Ooh! Glad to see the Cho Aniki series is still alive and kicking.
But yeah, like John-to-the-John Sandoval said, Japanese game developers have been doing this kind of thing since, well, they first started making games. For historical reference, see Parodius (1988)
, Trio the Punch (1990)
, PuLiRuLa (1991)
, the aforementioned Cho Aniki (1992)
, etc etc. Give me an hour or so and I could probably wrangle up a few dozen or so games that fit your criteria. And those are just the games
; mentioning all the weird anime, manga, live-action TV series and so on would take a very long time.
Fortunately for us, this culture of perpetual weirdness/surrealism is starting to make its way to the western world, with shows like Tim and Eric and whatever crap Cartoon Network is throwing at us nowadays proving that weird is a viable good. So it's very likely that it won't be long before game companies start capitalizing on this culture shift.
Also, Cactus has been doing it to it for years now, and he's like one of the freakin' figureheads of the indie scene!