Whale of a show, initially? (5)
I believe the answer is:
pilot
'whale' is the definition.
(pilot whale is a kind of whale)
I cannot understand how the rest of the clue works.
Can you help me to learn more?
(Other definitions for pilot that I've seen before include "Plane flier" , "-- Whale; -- light" , "One who brings a vessel into port" , "Flier or helmsman" , "Navigator" .)