Typhoon Thompson

A shoot-'em-up game by Dan Gorlin

Wikipedia: Typhoon_Thompson

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Commentary

Quite possibly the cutest game ever.

Not actually a shoot-'em-up, as the author, Dan Gorlin, pointed out in his interview for Halcyon Days:

I like it because it's unique, the gameplay is simple but infinitely variable, and for me the characters really come to life. Some people mistook it for a shooter at the time, but it's really more like a game of Blitzkrieg Chess. If you just start blasting you lose immediately. Each kind of enemy has moves it can make, and the player has his moves, but things never happen the same way twice. It's not high concept in the way that "Choplifter" is, but rather a kind of art piece.