Look at the start or end of the clue

This is a container clue - look for indicators like 'around', 'holding', 'outside', 'embracing' where one part wraps around another

Break down the clue into definition and wordplay parts

Answer: BOBDYLAN | Wordplay: Whiny singer with boy band playing around Leatherhead (3,5)L[eather] in (BOY BAND)*