Conversation so far:
What can you tell me about Jack's characters?
Benny's comic persona changed over the course of his career.
At some point he developed a miserly persona.
what other Persona did he have?
This stage character was everything that Jack Benny was not: cheap, petty, vain and self-congratulatory.

Question: Did he like the characters that he played?
Self-contained rewrite: Did Jack Benny like the characters that he played?