Was a writer for a military newspaper in the U.S. Army
Worked as a copywriter for <i>Esquire</i> magazine; left in 1952 after being denied a $5 raise
Briefly worked as a circulation manager for <i>Children's Activities</i> magazine
Published the first issue of <i>Playboy</i> magazine, featuring Marilyn Monroe on the cover
Organized the first Playboy Jazz Festival at the Chicago Stadium
Hosted the popular syndicated television show "Playboy's Penthouse"
Opened the first Playboy Club on the North Side of Chicago, featuring its waitresses in the now famous 'Bunny' costumes
Returned to the airwaves to host the syndicated show "Playboy After Dark"
Took his company Playboy Enterprises public
Produced Roman Polanski's adaptation of "Macbeth" and the Monty Python film "And Now for Something Completely Different"
Relocated the Playboy offices to a sprawling mansion in Holmby Hills, which came to be known as 'The Playboy Mansion'
Received a star on the Hollywood Walk of Fame after he championed the reconstruction of the Hollywood sign
Profiled in a two-hour special, "Hugh Hefner: American Playboy," as part of A&E's prestigious Biography series
His girlfriends and his life became the focus of the E! reality series "The Girls Next Door"
Partnered with Palms Casino Resort and the Nine Group to develop a Playboy themed nightclub, casino and sky villa located in the Palms Casino Resort in Las Vegas