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Hugh Hefner: Trivia About America's Most Famous Playboy.

Updated on September 21, 2018
Timothy Anderson profile image

Tim Anderson is a freelance writer/researcher with articles published in The Saturday Evening Post, Playboy magazine, TV Guide, and others.

Hugh Hefner and Marilyn Monroe never met in real life.  But their names will be linked together for eternity, just as their burial sites are today.
Hugh Hefner and Marilyn Monroe never met in real life. But their names will be linked together for eternity, just as their burial sites are today.

WW II Army Vet

Hugh Marston Hefner served in the U.S. Army during World War II.

He served from 1944 to 1946, writing for a military newspaper, and was honorably discharged in 1946.

While he was in the service, his girlfriend back home -- Millie Williams -- had an affair which reportedly was devastating to him. None-the-less, the couple married in 1949 with the agreement that because of her cheating, he could have sex outside their marriage.

The marriage would produce two children, Christie and David, but ended in divorce in 1959.

Hugh Hefner and his first wife, Millie Williams.  She was the first lover he ever had and he was distraught when he learned she'd been unfaithful to him.
Hugh Hefner and his first wife, Millie Williams. She was the first lover he ever had and he was distraught when he learned she'd been unfaithful to him.

"Picasso had his pink period and his blue period. I am in my blonde period right now."

— Hugh M. Hefner
In 1963 Hefner was arrested for "promoting obscene literature" by the Chicago Police Department after Playboy magazine published nude photos of actress Jayne Mansfield.  The trial ended in a hung jury.
In 1963 Hefner was arrested for "promoting obscene literature" by the Chicago Police Department after Playboy magazine published nude photos of actress Jayne Mansfield. The trial ended in a hung jury.

BRFs -- Best Roommates Forever

The woman who will always be associated with Playboy magazine is the publication's first centerfold, sex symbol Marilyn Monroe.

Hefner bought the rights to reproduce her famous nude calendar pose and made her fame even greater when he put it in his first issue of Playboy in 1953.

Ironically, Hefner never met Marilyn Monroe, but in 1992 he purchased the burial vault next to hers at Westwood Memorial Park in Los Angeles for $75,000. It is in the "Corridor of Memories," and is Crypt #24.

Friends say Hefner, an agnostic who doubts there's an afterlife, rarely talked about death.

Hef's final resting place will be in the burial vault next to the woman he helped make famous: Marilyn Monroe.
Hef's final resting place will be in the burial vault next to the woman he helped make famous: Marilyn Monroe.

Hef the Would-Be Cartoonist!

As a child, Hugh loved to draw. He loved to write short stories and then illustrate them with his own drawings. By the time he reached high school, he was enjoying himself so much he actually created an autobiographical comic book he called "School Daze."

Later, when serving in the Army from 1944 to 1946 he became a huge fan of Terry and the Pirates illustrator Milton Caniff. Caniff had been publishing a cartoon strip in the "Stars & Stripes" military newspaper called Male Call, and Hefner loved his style.

So in the summer of 1953 as he was preparing the first issue of Playboy, Hefner wrote to the famous cartoonist and convinced him to allow some Caniff cartoon reprints to be used in the magazine. Caniff agreed, and the cartoons appeared in the second issue of Playboy.

Growing up, Hefner had always wanted to be a cartoonist, but after the success of Playboy magazine, he comfortably settled in to the "editor-in-chief's" chair and went on to publish the work of some of the greatest cartoonists in America.

Hugh Hefner and former U.S. President George W. Bush are distant cousins.
Hugh Hefner and former U.S. President George W. Bush are distant cousins.

Hef and George W.--Keeping It The Family

Hugh Hefner was a descendent of a puritan -- William Bradford -- who came to America on the Mayflower.

Furthermore, he's a ninth cousin to former U.S. President George W. Bush, and an eighth cousin to U.S. Secretary of State and former U.S. Senator, and Secretary of State, John Kerry.

