theme to put a horror/investigation game in a mock win9x desktop, and i love that it's something of a trend now...!
- Another one to add to my wishlist. Seems to be a recurring theme to put a horror/investigation game in a mock win9x desktop, and i love that it's something of a trend now...!
- Pixel Pup (in progress)
- It's not out yet, but its "Nineties" pack immediately caught my attention! Firstly, because i love picross puzzles. Secondly, because it's another win9x looking game for Game Boy!
- It's not out yet, but its "Nineties" pack immediately caught my attention! Firstly, because i love picross puzzles. Secondly, because it's another win9x looking game for Game Boy!
Close, but no Chicago
- Her Story (2015): Points for teal desktop and pretty icons, but the windows are completely not that :T
- Pony Island (2016), No Players Online (2025): Desktop used for puzzles, but it's not win9x. Worth a mention because of their mechanics, though.
- Hypnospace Outlaw (2019): I could give it a pass like i did for Kingsway's "not exactly win9x but feels like it" UI, but, uhh. This one looks a bit too busy to fit the vibe i'm going for.
- OneShot: World Machine Edition (2024): I like the inclusion of a virtual desktop for the console release (also available for PC on Steam), but it's closer to earlier systems due to its mostly monochromatic UI. Gets a mention because it's not another XP lookalike :)
Not a game, but...!
- OMG that's so sweet! Game Boy QR Paint on Itch (free) - it is so damn clever and deserves a mention despite not being a game. It's a simple drawing tool for GB and its UI looks like win9x. I love this kind of creative stuff being made for old consoles <3
- Also, just in case you wanna get some 9x-like fun without leaving your browser: 98JS
Related lists
Other, more inclusive (any OS, real or fictional, not limited to 9x) and probably better maintained lists of games with interface looking like a desktop UI: