Shadows Of Cairn (1994) is one of the worst games ever made, but specifically from that in-between tier, the most unfortunate one. It's not that it's a broken pile of shit - it's no Super Monkey Daibouken or Action 52. It's a perfectly playable game, it's just not fun to play - but it is aspirational, utterly unique, and it could have been a masterpiece.
My parents bought this game out of a bargain bin circa 1996, so I experienced it at the tender age of 8. I was absolutely baffled; at this point in my life I did not understand that one could have the skills to make a game, without it being a good game. This happened to me a lot with the NES; I played many titles that were absolute trash, and I just assumed that I Didn't Get It. It wasn't until decades later that I'd learn that some of them were considered Legendary Stinkers, or at least staggeringly hard, and that I was not to blame for failing to get anywhere.
Shadows of Cairn though... it's another animal entirely. It's not that I couldn't play it; I made significant progress in fact, many times. The problem was that I had no idea why I was playing it, because it lacked direction in both the literal and figurative senses. I always imagine that zoomers must struggle when they try to play PSX/PS2 era games because so many of them just drop you into a stage with zero indication of where to go. You can wander around for hours and hours in something like Castlevania: Lament of Innocence, never figure out what your objective is, and never progress because you just get lost and don't happen to click on the right door or whip the right statue. Shadows goes further however, because it's a goddamn open-world game developed in 1994.
I should mention that the game is definitely "FMV era," so it starts out with a cinematic with CD-quality voiceover explaining the plot. All the voice acting was done by various artists and programmers, of course, because this is a PC game; I'll muse on that point in a moment. The intro basically establishes that you're in this weird medieval fortress city built as a series of tiers, at the top of which lies the Duke's castle.

Following this, you're introduced to the main character in an in-engine cinematic. Had I been aware of the CD-i at the time, I would absolutely have pegged this as "CD-i as hell." Imagine if Animation Magic, the artists behind Zelda: The Faces Of Evil were competent artists and animators; it feels exactly like that. The characters were clearly drawn directly on the computer, at their native resolutions, with very simplistic tools, and while they don't get nearly as grotesque as their Zelda counterparts, you still see the occasional Freakishly Exaggerated Smile.
So let me make my point early: Shadows of Cairn is outsider art. It was made by a company with no other experience - they made a handful of card games and did a couple ports, but made no other "serious" games, if you will; this was their only original property. It was also made for the PC, which in 1994 was still not really a game platform. Yes, there were games, but to avoid dispute I will simply assert that the PC was not in the main stream.
The PC had struggled to become a game machine, but it had happened, and PC gaming was picking up steam very quickly - but it was still this weird thing happening off to the side, independent and isolated from the advancements in technology and culture of the console videogame world, where almost all mainstream game news was happening. I can assure you of this because I lived it, in perfect isolation - I grew up with PC games, I didn't know anyone with a game console, I didn't have any console-oriented magazines, and I didn't get any consoles (other than a dusty old NES) until I was like 19. I can tell you: I was pretty embarrassed to learn, in my 20s, of the many things that had been happening With Videogames while I was stuck on the PC with its weird alternate timeline.
There were good PC games, but they were... different. And I mean, if you ask me they were objectively worse, as far as action games go, because computer game devs of all types - be it PC, Amiga, C64, PC88, whatever - just did not take any of the lessons that console devs did from seminal games like Super Mario Bros. Any action-oriented computer game was pretty much cursed to have awful controls: Late jumps, poor air control, missed inputs, you name it, computer action games were just really bad at Moving Your Boy.
But they were also vastly different in tone. Starting in the mid 90s in particular, PC games got much darker than most of what came out for consoles, and I think this is because nobody was paying attention. PC game studios really did not become a significant market force on par with consoles until the 2000s, and the tight developer-publisher relationships that were already very normal in the console world just didn't really exist yet. In 1994, PC game studios were often still just six to ten guys in an apartment who'd work for eight months, then mail a floppy (or I guess a really early CD-R? or maybe just a whole hard drive?) to a publisher, then wait for a letter back saying "yes" or "no", with very little involvement in between. And I mean, what was the publisher going to do anyway - say "your game is too weird," when they just published some incomprehensible, unplayable shit like Pyrotechnica or Eternam?
