Original degenerate, playboy buccaneer (5)
I believe the answer is:
drake
'buccaneer' is the definition.
(Sir Francis Drake)
'original degenerate playboy' is the wordplay.
'original' indicates taking the first letters.
'playboy' becomes 'rake' (old-fashioned term for a womanising man).
The first letter of 'degenerate' is 'd'.
'd'+'rake'='DRAKE'
(Other definitions for drake that I've seen before include "Hoe user" , "Male water-bird" , "First English captain to sail round the world" , "Elizabethan sailor" , "Plymouth bowler" .)