Before creating one of the most popular adult magazines in the country, Hugh Hefner found himself in a variety of careers in his early 20s, ranging from working in a box manufacturer to churning out ad copy for a department store, according to the New York Times. In 1951, running around his hometown of Chicago, Hefner quit his department store gig and went to work for the men's magazine Esquire. That publication relocated to New York shortly after the future Playboy founder began working there as a copywriter. After being denied a five-dollar raise on his $60-a-week salary to move across the country and continue working with Esquire, Hefner chose to stay in the Windy City and establish a new, trendier magazine, according to the Chicago Tribune.
That same year, 1951, Hefner's first attempt to create his own Chicago-based magazine was deemed unsuccessful. He picked up a position at a children's magazine as a circulation director. Amid these wholesome surroundings, Hefner learned the details of the publishing world and started making his own, decidedly less family-friendly plans. One year later, he would first announce his plan to start the iconic "Playboy" magazine. But first, he needed to find the financial backing to make this risqué dream a reality.
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