After working in Chicago for Esquire writing copy, Hugh Hefner quit his job in 1953 and raised around $8,000 to launch the magazine that would eventually become Playboy.
From his Hyde Park kitchen, he wrote the first issue of the magazine on his college Underwood Standard Four Bank Keyboard portable typewriter.
That typewriter is up for auction at Goldin, with a starting bid of $10,000. It previously sold as part of Hefner’s collection for $162,500 in 2018.
Obsessed with Marilyn Monroe, Hefner paid a Chicago calendar company $500 for her nude photos, one of which would end up on the now-famous debut cover.
Monroe was originally paid just $50 for the photo shoot in 1949, never seeing a dime from the magazine. She once reportedly said she “even had to buy a copy of the magazine to see myself in it."
The magazine’s influence on popular culture and the sexual revolution was immense, and remains a key collectors item — especially the first issue featuring Monroe. Copies in excellent condition have fetched more than $70,000.
Will Stern is a reporter and editor for cllct, the premier company for collectible content.