29. Hugh Hefner & Playboy Playmates
We’ll show you the luckiest guy in the world if you can count the number of Playboy Playmates in the photo. On his left and right are nine, yes nine, Hugh Hefner Playboy Playmates in devilish disguises.
Whenever we’re trying to come up with names for all of the costumes we see here, the words “sexy” and “naughty” keep coming up in our heads. This photograph was taken outside of the Las Palmas nightclub in Hollywood in 2001, when Hugh Hefner was dating a number of different women at the same time, according to the photographer.