Swindler chosen to play Hooray Henry? (8,6)
I believe the answer is:
chinless wonder
'hooray henry?' is the definition.
(both can informally mean an upper-class person)
'swindler chosen to play' is the wordplay.
'to play' indicates anagramming the letters.
'swindler'+'chosen'='swindlerchosen'
'swindlerchosen' is an anagram of 'CHINLESS WONDER'.
(Other definitions for chinless wonder that I've seen before include "Weak character" , "ineffectual toff" , "One ineffectual" , "unexceptional toff" , "weak swell" .)