This was uttered by the green horned demon Lorne on the t.v. show Angel. He was commenting on how things were even more chaotic than usual. This is a mashup of “head over heels” (completely, thoroughly) and “ass over teacups” (flipped upside down). This is an interesting mix, as “head over heels” literally means flipped upside down, or “ass over teacups”. Also, the word “over” is used in both expressions, contributing to the mixup. A big thanks to John Kooser who heard this one and reported it immediately.