slang used by Irish people and some English that is usually used to indicate someone is broke.
not sure where it originated...but, as a wild guess it might have something to do with "bob" also being the nickname of a coin in old irish currency (pre-metric) coupled with the fact that Bob Dylan looks permanently skint. (great singer/songwriter though!)
Also, "bob dylans" ryhmes with "shillings". A shilling was the equivalent of a new 5pence coing in new money.
So it could also be ryhming slang for shillings.
Seán: "are you heading out for a few pints, Michael?"
Michael: "Sorry I can't, unless u can sort me with some bob dylans until Friday."
"can you spare some bob dylans, Michael? the dealers outside and he's going to put my balls where my lungs are if I don't sort him out".
Prices shown in USD.
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