15 Stunning Starlets Who Posed For Hugh Hefner (And Then Regretted It)

For the first twenty years of print, Playboy was known for its dual-role as a literary magazine and a picture book of nude models. It held the distinction of being both the stomping ground of writers such as John Updike and Joseph Heller and the instigator of the sexual revolution of the 1950s and 1960s.

A picture of Marilyn Monroe adorned the first issue in 1953 and the magazine’s popularity soared; within the first few weeks 53,991 were sold. But by the late 1970s and 80s the magazine’s editorial board knew the literary repartee of the magazine was not what was selling copies. As a consequence, the publication concentrated more on all-out nudity, and celebrity nudity sold even more copies than the unknown; by the late 1990s Playboy was full-on addicted to celebrity photo shoots.

However, as with many of the excesses of the 80s and 90s, Playboy’s lavish labial layouts have since come to an end; in 2015, the magazine announced a stop on its nude photographs of women in an attempt to revitalise its tired and clichéd image. Despite the Playboy of old holding a certain classic reputation, the progress of today’s p--n industry forced it to rebrand (a move which the company’s chief creative officer later admitted “had been a mistake”).

Whether you like it or loathe it, posing for Hugh Hefner’s Rabbit has often been seen as a clever career move. But instead of giving you 15 pictures of the hottest celebs who did just that, let’s flick back through 62 glossy years and find out which of today’s celebrities regretted every minute of their time at the Mansion.


15 Olivia Munn

Perhaps one of the most revealing examples of the type of thumbscrew mentality of glamour photography comes in the form of an excerpt from Olivia Munn’s 2010 book “Suck It, Wonder Woman! The Misadventures of a Hollywood Geek”.

Munn recounts her discomfort when posing for Playboy back in 2009 and surrounded by the “filthy five” which, despite her agreeing to a non-nude shoot, quickly became something altogether more awkward. Afterwards she writes that she had "managed to bury my feelings deep, deep inside…but wanted to break down crying."

According to the 26-year-old American actress and model, the team surrounding her on the day of the shoot did everything they could to have her unclothed, in direct contradiction to what she and her publicist had agreed contractually. Munn tells it with humour but the experience left her, “afraid to speak up and yell at everyone because it would ruin the shoot.”

14 Holly Madison


Life at the Playboy Mansion was beyond anyone’s wildest imagination but for all the wrong reasons, according to Holly Madison, New York Times Bestselling author, model, showgirl, and television personality.

One of Hef’s girls for seven years, Madison quickly realised that her life at Holmby Hills was following just one route – downwards, and in more than one sense, according to her second memoir. The fairy tale existence was marred by the demeaning businessman who, “liked to play favourites to keep everyone on their toes.” And whatever anyone thought of life inside the Mansion, it had a dark side which led Madison to contemplate ending it all. Luckily she didn’t, but she did eventually leave the Playboy Mansion in 2008.

13 Kendra Wilkinson

Kendra Wilkinson, once highly publicized girlfriend of Hugh, was quoted in Life & Style magazine earlier this year as saying that she “hates her 'Playboy' girl label,” but she would be “supportive of her daughter if she wanted to follow in her Playboy footsteps.”

OK, so although the journey for Wilkinson worked out, to a degree, and lifted her from relative obscurity to a household name, the former Bunny has found time to speak out negatively about the venture, leaving us trying to work out what exactly she means by the “label”. Her HuffPost Live interview in 2013 may give us a clue: "If she is in a bad mental place [and has] a bad head on her shoulders and doing it under bad conditions, that's different.”

Wilkinson goes on to say that while she doesn’t regret her decisions, it is important to allow a freedom of choice: “Everybody has to go through little ‘finding out who they are’ stages.”

12 Nicole Deweese


Surely the worst possible outcome of a photoshoot for Hefner’s magazine is some negative publicity, right? Well, think again; Nicole Deweese (AKA Cristy Nicole) who had posed for the glossy in 2010 actually lost her job a few years later as a result.

Miss Deweese was taken on by Townview Magnet High School in Dallas, TX to teach Spanish, but parents argued the availability of her pictures to students in class was distracting. In fact, many went so far as to say her position as teacher was untenable and moved that the 21 year old should be sacked. There was an outpouring of support for the young teacher and some stiff words of justice: “Of course she shouldn’t be fired, nothing she did was illegal.”

But in the end, despite the fact that Deweese had modelled at the age of 18 and was not employed by Dallas at the time, most parents motioned that the example she set wasn’t conducive to teaching students who were separated by only a few years in age. Consequently her employment was terminated.

11 Kim Kardashian

Curvy Kim Kardashian, encouraged by her mom to bare all for Hefner’s readers, stripped down for a 12-page spread in December 2007. By all accounts Kris Jenner was insistent: “Do it and you'll have these beautiful pictures to look at when you're my age.” Well, that sort of advice is all well and good if you’re going to refuse to embrace old age and spend your twilight years looking wistfully at pictures of you when you were in your twenties.

Anyway, Kardashian, reportedly one of the most beautiful women in society (whatever that means), did the shoot and was supposedly pressured by then step-dad Caitlyn Jenner to go the whole way with the naked thing. Looking back, Kardashian didn’t feel right about it although no one quite knows why. But in an interview since, she admitted: “I’m sorry I did Playboy, I was uncomfortable.”

