Chicago shaped Playboy in ways I didn’t realize at the time. New York City seemed a world away from the rest of America, sophisticated and socially advanced, detached from the remainder of the country. Chicago stood as the most significant representation of true, post-war America. The high-rises and subways brimmed with urban men who returned to the city after their experiences abroad and found themselves receptive to ideas that challenged their socially conservative surroundings.
Interested in more than work and domestic security, longing for sexual adventure and enjoying the postwar financial boom, these men looked to spurn the restrictions of puritanical convention in favor of life as a single, city-bred male with a bachelor apartment and a proper martini. I counted myself among them. Playboy’s success proved I wasn’t alone.
The magazine’s success was really unprecedented, and beyond my wildest dreams. We moved into our first offices on the North Side on Superior Street across from Holy Name Cathedral. Our subsequent prosperity allowed me to indulge my fantasies at the Playboy Mansion at 1340 N. State Parkway on the magnificent Gold Coast. We hosted the first Playboy Jazz Festival in 1959 at the Chicago Stadium to celebrate our fifth anniversary. In February 1960 we opened the first Playboy Club on Walton Street. By 1965 we had relocated to the iconic Palmolive building on Michigan Avenue and emblazoned the front with nine-foot illuminated letters spelling out Playboy. The association between Chicago and Playboy became so strong that a letter from a reader once arrived at our offices having traveled the entire U.S. postal system while addressed with only the bunny logo. By the mid-1970s, I moved to Los Angeles, the land where my dreams had come from, but Chicago remained the company’s base, headquartered in the Lake Shore Drive offices we’ve occupied since 1989.
Now, after nearly 60 years, the Playboy offices in Chicago have closed as we consolidate our operations in Los Angeles. It is bittersweet to see Playboy leave the city I love.
Earlier this year, Playboy announced the company was moving their entire operations from Chicago to Los Angeles on April 30. The magazine was founded in Hefner’s hometown of Chicago in 1953.