Selected Edutainment of My Childhood
Reviewing the best learning games the late 90's and early 2000s had to offer. Or, at least the ones my parents stumbled upon.
The past few weeks I’ve been deep in the books researching my first lesson (on the 1980-81 Polish Solidarity movement) for Flashbang, my spaced repetition-first learning platform.
In the background, I’ve also been revisiting some of my favorite childhood edutainment, hunting for good examples of learning design. In a few weeks, I should have some exciting updates on what I’m building. For now, some nostalgia. There’s some real treasure in here.
- Joe
Wishbone’s Amazing Odyssey
Game Concept
You’re the famed Jack Russell Terrier of the PBS kid’s show, sucked into an ancient literature simulator that puts you in the sandals of Odysseus at the start of Homer’s Odyssey. It’s a point-and-click adventure game where you solve puzzles that each correspond to different parts of the story, leading to your triumphant return home to your wife.
Fun Level
God tier. The puzzles were designed by people who prioritized the child’s experience. Many similar games, unaccountable in this respect as they are, design puzzles for the enjoyment of the adult game designers. These puzzles are the right level of difficulty for a dedicated child ~9 or so—which isn’t to say they’re easy.
Even better, the game is *spooky*. Odysseus’s crew get swallowed by Cyclops, drowned in Charybdis, and sent to Hades by wrathful gods. No matter what you do, your staff thins out over the course of the adventure.
As a kid I let my starving crew eat the cattle of the sun god and remember being viscerally disturbed by the game over screen I earned, in which we all were doomed to a vengeance too horrible to name. You really gotta hand it to em.
Learning Level
Also premium. I think their task is well-suited to a video game, which made this an easier goal to hit. Learning the beats of a well-worn story is easier to accomplish while point-and-click adventuring than, say, the basics of biology.
Total Score
I’m starting the review off with my favorite. No video game south of Disco Elysium has captured my imagination like the Dog Odyssey, to this day.
4/4
Encarta’s Mind Maze
Game Concept
An add-on to the Microsoft Encarta encyclopedia suite, this procedurally generated maze advances you through a castle dungeon by answering questions about the contents of the encyclopedia.
Fun Level
Pretty mid. What child’s going to memorize these facts? I remember setting the trivia categories to “Sports, Hobbies, and Pets” because I knew their questions sets were smaller, so that I could memorize the answers.
Learning Level
Basically none.
Total Score
It earns some points from the wonder you experience stumbling across this tucked-away game in an encyclopedia. The accidental way in which I discovered it pushed me forward even when I slogged through sports trivia.
2/4
Maurice Ashley Teaches Chess
Game Concept
The designers of this game included just about everything a child would need to learn to play and love chess. The practice sections teach you fast and drill your fundamentals sports-style, but my favorite sections were the master games, which someone on YouTube was kind enough to record.
Fun Level
Pretty great. Short of some kind of ‘story mode’ or other motivators to play and win, I don’t know how they could’ve made chess any more fun.
More than anything else, watching this outrageous game of Tal’s, the ‘Magician From Riga,’ turned me into an absolute obsessive.
Learning Level
You learn chess very fast, and learn the basic strategic/tactical ideas quickly too. The sports metaphors help make the concepts stick, even for non sportsfans.
Total Score
Ignited a lifelong love of chess I hold to this day. 3.5/4
Bill Nye’s Stop the Rock!
Game Concept
A first person point and click adventure game where you’re in Bill Nye Laboratories after a rogue AGI sends a meteor (“Impending Dume”) hurtling toward earth. You have to solve its riddles to save the planet.
Fun Level
Very fun just to walk around and explore, even if I found the content a little too zany to follow at times.
Learning Level
The whole set is full of tiny science experiments and factoids. However, the puzzles were a little too clever for how old I was when I got it. It really is difficult to make the actual bits and pieces of the puzzles interface properly with a little kid’s mind. I beat maybe one of the AGI’s handful of riddles. I mainly just looked around.
Total Score
3/4
Window’s 3D Movie Maker
Game Concept
It’s a kid’s movie-making software that, brilliantly, comes with a bizarre open world full of weird characters to explore while you make your movies.
Fun Level
Very high. The world of the movie set, theater, and related side alleyways and curious pitstops is full of weird, mysterious, interesting stuff. The lack of an agenda/games or puzzles makes it somehow more engaging.
Learning Level
Well, there wasn’t much content we were expected to pick up. But I made a ton of movies with this thing. The movie editor, which you can see in the clip above, is surprisingly sophisticated for something from 1995.
Total Score
A masterclass on how you should surround your tool/core product with a fun little open world and some lore to keep it company. 3.5/4
Amazon Trail, 3rd Edition
Game Concept
A slick remix of the Oregon Trail in which you have to make it through the Amazon river. You pick a tour guide and then need to manage your rations, food, keep from getting sick, etc.
Fun Level
There was definitely enough challenge and intrigue to warrant seeing how far I could get. But in some ways it felt unclear how to strategize—I didn’t know which choices were better than others.

Learning Level
Of all these games, this one was one of the more purposefully educational. You could definitely picture it in a school computer lab. However, it did seem like a lot of the factoids were overlayed on top of the gameplay and not baked directly in. You can get out of your boat and go learn about Amazonian wildlife, for instance, but I don’t remember it helping your score go up.
Total Score
An immersive feeling of adventure, but not enough juice to keep me playing. 2.5/4
Special Mention: U to U
Show Concept
Your reward for making it this far is to hear about the single most underrated, ahead-of-its-time creation of the golden age of children’s television.
This one isn’t a game but instead an insanely forward-thinking TV show on Nickelodeon. U to U only ran for a couple years in the mid-90s, but we will collectively only be ready for its ideas sometime in the late 2030s, after we’ve stopped damaging our children with social media.
“Welcome to U to U,” the show’s co-host Sertrone Starks says, “the kid created, interactive, onlining, globally connected—”
“Wait wait wait,” co-host Ali Rivera interrupts. “You mean the place where kids have creative control? Because all the songs, stories, poems, jokes—everything on U to U comes from kids?”
“Precisely. In fact, if you look around the core, our super database where all kid connections are processed, you’ll see everything you send us on the control tower and your name on the message board.”
It was like a single, benevolently moderated, well-curated worldwide televised internet forum for kids. Absolutely genius.
Years later, projects like 826 Valencia would take similar tacks—children would come to the after school center, write a short story, and professional illustrators, editors, and book-binders would help them shape it into a professional art product.
But U2U was unique in its techno-optimism—for instance, in its determination to collect artwork from kids in multiple continents, serving as a kind of electronic pen pal hub. Children designed video games, short films, animated cartoons. Everyone was clearly very excited about the possibilities of the internet. Its high-energy, variety show atmosphere captured my imagination as a child like nothing else on TV did.
Check out this YouTube comment under one of the archived episodes:
GPAnimations, it appears, has since gone on to illustrate professionally. Good job, U to U.
In the future I may dig around these archives some more and present the results of more serious research. It deserved better than a two year run.
Total Score
5/4 - Someone really should bring this back.





I had completely forgotten about The Amazon Trail. I spent many hours on that game so thanks for the nostalgia
I remember Wishbone from tv! I never really had any good edutainment games though. I think the best was Math Blaster. After that all I had was Brain Age and a crappy SAT Prep game for the DS.