In 1959, Hugh Hefner bought the original Playboy Mansion in Chicago, Illinois. By then, Shel Silverstein was part of Hefner’s inner circle. Having previously described himself as less than successful with women, Silverstein was suddenly a popular and sought-after man. According to writer Lisa Rogak, author of the unauthorized 2007 biography “A Boy Named Shel: The Life and Times of Shel Silverstein,” “For the first time in his life, women began to look his way, to flock to him.” Silverstein’s friend and collaborator Rik Elswit of the rock band Dr. Hook noted, “Shel was not handsome … Maybe it was his eyes; they would twinkle and pierce simultaneously, giving you the impression that he knew something you didn’t.”
Silverstein could be found living at the mansion for weeks and months at a time, often lurking in the background and waiting for other revelers to come to him. He enjoyed meeting creative, interesting people and wrote poems for several of his children’s books while staying at the mansion. In a 2001 article for The New York Times, playwright David Mamet wrote that Silverstein was considered a “demigod” in Chicago; among his many attributes, “He was Hugh Hefner’s sidekick, he was the great cartoonist, he lived with Hef at the Playboy Mansion, in a riot of delight.”
Silverstein died in 1999 at his home in Key West, Florida. He was 67. Per his New York Times obituary, his books sold a total of 14 million copies during his lifetime.