[emptybits]

I have loved this word since I first heard it. I assumed it evolved out of the common expressions: "get your head out of your ass" or "he's got his head up his ass".

To me, this evokes an image of wearing one's ass as a hat. I love the ridiculousness of picturing that.

[datavirtue]

Yeah, it made its way into my quiver by hanging around slashdot for years.

[sethammons]

That's where I learned it too :)

[ChickeNES]

There and Fark for me

[TylerE]

I’ve always taken it had being derived from this 1976 movie line: https://movie-sounds.org/western-movie-quotes/quotes-with-so...

[JKCalhoun]

If I had to guess: it is a version of asshole you might be able to say in front of your mother.