Was the lead singer a big stockholder? (7)
I believe the answer is:
rancher
'a big stockholder?' is the definition.
The answer and definition can be both people as well as being singular nouns.
Perhaps there's an association between them I don't understand?
'was the lead singer' is the wordplay.
'was the lead' becomes 'ran' (I am not sure about this - if you are sure you should believe this answer much more).
'singer' becomes 'cher' (American singer).
'ran'+'cher'='RANCHER'
Can you help me to learn more?
(Other definitions for rancher that I've seen before include "Cattle baron" , "A cowboy" , "US cattle breeder" , "Hacienda owner" , "US cattle farmer" .)