Kind of a primitive example, but in the old text-adventure Planetfall you had a robot sidekick named Floyd who, when you saved the game would occasionally comment, "oh boy, are we going to do something dangerous now?"
The one I always dreaded was "Wonderful Christmastime" by Paul McCartney. The song already has a ton of weird reverb in it, then to hear it echoing around the mall... Just creepy.
Kind of a primitive example, but in the old text-adventure Planetfall you had a robot sidekick named Floyd who, when you saved the game would occasionally comment, "oh boy, are we going to do something dangerous now?"