PC games were weird, and they'd get much weirder before the wave rolled back. Before the 90s ended, PC game studios would put out a whole raft of incredibly unsettling games; my favorite example is Bad Mojo, where you play as a cockroach crawling around a series of nearly photorealistic screens representing the floor of a dive bar. One screen contains a lovingly detailed painting of an entire dead rat with a bloody razor blade sticking out of its neck. No console publisher would have tolerated that, even with an M rating - but as far as I can tell, PC publishers at this time consisted of exactly two types: "edutainment for kids" (75% of the market) and "what's a kid?" (the rest.) They just didn't care, as long as your game was playable.
Shadows of Cairn is playable, in the sense that you can get to the end without it crashing. As far as knowing what you're supposed to do at any given moment... yeah, not so much.
The beginning is linear enough. After the opening cinematic - establishing that your character is a would-be professional thief who's too ethical to steal anything, who then gets framed for a murder by his disappointed boss and now has to clear his name - you're simply dropped into the city. You could, conceivably, just wander around here endlessly. The only info you're given is a little icon in the upper left showing a wooden sign with a picture of a dog and the text "Shambles N."
You are supposed to take this to mean that you're to go to the lowest tier of the city (the Shambles) and proceed left or right until your compass reads N, then look for the sign with the dog's face. But you can ignore that, or fail to understand it (it's not described in-game, of course, you have to realize there is a manual and go read it) and become utterly lost, immediately.
The game is best described as a "prince of persialike" in the sense that, like that game, it uses what we would now call "animation-priority movement." The protagonist (Quinn) moves only at a realistic human pace and gait, each step is a separate action, jumps require a running start and don't go very far, the works. When you press a direction it takes time to get up to speed, to stop, to change direction, etc. Another thing you can do is climb; the city is made of brick walls, and Quinn can scale them, one agonizing foothold at a time. This is your primary method of navigation in the game, climbing up and down from tier to tier.
You start out at ground level, and while you're supposed to go through the sewers to get into the city, you can instead just turn to the wall and begin climbing it. At the top there are pikemen who will kill you, and you can waste hours here thinking you're doing something wrong, when in fact you're just not supposed to be going that way. But if you play the game on Very Easy mode, like a child very likely would, you are offered an invincibility cheat right from the get-go which will allow you to go right past those soldiers and begin exploring the city. I'm pretty sure this sequence-breaks the game and probably causes problems, but I've never checked. In any case, the entire game world is completely open to you and you can go anywhere.
The world is highly realistic, in the "we were thinking more about the word 'realistic' than about how to make a fun game" way. As far as I can tell this game contains very little Content - basically just four areas, you can finish it in an hour if you know what to do - but the world is expansive.
Each tier of the city consists of a single road, bordered on both sides by buildings and houses. This exists at a realistic scale, so there are dozens of buildings on each tier, and it takes several minutes to walk from one end to the other... at which point you turn and walk down another street, because the city is square. There's four sides to each tier, so there have to be hundreds of buildings in this game, and none of them do anything whatsoever, as far as I know.
There's no indication of this however. You have no idea that none of it matters, that it's all just decoration around an incredibly tiny game, and nothing stops you from simply wandering into it and becoming completely and irreparably lost. Every street also has multiple vantage points: you start out looking "inwards", towards the wall of the next tier, but you can turn around and look out towards the lower tier, and you can walk between the buildings, which will put you in an alley behind them looking out, and then turn around again to face "inwards" towards the wall to scale to the next tier. So there's basically four layers and four sides to each tier, and with something like 9 tiers, there's a total of 144 perspectives, each of which takes several minutes to traverse fully. You could spend dozens of hours just exploring the game world fully. And there's nothing to do in any of it.
The alleys are full of barrels with stuff sticking out of them; you can't look at or pick any of it up. They even bothered to make the buildings distinct; signs indicate clothing shops, jewelers, bakeries, and as you proceed up the tiers you get to the more expensive houses which look completely different, so it's all beautifully and lovingly realized, it screams "lore, and lots of it," but it's utterly opaque. There are no diaries to read, no NPCs to interact with, and you can't enter or interact with anything - you are, after all, a failed thief, so you aren't actually interested in stealing anything.
The game consists of about six story beats, each one containing a single objective, and the only goal is to get to that objective. To their credit, the devs realized this was impossible without some guidance, so there is actually a quest tracker of sorts - that little icon in the corner with the street name tells you exactly where to go. So the game just consists of you passing through an utterly inert world on your way to these objectives. On Very Easy, you can even click the icon to go straight there. They built this entire world which has no reason to exist, and can even be bypassed.
