"Tail over teakettle" is one of several similar phrases to describe a tumble or fall. But where/how did this originate? A few web searches give me pages where people use the phrase, and one of the results included a page from Oxford Reference for Green's Dictionary of Slang (but more information requires a subscription). I've been unsuccessful in discovering the etymology of the phrase, though.
Learn English – Origin of “tail over teakettle”
etymologyphrases
Best Answer
According to The Phrase Finder, it is a variation of ass end over teakettle and actually Ngran shows that its usage started a few years later. They are both variations ( other variations exit ) from the well-established expression 'head over heels'. 'Tail is probably used with reference to previous versions which used 'ass or butt.'