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Thank you for replying, smouse and bookwormer, and it would appear that you have "cracked it" bookwormer.
I changed 102 from Harold to Caesar or Centurion, when my knowledgable wife assured me that a Roman or Greek was depicted - not anyone English or Danish.
I had Jolly Roger for 106, but your Skull and Crossbones is apt, and gets rid of the awkward letter J.
I thought 108 was George Clooney, but I see where you are coming from with Des O'Connor.
Once again, many thanks.