In 1960, Playboy had been in publication for 7 years, and Hefner had been cementing his status as a lothario, and an all-round legend. He is pictured here at a Chicago nightclub in 1960 with just a few of his many, many Playboy Bunnies.
113. 1980: Gene Simmons and Cher Share a Creme Puff at Studio 54
Between 1977 and 1980, Studio 54 was the be all and end all of nightclubs. The New York club allegedly earned $7 million in its first year in business. Everyone who was anyone was seen at Studio 54, and here we have Cher and Gene Simmons, in full Kiss cotume, sharing a creme puff. The couple dated for a short period of time when this photo was taken.