10 Surreal Retro Games You Can Play For Free
Welcome to the forgotten frontier of surreal software. Before the internet fully engulfed our attention, there were games and “interactive experiences” that lived on floppy disks and jewel case CDs. Fever dreams of edutainment, corporate surrealism, and polygonal psychedelia.
These digital pieces of art were half-educational, half-psychedelia. Today, many of them are preserved on the Internet Archive for you to explore.
Here are 10 of the most surreal, uncanny, and aesthetically powerful DOS and Windows 95 games you can revisit—or experience for the very first time.
1. Eastern Mind: The Lost Souls of Tong Nou (1994)
Created by Japanese multimedia artist Osamu Sato, Eastern Mind is an existential point-and-click trip through a sentient island shaped like a giant head. You play as Rin, a soul without a body, who must reincarnate nine times to reclaim his identity. Everything—the puzzles, the soundtrack, the visuals—is a surrealist meditation on death, transformation, and digital reincarnation.
2. Encarta MindMaze (1998)
Hidden inside Microsoft Encarta '95 and 98, MindMaze was an educational trivia game disguised as a medieval quest. But what made it surreal wasn’t the questions—it was the mood. Stone corridors looped endlessly. NPCs whispered trivia in faded JPEG form. And the whole thing felt like wandering through a castle of forgotten knowledge.
3. 3D Movie Maker (1995)
Microsoft's 3D Movie Maker was a sandbox dreamworld where kids could animate their own films using Claymation-style characters, surreal props, and VHS-style effects. It was clunky, slow, and deeply weird—and that’s what made it beautiful. There’s now an active community reviving this program for a new generation of glitch artists and retro creators.
4. Phantasmagoria (1995)
An interactive horror movie by Sierra, Phantasmagoria blends live-action performances with CGI environments and FMV death scenes. You play a writer exploring a haunted mansion filled with increasingly disturbing rituals. It’s slow, moody, and filled with strange dream logic—like Twin Peaks meets Myst.
5. Commander Keen in Keen Dreams (1991)
While most platformers of the era were cheerful and colorful, Keen Dreams stood out as a kind of sleep-paralysis side-scroller. You play a boy trapped in a dream where vegetables have become fascist overlords. The pastel environments, bizarre enemy design, and floaty gravity make it feel more like an ambient fever dream than a game.
6. Chu-Teng (1995)
A spiritual sequel to Eastern Mind, Chu-Teng plunges even deeper into the mythos of reincarnated souls and sentient islands. With its vivid colors, alien UI, and cyclical death systems, it’s less of a game and more of a digital religious experience—perfectly aligned with Vapor95’s spirit of techno-mysticism.
7. Postal (1997)
Crossing into Windows 95 territory, Postal is a satirical, chaotic FPS that revels in absurdity and moral dissonance. Its bleak humor and surreal violence predate indie’s moral ambiguity.
8. Castle of Dr. Brain (1991)
This Sierra “edutainment” title disguises logic puzzles and math problems inside the mansion of a mad scientist. But it’s the vibe—the sterile tile floors, floating lab equipment, robotic mice, and broken machinery—that make this game feel like you’re wandering through a haunted educational mainframe.
9. I Have No Mouth, and I Must Scream (1995)
A horror-adventure co-crafted by Harlan Ellison, this game traps five souls in an eternal torment engineered by a sentient AI named AM. Each character’s nightmare arc is a psychological spiral—unwinnable, unforgettable.
10. Pepsiman (1999)
An advertisement-turned-game: dash through cityscapes delivering Pepsi, dodging chaos, with a glittering metallic silhouette delivering soda salvation. It’s wonderfully absurd, bizarrely mesmerizing.
The Digital Dreamscape Is Open
All of these games live on the edge between nostalgia and unreality. They're artifacts and gateways to a time when software was unique and strange. Thankfully the Internet Archive is their mausoleum and revival chamber all at the same time.
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