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Start of career.
Hugh Hefner joins the U.S. Army as an infantry clerk and draws cartoons for the Army newspaper. -
College
He grraduated from University of Illinois after just 2 ½ years with a bachelor’s degree in psychology and a double minor in art and creative writing. He had taken on position as assistant personnel manager for the Chicago Cartoon Company. -
An important decision
After failing to sell his ideas for a cartoon strip, Hefner publishes That Toddlin’ Town, a book of cartoons about Chicago. He gets a job at Esquire as a promotion copywriter. He was denied a $5 raise when the publication moved its offices to New York and he decided to stay behind in Chicago to create his own magazine. -
Start of Playboy.
Hugh Hefner collaborates with another copywriter to raise enough money to publish a new Chicago magazine and fails his mission. He starts working for Publisher’s Development Corp. as a newsstand and promotions director and discovers a high demand for for a gentlemen's magazine. -
Success
He raised $8,000 from 45 investors and a $1,000 contribution from his mother to launch Playboy magazine. At first he wanted Stag Party as the title for his magazine but because of the challenge with title trademark infringement, a friend suggested Playboy. Playboy hits newsstands selling 54,175 copies with covergirl Marilyn Monroe setting the bar for future bunnies. -
Raises the Bar
Playboy begins selling 700,000 copies per month. -
More to come
Hugh Hefner decides to open a Playboy club in downtown Chicago. -
Big purchases
Playboy becomes the most influential men’s magazine worldwide in this decade, with circulation numbers at 7 million, dominating other men’s magazines. Hefner purchases a black McDonnell Douglas DC-9-30 naming it the Big Bunny airline jet in which he jets around the world. -
Playboy mansion
Playboy Enterprises goes public, selling 7 million magazine copies every month. The company successfully purchases 23 Playboy Clubs, resorts, hotels and casinos and boasts more than 900,000 members worldwide. He then purchases the famed Playboy Mansion on a five-acre estate in the Holmby Hills area of Los Angeles. -
Trying something new
Hugh Hefner launches reality series called The Girls Next Door, with Kendra Wilkinson, Holly Madison, and Bridget Marquardt. The series airs in more than 150 countries worldwide. Celebrates Playboy’s 50th anniversary with live music, stand-up comedy, and interviews and is featured in a two-hour special on A&E. He attempts to expand with a Playboy version featuring South Asian women and Indian pop culture articles to India but it was rejected.