It's particularly sad when you realize that the devs felt completely unrestrained by game design conventions. Again, I feel that PC developers were just not looking at what console devs were doing and didn't really know what "best practices" were, and the game is thus completely unafraid of taking a Bill Watterson approach to graphics, altering the "comic frame" whenever it feels like it.
The aspect ratio of the game's viewport changes constantly; sewers and the insides of buildings are portrayed at a nearly 2:1 ratio to reflect the short ceilings, while the castle has much taller, grander rooms, and the outside world fills your entire screen. The game scrolls horizontally and vertically when exploring the streets (though mostly in the flip-screen style, since this was developed before PCs had blitter hardware) so despite the low resolutions of the time, each outside area is simply enormous.
This is most easily seen in the Windows version, since it's happy to display at any resolution you like.

Here it is running on my 2K ultrawide; that's 3440x892. Early Windows games were wild.
The amount of art and effort put into this world conflicts with the amount of actual game content; I suspect strongly that the developers had much greater ambitions, which were scuttled by lack of money and time. I wonder what they could have been however - while this game world is beautiful, it's hard to imagine what game would have taken place here. I'd love to have seen what they had in mind, but unfortunately, all we have is the game that got published.
What you are supposed to do at the beginning of the game is to go into the dog's-face tavern, which then drops you into a sewer level. Because of course there has to be a sewer level, and of course it's miserable and would put anyone off this game before they even started. It does however contain one of the funniest and most inexplicable interactions I've seen in a game in my life.

Entering the sewers, you meet a nutty old man living there, who accosts you and demands that you go retrieve his dog from a guy who stole him, and in exchange he will give you "something of great worth." So you run off to the right... and immediately fall through a hole into the water, and a monster eats you. Reload, do it again. You have to jump over two or three holes (it never gets easier, the game drops inputs constantly) before you find the guy.

It turns out the "dog" is a rat; specifically, the strangest drawing of a rat I've ever seen. As a child this captivated me; why does he look like that? I don't know, but obviously I love him.
Much like Prince of Persia, you switch into a very wooden and awkward Fighting Mode. The game's combat sucks, but it has a saving grace: as soon as you enter combat mode, it immediately kicks in AN INCREDIBLY SICK FIGHT SONG.
Did I mention that the entire soundtrack to this game is Fully Anachronistic? Please flip through that playlist; the game sounds amazing. "The Thief" is a 14 minute guitar-chugging saga that could only have been composed in the 90s. Dudes very literally rock.
So, you beat up the guy, take the rat, return it to the old man, and he thanks you and hands you a pair of daggers.
Quinn says, "Thanks... what are they?"
The old man replies: "Knives, idiot!"
It's absolutely spellbinding. Why did they put this in the game? Why wouldn't Quinn know what a knife is? What possible trait are they trying to establish for this character? Is he just dense? I have no idea, and again, I experienced this at age 8. I don't know what's going on with it now, imagine how I felt then.
After that, you run through the sewers. For what feels like hours. Turn after turn after turn, you're just running and running and running and running and running, endlessly. I don't know how many screens it is; it feels like forty or fifty. You don't do anything, you just run, jump over holes, and avoid slime monsters who will kill you in one hit. There is no more combat, no switches to flip, no maze, you just go forward forever until you find the exit.
This is why the game is not fun, in a nutshell. There is nothing to do. I'm sure the devs had ideas that didn't pan out, so they did what many early game devs did: "just put in a big stupid maze." This game pretty much consists of about 15 minutes of actual Content wrapped up in three incredibly stupid mazes. There's the sewer, then you're sent on a very simple fetch quest by one of the three NPCs in the entire game, then you go through a dungeon maze, then the NPC sends you to The Wizard.
You go through a tedious hedge maze, then enter the wizard's tower. This turns out to be another maze, and the best kind: A teleporter maze!
I think I made it here once, as a kid. I now know that I had no chance in hell of getting through it; there are dozens and dozens of rooms with no indication whatsoever, that I'm aware of, on where to go. There is no map (are you kidding) and I don't think any other indication of what you're supposed to do. Like most teleporter mazes there is simply no way to keep track of where you are or where anything connects, but unlike most others, this maze seems to contain a vast quantity of them.
