When the 'Playboy' created history and joined his cover girls

More than a month after his passing, Hugh Hefner has made Playboy history by being the only man to ever appear solo on its cover. The November-December edition features Hefner when he was 39 years old. Hefner died at the age of 91.

By making news with this edition, the magazine’s founder joins the ranks of other women who drew attention to their Playboy covers, most often controversially:

Marilyn Monroe

Playboy made its first splash featuring Marilyn Monroe in 1953. Marilyn was the centrefold of the first issue, although the nude image was actually taken for a calendar. Hugh credited the inclusion of the naked picture of Monroe for making the magazine such a success, with the issue completely selling out. The photo, on a red velvet background, caused controversy in the early years of Monroe’s career, forcing the star to admit that she had posed for the photos only because she needed to pay her rent.

Jessica Alba


(Image: AFP)

The actress was chosen as the publication’s ‘Sex Star of the Year’ for its March 2006 issue, but didn’t fancy being on the cover, so Playboy used a bikini-clad photo of her from a movie poster. She released a statement and filed a lawsuit against the magazine saying that it had “violated my personal rights” and “blatantly misled the public” into thinking she had given her consent to appear on the cover. Hefner managed to calm things down when he donated some cash to two charities of her choice.

Holly Madison

The former Playboy bunny and Hefner’s ‘number one girlfriend’ opened up a can of worms when she lifted the lid on what really goes on in the Playboy Mansion in her 2015 memoir. She spoke about the blatant drug and sexual abuse in the mansion and her bout of depression. “Prior to moving into the Mansion, I’d been a fairly confident person, but it didn’t take long for my self-worth to crumble,’’ Holly wrote in the extract.


Hugh Hefner has made Playboy history by being the only man to ever appear solo on its cover. The November-December edition features Hefner when he was 39 years old.

Jayne Mansfield

One of the earliest playmates for the magazine, Mansfield appeared on its covers for several issues in ‘50s and ‘60s, either topless or in titillating outfits, which landed both Hefner and Mansfield in trouble. While Mansfield’s estranged husband Paul sought custody of their daughter, alleging that Jayne was an unfit mother because she appeared nude in Playboy, Hefner faced obscenity charges in the Chicago city court, his first.

Crystal Hefner

Model, singer and DJ Crystal Hefner became the Playboy runaway bride after leaving Hugh just five days before their scheduled June 2011 wedding. The pair reconciled and married the following year but at the time, in anticipation of the nuptials, a special edition featuring Crystal on the cover had to be rebranded with a sticker, causing outrage over Hefner’s ‘lack of respect for marriage’.