Hugh M. Heffner.  America's official "Playboy."
Hugh M. Heffner. America's official "Playboy."

Left Standing at the Alter

Hefner is on the list of men who were left standing at the alter.

After dating model Crystal Williams following the end of his seven-year relationship with Holly Madison, Hef became engaged to Harris and after her acceptance, began to make plans for a July 2011 wedding. It was going to be one of the biggest and most publicized nuptials in Hollywood.

And, after all, with the dozens and dozens of girlfriends he'd had over the decades, the title "Hugh Hefner wife" wasn't seen very often in his biographies.

But just days before the wedding, and with her photo on the July 2011 issue of Playboy trumpeting the nuptials, Harris got cold feet and bolted. Hefner was stunned, but told her to keep the Bentley he'd gifted her with, and also her engagement ring.

After a cooling-off period, the would-be bride reconsidered and the pair began dating again, and on New Year's Eve 2012, the 86-year-old Hefner and his 26-year-old bride were married in small private ceremony at the Playboy Mansion.

Hef with two of his girlfriends -- Kendra Wilkinson and Bridget Marquardt -- before he married model Crystal Harris in 2012.
Hef with two of his girlfriends -- Kendra Wilkinson and Bridget Marquardt -- before he married model Crystal Harris in 2012.
Hugh Hefner circa 1950s as he began to build the Playboy empire.
Hugh Hefner circa 1950s as he began to build the Playboy empire.

Hef's Childhood Bunny Blankie...

After marrying in 1949, Hugh Hefner had several jobs (including a job writing for "Child Life" magazine) before settling in at Esquire magazine's Chicago headquarters where he worked as a copywriter. It was here where he continued to hone his writing skills, and became familiar with the artwork of artists like Alberto Vargas and George Petty.

But in January 1952, after Esquire planned to relocate to New York City, Hefner asked for, and was refused, a $5-a-week raise.

Feeling unwanted, the young soon-to-be-father left Esquire and after some thought, decided to publish a men's magazine he planned to call "Stag Party." However, realizing there could be legal issues with another magazine on the market called "Stag," Hefner went with his second choice, which was Playboy. He even chose the icon he wanted associated with his new publishing venture: a bunny. It seems as a child he had a blanket covered with little bunnies, and it was a possession he truly cherished.

He ponied up $600 of his own money, and then raised $8,000 from nearly 50 investors, one-quarter of it coming from his mother and brother who contributed $2,000. His mother would later say she wasn't overly thrilled at the expected content of the magazine, but contributed because she believed in, and wanted to help her son succeed.

In December 1953 the first issue of Playboy hit the stands. It didn't have a printed date on the cover because Hefner wasn't sure when, or if there'd be a second issue. But his hard work and planning paid off: more than 50,000 copies were sold and Playboy magazine would soon become an American publishing icon, and Hugh's bunny face icon would soon become one of the most recognized corporate symbols around the world.

Hefner Has a Silicone Double

While Hefner's personality has been described as anything but stiff, the fact remains he has his very own full-size likeness at the Madame Tussaud's Interactive Wax Museum at the Venetian Casino in Las Vegas.

But, with a wink to Hef's work in the adult entertainment area, unlike the other models on display, Hefner's is made out of silicone and not the standard wax used for the other celebrity likenesses.

And, no doubt Mr. Playboy would chuckle today if he knew a "Hugh Hefner costume" is always popular around Halloween!

Hef's Bio in Five Minutes!

Guinness World Record Holder

One can imagine all sorts of records Hugh Hefner might be tagged for in the Guinness Book of World Records, but the two records he's noted for may surprise you.

He is listed as having the longest career with the same magazine as the editor-in-chief (nearly 60 years), and he has the largest known personal scrapbook collection of anyone living today. Hef's hobby of filling scrapbooks with clippings and photos from his long career and personal life has filled nearly 2,700 scrapbooks which are carefully stored in the Playboy Mansion.

© 2016 Tim Anderson

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