Show boss maybe a strange game, foolishly (5,7)
I believe the answer is:
stage manager
'show boss maybe' is the definition.
(someone in charge of a show)
'a strange game foolishly' is the wordplay.
'foolishly' indicates an anagram.
'a'+'strange'+'game'='astrangegame'
'astrangegame' is an anagram of 'STAGE-MANAGER'.
(Other definitions for stage manager that I've seen before include "Chief theatre technician" , "Supervisor in theatrical production" , "State of NW USA" , "One in charge of theatre production" , "Play supervisor" .)