He plays when hes supposed to be working (5)
I believe the answer is:
actor
'he plays when hes supposed' is the definition.
The answer is a person as well as being a singular noun. This is suggested by the definition.
'to be working' is the wordplay.
I cannot quite see how this works, but
'to' is present in the answer.
This explanation may well be incorrect...
Can you help me to learn more?
(Other definitions for actor that I've seen before include "One taking part" , "One in a play" , "Player - performer" , "For example, Colman" , "Thesp" .)