Hugh Hefner: A Life of Firsts

Hugh Hefner's lifestyle has forever changed American pop culture. From small publication to full blown international brand, Hefner became one of the most famous entrepreneurs of our time.

But the man who grew up to be a magazine magnate and famous playboy came from humble beginnings in the Midwest. It was that background that informed and inspired his business and personal decisions.

Here, we take a look at some of the "firsts" in Hefner's life — the moments that have shaped the man and the iconic Playboy brand.

Posted: 07 October 2010
By: Constance Parten

Hugh Hefner met Mildred Williams at a party shortly after graduating from high school and the two hit it off immediately. They began dating, but their romance was cut short when Hefner had to leave for the army in 1944.

The two were able to keep in touch by writing each other letters. When Hefner returned from the army in 1946, he joined Millie at the University of Illinois. Hefner graduated in 1949 and the couple wed soon after.

But before they married, Mildred revealed she had an affair. The wedding went forward, but the shock of the betrayal haunted Hefner.

"That betrayal really shaped his view of women," Steven Watts, author of Hefner biography Mr. Playboy, said. "He loves them. He adores them, but there's that little edge of sort of keeping an eye open at the same time."

Not content with the direction his life was taking, Hugh Hefner decided to embark on his own creative endeavors. In 1951, Hefner published That Toddlin Town, which featured a series of risqué cartoons that poked fun at the social scene around the streets of Chicago.

The book achieved mediocre success making him a minor celebrity in Chicago and earning him a couple of thousand dollars profit. Little did Hefner know that in less than two years, he would create a magazine that would change everything.

Hefner’s first child, Christie, was born Nov. 8, 1952. Thirty years later, all grown up, Hefner’s little girl was taking charge of Playboy Enterprises, Inc. as President. She led the company into the digital age, taking the magazine to the Web as the first national magazine on the Internet, according to Forbes and other media reports.

"I sort of stepped in in the early '80s to try and put the company back on sound financial footing and get rid of the businesses that weren't working — the record company, and the book publishing business, and the modeling agency, and the resorts."

When Playboy premiered in January 1953, Marilyn Monroe was featured as the magazines first “Sweetheart of the Month.”  But by the next issue, Hefner decided to rename the title to the now widely recognized “Playmate of the Month.”

In the beginning, Hefner sought out the girl next-door type for his centerfolds, choosing girls who appeared wholesome and natural. The “Playmate of the Month” would soon become the central figure of each issue and the main attraction to many of its consumers. Over the decades, the “Playmate of the Month” would expand to include celebrities, models, singers and athletes.

Monroe wasn't Hefner's first choice for the first magazine, however. His initial idea was a little more high-tech ...

In June 2010, Playboy featured Hope Dworaczyk as its first-ever 3-D centerfold. Though it was a first, it was one of the oldest ideas Hefner had for the magazine.

"What's really wild for me, is for the very first issue when I started Playboy, I was going to put 3-D glasses in it and a pictorial — a nude pictorial," Hefner said. But he couldn't find the money for the glasses, so instead he went with the now famous Marilyn Monroe calendar photos for the first issue.

In the late 1950s, Hefner went through a major life change, coming out from behind the desk at Playboy and starting to live the life he'd been promoting in the magazine. He divorced his wife, bought a sports car, and donned a new wardrobe. And in 1959, he bought the original Playboy mansion on Chicago’s Gold Coast in for around $400,000.

The mansion soon became known for its outlandish parties, celebrity guests and beautiful women becoming the epicenter for all things mischievous in the windy city. It was even equipped with a brass-plated sign on a door that read: Si Non Oscillas, Noli Tintinnare. Translation: If you don't swing, don't ring.

But by the mid-1970s, Hefner had outgrown Chicago, so he packed up and built a new one in the Holmby Hills area of Los Angeles.

Hugh Hefner wanted every aspect of Playboy Magazine to reflect the lifestyle brand that he was trying to create for his audience. Many advertisers were put off by the risqué publication and didn’t want to be identified with it, but Hefner wanted only products that reinforced the lifestyle brand he was creating.

He declined 75 percent of advertisers that wanted to place what he considered “tawdry ads,” in the magazine. It was a bold move for a young publication, but it eventually paid off.

Two years after the first issue of Playboy Magazine hit the newsstands, Hefner landed his first major advertising account with Springmaid sheets.

Marilyn Cole started out working as a bunny at the Playboy Casino in London. The tall beauty soon caught the eye of Victor Lownes, who was in charge of operations at the casino.

Lownes sent Hefner some test shots of Cole and soon after she was whisked out to Chicago to shoot a pictorial for the magazine. Marilyn Cole would eventually become Miss January 1972 and Playmate of the year in 1973.

The pictorial also made her the first completely nude and exposed Playmate. The decision to publish the photo was a direct result of the magazine's new competitor, Penthouse.

"There was something called the Pubic Wars with Guccione and Penthouse and his circulation was rising and I think Playboy and Hefner had to face that," Lownes said.

And before the war was over, Playboy's poses would get more and more provocative.

The first Playboy Club opened in downtown Chicago on February 29, 1960, allowing its patrons to experience the Playboy lifestyle that existed between the pages of the magazine.

Bunnies, cocktails and live entertainment were all part of the allure. The club was an instant success and soon others began opening all around the world.

"The world of Playboy became a sort of concept outside of the magazine itself, and Playboy Clubs were the first big step into the outside world," said former Playboy executive and Hefner confidant Victor Lownes.

The number of Playboy Clubs would grow to more than 22 over the next decade. But by the mid 1970s, the club life was coming to an end.

Premieres Tuesday, October 12th 9p | 1a ET

• About the Show
• Video: Girls Next Door
• Video: Playboy Playmates