Work on the publication consumed much of Hefner's life and marriage.
By the late '50s, , with sales reaching a million copies a month. Hefner and his first wife divorced in 1959 after having had two children, Christie and David.
For those who initially dismissed the magazine as a pornographic publication, logo, depicting the stylized profile of a rabbit wearing a tuxedo bow tie, appeared in the second issue and remained the trademark icon of the brand.
Hefner chose the rabbit for its "humorous sexual connotation" and because the image was "frisky and playful"—an image he fostered in the magazine's articles and cartoons.
Over the years, Hefner's Playboy Enterprises also built hotel resorts, started modeling agencies and operated a number of media endeavors.
Hefner hosted two short-run television series, (1969–70), with guests like Milton Berle and James Brown.
Both programs were weekly talk shows set in a bachelor pad full of Playboy Playmates, who chatted with Hefner and his special guests about various subjects.
And whatever we did, would the keyholders be disappointed? Because it was Playboy, they brought the fantasy with them.This was also 's golden age as ever-increasing circulation allowed Hefner to build a vast enterprise of "private key" clubs that, among other traits, were racially inclusive in a time where segregation was still legally enforced.(A documentary on Hefner that focused on his civil rights activism later received a NAACP Image Award nod.) Hostesses, known as Playboy Bunnies for their scanty outfits made up of rabbit ears and puffy tails, staffed these high-end establishments.To help ensure its success, Hefner had purchased a color photograph of actress Marilyn Monroe in the nude—which had been taken some years earlier—and placed it in the centerfold of the magazine.The first issue quickly sold more than 50,000 copies, and became an instant sensation.He studied at the Chicago Art Institute for a summer before enrolling at the University of Illinois at Urbana-Champaign, where he majored in psychology.