Crown and Anchor content to leave a pint every now and then on the counter (5)
I believe the answer is:
tiara
'crown' is the definition.
(tiara is a type of crown)
'anchor content to leave a pint every now and then on the counter' is the wordplay.
'content to leave' suggests removing the centre (the contents of the word are removed).
'every now and then' means one should take alternating letters (letters selected at regular intervals).
'on the counter' shows that the letters should be reversed in order (counter can mean in the opposite direction).
'anchor' with its centre removed is 'ar'.
The alternate letters of 'pint' are 'it'.
'ar'+'a'+'it'='arait'
'arait' in reverse letter order is 'TIARA'.
'and' acts as a link.
(Other definitions for tiara that I've seen before include "Type of diadem" , "Half-crown?" , "Women's head ornament" , "Half a crown!" , "Jewelled headband" .)