Here's what a walkthrough suggests:
*teleport from room 3 to room 4. Then go two screens right. *enter the right teleporter in room 6 and arrive in room 23 *teleport from 23 to 32. Go one screen right. *teleport from room 33 to room 37 *take the right teleporter from 37 to room 42. Go one screen left. *teleport from 41 to room 47 *take right teleporter from 47 to room 50 *teleport from 50 to room 53 *teleport from 53 to room 52. This allows you to avoid the traps in room 52. *teleport from 52 to 56 *teleport from 56 to 58 *teleport from 58 to 62 *take right teleporter from 62 to 66. Go left and enter the doorway. *teleport from 64 to 68 *teleport from 68 to 72. Go left and avoid the traps while passing through room 71. *teleport from 70 to 75 *teleport from 75 to 78 *take right teleporter from 78 to 80 *take left teleporter from 80 to 84 *teleport from 84 to 86 *teleport from 86 to 90. Take right doorway, take another right doorway to 88 and get the herbs from the trunk. *teleport from 88 to 93 *take left teleporter from 93 to 94. Go two screens right to room 96 and get the scroll. Go two screens left to 94. *take the right teleporter from 94 to 99 *teleport from 99 to 101 *teleport from 101 to 103 *take right teleporter from 103 to 108 *take right teleporter from 108 to 109 *teleport from 109 to 112. Go through the door and go right to 114 and get the scroll. Go back left to 113. *teleport from 113 to 115. Go right and through door to 117. *teleport from 117 to 118. Go down screen to 120 and get the herbs. *teleport from 120 and enter the hedge maze.Yeah. I don't get it either. It's also infested with enemies, and when you exit, you have to go through another, even bigger hedge maze to get out, also full of enemies.
And that's just about it. You break into the castle, kill some guards, have an anticlimactic battle with your boss and betrayer, and just like that your name is cleared, for some reason, and the duke knights you and lets you marry his daughter.
It's a mess. I have no doubt that huge chunks of the originally intended game are missing, replaced with these miserable timesink mazes just so they could ship something, but even if the devs had made exactly what they had in mind, I'm sure it would have been a slog that would not be remembered well.
But it is outsider art, and I value that deeply. It is unlike anything else I've ever seen, in countless ways, and I believe it's for that reason I gave earlier, that PC developers were just off in their own world, not knowing what was "the right way" to do things and just coming up with shit. It has that "mid resolution" pixel art style that existed for just a couple years in the late-dos-early-Windows era; it has arguably quite competent and distinct animated cutscenes; the characters (for what little you see of them) are surprisingly compelling if you ask me; and despite the voice actors just being "whoever was around," I sincerely enjoy the voice work. But most importantly, the atmosphere of the game world hits like a truck.
When people talk about Dark Fantasy it's usually along the lines of Dark Souls, where everyone is miserable at a cosmic scale, as in, the actual fundaments of the universe are crumbling and those who are alive at all are not having anything like what you'd call "a life." Or it's some Game of Thrones bullshit where the "dark" is just "people get their nuts burned off in hot oil" and other modern-TV-misery-porn nonsense.
Shadows of Cairn fascinates me, almost 30 years after I first played it, because of its sheer bleakness. Some of this is surely due to the game being obviously incomplete, but I think it would have come through anyway.
In addition to being a very raw and realistic-feeling medieval world, a thing you don't see that often in games, there is something... dead about this place, a kind of Langoliers energy, as if you're in a world that's slated for demolition. There are lots of games that feel empty, but this one just hits different. I think a lot of that is due to the very strange art style, in which the entire world is lit by an unseen ambient light source.
The outdoors is blasted with light and hard shadows, as if there's an enormous 10,000 watt softbox light parked a foot to the left of the 'camera' even though the whole game takes place at midnight and there are no streetlights or lamps. The indoors gets the same treatment, and the result is a dingy, static feeling, like a stuffy attic illuminated by too many fluorescent tubes.
The city is also absolutely deserted. Except for the couple NPCs, which seem to be posted up at their places of 'business' as if it's the middle of the work day, there's nobody around except the guards, who never make any sound, just trundle toward you and start poking with their spears. They can also throw them, in which case you most certainly will die, but there's no animation for this; the spear just passes through you as you unceremoniously collapse.
Everything feels odd and off-kilter. It's like a perfect world inhabited by no one; you feel like, if you were able to enter any of the buildings, they would just be blank grey boxes with no decoration. It's unsettling, in a way that was surely not intended, but sticks in ones craw. I would like to play a game that looks and feels like this. Just not this one.

