The Surprising Place Hugh Hefner Worked Before Creating Playboy

Hugh Hefner, founder and editor-in-chief of the controversial and iconic Playboy magazine didn't always live a life surrounded by luxury. As a publisher, he was known to wear silk pajamas all day, surrounded by his Playboy bunnies, the glamorous staff who lived by his side until his death, according to the New York Times. Hefner died of natural causes on September 27, 2017, in his famed Playboy Manson worth $100 million. During his over six-decade career, he changed the cultural conversation around the world about sex, love, and self-expression by starting a publication that offered sophisticated discussion, notes Biography. 

Hefner is often referred to as a "cultural icon" who made history by turning his Playboy brand "into a forum for sexual freedom and progressive politics, advocating for civil rights and free speech," per CNN. Before his $1 million a year salary and living at the Playboy Mansion, Hefner was an average worker holding various creative jobs around his hometown of Chicago with little financial backing to support his dream of running his own magazine one day, according to Fortune.

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.

Before the iconic founder and editor-in-chief of "Playboy" Hugh Hefner could put his vision of placing sexy photoshoots with a sophisticated presentation into a magazine, he needed to find some supporters who were willing to invest in his idea after his failed previous attempts. Although his father didn't donate to his son's vision, Hefner told Fortune (via CNN) his mother and brother contributed a combined $2,000, his "largest financial investments" at the beginning, which landed him with $8,000 total to go forward with his Playboy dream and the soon-to-be-infamous first issue.

Hefner thought of the name "Playboy"' for the publication. He felt it reflected a mixture of high living and sophistication, according to Biography. And with the minimal funds he had raised, Hefner cemented the first edition of the publication, which first hit newsstands in December 1953. The magazine quickly became an instant sensation, with its first issue featuring a colored photograph of actress Marilyn Monroe posing nude, selling more than 50,000 copies. By 1972, nearly two decades after that first issue, Playboy Enterprises would make $12 million in profit and be known as a major corporation. 

Hefner's net worth was estimated by Celebrity Net Worth to be $50 million at the time of his death in 2017. Not bad for a former cartoonist from Chicago.