Question: what is the most collectible playboy magazine?
Answer: December 1953 – Marilyn Monroe.
March 1980 – Bo Derek. ... 
November 1993 – Jerry Seinfeld and Various Models (Original Cover Photo) ... 
September 2009 – Heidi Montag (Original Cover Photo) ... 
August 1993 – Pamela Anderson and Dan Aykroyd (Original Cover Photo) ...