For me it's Captain Claw - 2d platformer for PC
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Kid Klown in Crazy Chase (Super NES)
Short and sweet, arcady platformer. Very trial-and-error, though, and the final segment is pure RNG. I don't blame anyone for using save states playing it today.
Mystical Ninja Starring Goemon (Nintendo 64)
Prototyped the 3D action-adventure gameplay model a full year before Zelda: Ocarina of Time did (7 August 1997 vs. 21 November 1998). Wacky Japanese humor, amazing soundtrack, and generally stuck in my mind as THE game of my simpler childhood times.
When Goemon blew that conch and the giant mech appeared I laughed because it was going to be that type of game
Along those lines, Mischief Makers for the N64. A very good side-scrolling platformer, where at one point you play a dodge ball game against a small, helpless cat, and on the next stage you're riding the cat in a fight against a giant tank that you defeat by catching its bullets and throwing them back at it.
Five year old me was completely baffled.
I was playing the Super Mario RPG remake and thought about how much I want another Goemon game.