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.
I was playing the Super Mario RPG remake and thought about how much I want another Goemon game.