I'll start. "Rue" as in, "you'll rue the day" I'm not really sure how you would go about "ruing" anything at all, never mind a concept. Love the word though.
Bobble. Don't really know why, it's just a word that makes me smile. I remember a match report saying "the pitch was as bobbly as a gypsy's jumper" obviously in less pc days.
Cahoots - no surprise there then! If I opened another bar, it would be, Cahoots - where everyone knows your game. Coat, door, gone.
lugubrious - just like the sound of it as a word. Which even though it's to be sad and quite dismal. All city fans can associate with at some point or other.
Clarts and Bumbailiff. As a kid remember both were contained in a little street ditty which went as follows. Way down in cellarole where muck clarts on winders When we've no coal we start burning cinders If bumbailiffs come they'll never find us Way down in cellarole where muck clarts on winders. Anybody remember other verses?
Omphaloskepsis. I drop this word into reports now and then, just to see if anyone is paying attention, for example "After much ophaloskepsis, the issue was tabled until next month."
antidisestablishmentarianism Never 100% sure what it means, something about about against someone who's against the church?