Smashed and penniless (5)
I believe the answer is:
broke
This clue is a double definition.
'smashed' is the first definition.
(I've seen this before)
'penniless' is the second definition.
(I've seen this in another clue)
'and' acts as a link.
(Other definitions for broke that I've seen before include "See 19" , "Completely out of money" , "Ordinal number" , "Impecunious" , "Moneyless" .)