Beat outlaw with an awl-tip to show who's boss (3,6)
I believe the answer is:
top banana
'who's boss' is the definition.
'top banana' can be an answer for 'boss' (top banana means a boss or leader). I am not certain of the 'who's' bit.
'beat outlaw with an awl-tip' is the wordplay.
'beat' becomes 'top' (both can mean to defeat).
'outlaw' becomes 'ban' (banning is a kind of outlawing).
'with' says to put letters next to each other.
'awl-tip' becomes 'a' (tip of the word 'awl').
'top'+'ban'+'an'+'a'='TOP BANANA'
'to show' acts as a link.
(Other definitions for top banana that I've seen before include "figurehead?" , "Star comedian" , "Most important person in group (informal)" , "1" , "pick of the bunch?" .)