1950 Hef gets work as an advertising copywriter for the Carson, Pirie, Scott department store. Salary: $40 a week.

1951 In January Hef lands a job as a promotion copywriter at Esquire earning $60 a week. When the magazine relocates to New York, Hef's request for a $5 raise is declined, and he stays behind to found his own magazine.

1952 Hef tries to save money while working as the newsstand promotion director of Publishers Development Corporation. Hef and Millie have their first child, Christie.

1953 At the age of 27, Hef produces the first issue of Playboy magazine on a kitchen table in his South Side apartment, featuring the infamous nude of Marilyn Monroe as "Sweetheart of the Month."

1954 With the second issue, published in January, Hef introduces the "Playmate of the Month" with Miss January Margie Harrison and the Rabbit Head, designed by Art Paul, on the cover.

1955 Hef and Millie have their second child, David.

1956 After being denied his application for a second-class mailing permit, Hef goes to court. He wins, securing Playboy the mailing privileges other publications enjoy.

1957 Hef hires renowned Esquire magazine artist Alberto Vargas. The Vargas girl appears in Playboy exclusively from 1960 to 1978.

1959 Cynthia Maddox, who would become Hef's girlfriend and the magazine's Assistant Cartoon Editor, begins as a receptionist at Playboy.

1959 Hef makes his first pilgrimage to the South of France, where he hopes to meet Brigitte Bardot at the Cannes Film Festival. She's not there. But, he returns, more inspired than ever to live out his dreams.

1959 Hef introduces the Playboy Jazz Festival at Chicago Stadium. The three-day festival in August sells out and features Miles Davis, Count Basie, Ella Fitzgerald, Duke Ellington and almost every other jazz star in the country.

1959 Playboy's Penthouse, a popular hour-long weekly television variety show hosted by Hef, premieres in October.

1959 Hef purchases the Playboy Mansion on Chicago's Gold Coast in December.