Likeness to rap artist regularly is awkward (8)
I believe the answer is:
portrait
'likeness' is the definition.
(portrait is a kind of likeness)
'to rap artist regularly is awkward' is the wordplay.
'regularly' means one should take alternating letters (regularly take one letter, leave next etc.).
'is awkward' indicates an anagram.
The alternating letters of 'artist' are 'rit'.
'to'+'rap'+'rit'='toraprit'
'toraprit' is an anagram of 'PORTRAIT'.
(Other definitions for portrait that I've seen before include "Type of painting" , "characteristic depiction" , "Head/shoulders painting" , "Painted likeness of a person" , "Image of a person" .)