(The original top ten list: Part 1, Part 2, Part 3.)
Civilization
Many words have been spilled about this game's legendary ability to compel players to take "just one more turn." I've spilled many myself, and instead of spilling more, I will point you to the essays I wrote, each more elaborate than the last: 1995, 1998, 2011.
That first essay in 1995 was the start of a trend in my writing, where I'd play a very immersive computer game and then retell the experience in story form, with all the anthropomorphizing I'd done in my head along the way weaved in. It was a way for me to live the experience twice, and make a framework for pinning down the random thoughts I had about game design or philosophy - and of course the dumb jokes - along the way. Since then, of course, the internet has exploded with written and video-based play-alongs done by millions of people. I can't say I'm a trend setter because I don't think anyone of consequence ever read the things I made...
I also need to honorably mention the fifth game in this series, Civilization V, but for a different reason: It hooked me just as surely at the first game did, in a different era of my life, and infected me with a desire to travel across the world and see the ancient places name-dropped in the game. And that took further shape as a wild-eyed series of bicycle trips. A fair chunk of my middle-age time has been spent on a bike -- "behind bars" as we tourists sometimes call it. How much of that was Civilization goosing my interest in anthropology? I'll never know.
Robot Odyssey
It's circuit design as a game. Yep. How the heck could that ever be fun?
Well, you do it underground in the dark with obsessive-compulsive creatures. That makes it more relatable perhaps?
This game was extremely challenging. And I don't mean in terms of coordination or memorization - it wasn't about hitting buttons at just the right time, or repeating an action until you won by brute force - it was challenging in a legitimate engineering sense.
This game was marketed to 15-year-olds with the cute bloopy robots, but if you finished this game unaided, you were essentially performing electronic circuit design at an upper-division college level or beyond. The puzzles within would stump the majority of the adult population on the planet. And not because of cultural or language barriers either. Most adults simply would not be able to bend their minds around in the way required to solve these puzzles.
Robot Odyssey was like that arcade machine in the movie "The Last Starfighter": If you could beat this game, it was proof you had bona-fide real-life talent for engineering and could be useful in the industry almost immediately. I truly feel like the kids who finished it should have been subject to an aggressive recruiting push from Silicon Valley companies.
As a kid, I was also really taken with the idea that the things in the sewers of Robot Odyssey were intelligent creatures - up to a point - but they were also wired to automatically react in certain ways, just like the wiring of instinct in living things. If I put my hand in hot water, I instinctively recoil, and yet I'm still a thinking being who can process the event. So how much of life is being a robot? You do what you are wired to, and react the way you're wired to react, and your only option in life is to accept this and find some route to happiness or understanding.
Might and Magic / The Bard's Tale
These games take the fundamental weirdness of Dungeons And Dragons mythology and put it front and center, primarily through the colorful, playful artwork.
They made a perfect fit for computing: What better thing to convey, through a mathematical simulation on a flat, cold computer screen, indoors in a shadowy room, than an imaginary world where big hairy sweaty people were romping around in the sunshine, wearing exotic clothing, swinging giant clubs and sharpened hunks of metal, and beating on each other and screaming and shedding blood? It's about as far from the physical act of using a computer you can get. That's no coincidence.
I definitely can't say this applies to everyone, but I know for sure it applies to a significant chunk of the young computing population around me as I was growing up: We gravitated to sword-and-sorcery games on the computer because we liked the idea of being outdoors, with friends, with no bigger responsibilities than to physically bludgeon some certified evil antagonist until they either fled or died, and then sit around a campfire congratulating each other and making jokes, before doing the exact same thing again the next day. Of course, we couldn't really do that. The closest we got was camping trips, parties, and organized team sports, with the occasional schoolyard fight thrown in.
So we fed those urges indirectly, by doing something totally unrelated that we also liked: Sitting indoors quietly, going on internal mental journeys with the aid of the interactive digital fiction on the computer.
The more you think about it, the more - and less - sense it makes...
Chronotrigger
This game is a great realization of choose-your-own adventure storytelling. It's an open world -- sort of. The decisions you make are often mixed in with straightforward plotting, in a way that blends the two. Chronotrigger has won many awards over the years for its elegance.
But, this game has stuck with me for over 25 years mostly because of one incident that opened my eyes to the power of choice in game design.
