First there was Rube Goldberg who brought us "devices that are exceedingly complex and perform very simple tasks in a very indirect and convoluted way."
Then back in 1987 there was Fischli and Weiss's "The Way Things Go". (sorry no video).
Then there was Pee Wee's Big Adventure and this Family Guy breakfast making machine spoof of it.
Then there was the classic blue ball machine.
Then there was the famous Honda commercial that ripped off Peter Fiscli and David Weiss.