Title of head of household once — Benny, possibly? (7)
I believe the answer is:
goodman
I believe this clue is a double definition.
'title of head of household once' is the first definition.
(archaic term for the male head of a household)
'benny possibly?' is the second definition.
(musician Benny Goodman is an example)
(Other definitions for goodman that I've seen before include "Benny ___ , 'King of Swing'" , "jazz player" , "Jazz musician" .)