Chronotrigger is a game about time travel. Early on you gain the ability to move between different eras of human development, like an anthropologist having the best dream ever, and later you gain access to a time machine that gives the characters finer control over where and when they go.
There is a character named Lucca. She's styled as a "nerdy scientist inventor" type, and she's instrumental to the plot of the game. There is a tragedy in her past: Her mother lost the use of her legs when Lucca was a child.
In the middle of the game, seemingly at random, all the protagonists are gathered around a campfire in a forest and the topic of Lucca's mother comes up. Everyone agrees it's tragic, and then they bed down for the night. The screen goes dark, and players naturally assume that the next thing they see will be the campground in the morning.
Instead the screen fades back in to the campground at night, with everyone asleep except for Lucca. She's up, and standing there. There is no music. With nothing happening, the player is compelled to poke a few controller buttons, and discovers that Lucca is now the character being played. The situation is clear: Lucca has unfinished business, and before she can sleep, there's something she must do.
After poking around, the player discovers that Lucca can walk away from the campsite and into the forest, where a time portal appears. She passes through it and the player is taken to a scene inside Lucca's childhood home.
The player guides the adult Lucca out onto an upstairs floor, with a view down to the workshop below. As we watch, a tiny child version of Lucca appears, helping her father with a machine. An accident happens, and the machine falls on top of Lucca's mother. The child begins running around, screaming, not knowing what to do. The machine needs to be shut off, but no one can get to the console.
Tragic music underscores the events that unfold. It is unclear what the player needs to do here. It's possible to explore the upstairs area a little and find a console that needs a password, and if the player guesses the password - Lucca's mother's name, Lara - then the machine is shut off and her mother is saved. But it is also possible - even likely - that the player will fail to figure this out in time, and the adult Lucca will be plunged back into the present moment in the forest, with no ability to go back a second time.
That's what happened to me. I didn't guess the password, and after a while of watching young Lucca run around screaming for her tragically injured mother, I was ejected into the present. All I could guide Lucca to do at that point was go back to the campground and bed down with the rest of the party. She'd revisited a terrible, formative moment from her own past, watched the tragedy all over again, and changed nothing.
I went on from that scene and continued the game, eventually finishing it, but the negative outcome stuck with me. Clearly something powerful had just occurred. Years later I learned that there had been academic papers written about that one scene, because the way it was designed was novel in gaming. It was an example of a new kind of narrative involvement in a tragedy, or perhaps just a really intense spin on a very ancient form of audience participation.
The player nominally has control over the character, and is responsible for the decisions and the effort the character makes, yet circumstances occur - maybe by design, maybe by choice - that make the character fail in their mission, and from that point on the character and the player are both forced to bear the burden of that failure together. The player has not just failed to find a happy ending, the player has personally failed a character they care about.
What made this incident special, aside from how novel it was in video games at the time, was how smartly it was handled. In the dialogue of the game, it's clear that Lucca is attempting to go back and correct a tragedy that she feels responsible for, and that was also formative in her personality. If - or when - the player guides her to fail in this effort, Lucca discusses it further with her friends the next morning, though she doesn't admit that she actually went back and tried to prevent it. The game actually shows Lucca trying to do the emotional processing that's needed to accept the failure, and again, since the player has been complicit in the failure, the player comes along for the ride.
Since that scene in Chronotrigger there have been endless examples of failure built in to video games, including failure with no possibility of positive outcomes, and many of these examples are reviled by players, who feel they are being railroaded into making poor choices or doing despicable things just for the sake of being hurt or even punished by the game designers. "The Last Of Us" is probably the biggest example of this in recent gaming. My own distaste for the way "The Last Of Us Part 1" ended was so great that I steered clear of "Part 2" entirely. It's bad enough that the main character selfishly invalidates everything you've accomplished over the course of the game. What makes it reprehensible, is that you are personally forced to move the controller and steer the character through that bad choice, even as you loathe it. Though you previously had control over whether they entered a room or fired their weapon, the game mechanics narrow down around you. There are many rooms but you can only steer into one. You have many possessions but the only one you can access is a weapon. And so on.
The worst examples of this tactic omit the emotional processing before and afterward. Like a tamagotchi showing a rotting digital corpse and declaring "YOU FAILED", with no comfort or guidance: What was the point? Why play a "game" if it makes you feel railroaded and sad afterwards?