Data and C-3P0. Wrestling would get boring very fast, and Boba Fett doesn't speak much so it wouldn't be that interesting.
Would you rather see Trip in a detective story or Picard in a Western?
I've actually seen Picard in a Western, and it was epic. So my vote's with Old Baldy, although watching Trip get nut-punched by Professor Moriarty would definitely carry some entertainment value.
Would you rather have a Gorn or a Klingon as ship's counselor?