Q: Which woman has appeared the most number of times on the cover of Playboy magazine?
A: The holder of the record for having appeared the most often on the cover of Hugh Hefner's magazine is none other than the Baywatch babe Pamela Anderson who has been on it twelve (12) times.
Her career in Playboy spanned between the years 1989 and 2007. She was chosen as a Playmate of the Month in February 1990.