Cheerless penny raise (5)
I believe the answer is:
drear
'cheerless' is the definition.
(similar in meaning)
'penny raise' is the wordplay.
'penny' becomes 'd' (pre-decimalisation abbreviation for penny).
'raise' becomes 'rear' (as in rearing children).
'd'+'rear'='DREAR'
(Other definitions for drear that I've seen before include "Literarily gloomy" , "Morose" , "Gloomy and cheerless" , "miserable" , "grave" .)