Cheap fool entertains old boy (3-3)
I believe the answer is:
two-bit
'cheap' is the definition.
(two-bit can mean worthless or poor-quality)
'fool entertains old boy' is the wordplay.
'fool' becomes 'twit' (both can mean a stupid person).
'entertains' is an insertion indicator.
'old boy' becomes 'OB' (abbreviation for a private school 'old boy').
'twit' going around 'ob' is 'TWO-BIT'.
(Other definitions for two-bit that I've seen before include "Inferior - cheap" , "Cheap - insignificant" , "Paltry" , "Cheap (US colloq.)" , "Cheap, worthless (US)" .)