ass-back·wards
/ˌasˈbakwərdz/
adverb
in a manner contrary to what is usual, expected, or logical.
"I never did like to do anything simple when I could do it ass-backwards"
adjective
contrary to what is usual, expected, or logical.
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ludicrously disordered : showing an arrangement grotesquely counter to the usual or workable. incompetents doing their work in an ass-backward way.
The earliest known use of the word ass-backwards is in the 1930s. OED's earliest evidence for ass-backwards is from 1934, in the writing ...
Ass Backwards
2013 ‧ Comedy/Adventure ‧ 1h 30m
4.3/10 · IMDb
27% · Rotten Tomatoes
Mishaps and calamities befall two best friends (June Diane Raphael, Casey Wilson) who are on their way back to their hometown for a children's beauty-pageant reunion.
Rating
(124)
Two best friends, Kate and Chloe, met when they both came dead last in their hometown pageant. All grown up, they hit the road on a cross country trip back ...
(idiomatic, colloquial) Hopelessly misguided; contrary to what is normal, expected, or logical; having taken the utterly wrong choice.
Dec 3, 2023 · I don't know for definite, but it reminds me of the phrase arse over tit - basically to fall over. Probably just colloquial slang for messing up ...