I have no doubt funny or odd juxtapositions of songs happen several times daily to just about everyone on these forums... Either clashing songs or eerily appropriate ones... Comes with the territory of being able to shuffle one's entire music collection!
My favorite one from recent memory was "California Dreamin'" by the Mamas and the Papas, immediately followed by "California Dreamin'" by Me First and the Gimme Gimmes. Same song, but a clash in styles that cannot be described unless you've heard them.
I'm sure people here will have other funny ones to contribute.