10 Vanna White


Sometimes, no matter how hard you try to keep things on the downlow you still eventually get found out. That’s exactly what happened to American “Wheel of Fortune” hostess Vanna White.

Back in 1987, the then 30-year-old beauty of Stateside prime-time was running on empty and down on her luck. “Too embarrassed to ask [her dad] for rent money,” White took a punt on some lingerie shots to make a little extra money. The sense that she shouldn’t have done the shoot was strong with this one, and to make matters worse, a certain p--n mogul purchased the pictures and published them in Playboy despite White asking him not to.

So, all in all, the experience left her a little unhappy but she did have a word of warning to girls finding themselves in a similar position: “Never do anything you don’t want to do.”

9 Jessica Barth

Now for something a little different. American stage and film actress Jessica Barth, known for her roles in the Ted film franchise as Tami-Lynn McCafferty, has modelled for Playboy yet doesn’t immediately seem to regret it. However, keep in mind that she was able to model on her own terms which meant a bikini rather than 100% nude. OK, it’s not as demonstrative as an Edinburgh wool jumper and corduroy slacks but it is a step up from stark naked; as she explained to Loaded back in 2015, “I have nothing against people who do nudity and the images can be really beautiful, but that just wasn’t for me.”

And the reason she’s included in our run-down is because ever since then she has been passionately focussed on dispelling the airbrushed lies of modern-day photography and extolling the natural beauty of woman. “There is an army behind every photoshoot working on people. It’s art and that’s what it should be called. It’s not reality and young girls shouldn’t think that way.” Good for her!


8 Lara Stone


Another victim of someone taking advantage of outsourced photo syndication was Lara Stone. Ms Stone had done a photoshoot for fashion house Calvin Klein back in 2008. Little did she know her photographer Greg Lotus sold the pictures to French Playboy without authorisation. Naughty!

As it happened, Stone was not at all happy when she found herself plastered over the publication and sued the magazine and Greg Lotus. The Dutch supermodel was awarded “significant” damages in 2010 and was quoted as saying: “Playboy had no right to publish these unauthorized photographs. It’s not the kind of publication I would ever choose to appear in.”

7 Daisy Lowe

Although English fashion model Daisy Lowe chose to pose for Playboy as well as Esquire in 2011, she reportedly had regrets about the former. Not that there is anything she can do about it now, but her fully nude underwater pictures in a swimming pool in the September issue of that year had her wishing she had kept a little more dignity.

In an interview conducted by Grazia magazine (‘a weekly interactive digital magazine for intelligent women’), Lowe was asked what pictures of her she wished could be erased from the net. Her reply was colourful and curt: “Probably my completely nude Playboy picture. I love so many of the images, but not the one of me underwater. My lady parts got an entire page to themselves, which I would love to be deleted!”

6 Paige Young


OK, so up until now you’ve enjoyed some fairly light-hearted reading but let’s delve into the truly destructive side of life at the Mansion. Enter Paige Young who at 24 years old became Hugh’s Playmate of the Month in November 1968.

Young was given access to the lavish lifestyle Hefner promised any visitors to the Mansion, but did she really enjoy it? And did the arrival of a certain Bill Cosby into her life force her already shaky existence to take a nose dive? A close friend of Young said that the relationship between her and Cosby, “wasn’t healthy. Paige always seemed in a stupor, a daze. He looked like he was controlling her.”

Whether it was this or her initial decision to pose for the magazine that brought her to the end no one knows to this day. Nevertheless, Paige did end it all in 1974.

5 Jessica Alba

Another legal case. Hugh, when will you ever learn? When a woman says “no” she means it!

Playboy wanted Jessica Alba. In 2006, she was considered a starlet of Hollywood and, as we already know, the magazine loves starlets. So, the editors went head-hunting and finally tracked down some images of the American actress in a bikini.

Alba’s instruction was quite specific: yes, you can use some images of me from Into the Blue (a movie where “pecs and bikinis rule as Jessica Alba and the late Paul Walker search for undersea treasure”) wearing a bikini but don’t put them on the cover, OK?

The rest, as they say, is history; the magazine got sued for doing exactly the opposite, although she later dropped the lawsuit after receiving a personal apology from Hugh Hefner.

4 Carla Howe


Berkshire-born glamour model Carla Howe complained about the famous mansion being “stuck in the 1980s” after she visited it back in 2015. And that wasn’t the only thing that left her wanting. In an interview with The Sun back in the day, Howe groused that, “'Hef is so frail he goes everywhere with a group of nurses,” and “spends most of his time playing chess.”

Having visited off-and-on during the heyday of the enterprise, Howe and her sister saw how quickly a preconceived notion can fall flat on its face. She told the Mirror in the same year that, “at 7pm, Hef leaves the table for a screening of one his beloved old films, after which he goes straight to bed,” and that the night-time curfew of 9 p.m is like “being in a prison”.

3 Gloria Steinem

Using the alias of Marie Catherine Ochs, author Gloria Steinem sought to address the imbalance of the sexual revolution 1950s and 60s, which to that point had been largely male-dominated. At the height of Hefner’s powers, she infiltrated his empire to expose the truth behind the supposed glamour.

Keeping a secret diary of the sexual and financial advantages taken of often vulnerable young girls working as Bunnies, Steinem published "A Bunny's Tale" in the May and June issues of Show magazine in 1963. Making her report an intensely personal experience, she conveyed the seedy life Hef’s employees were expected to endure.

“A Bunny’s Tale” continues to stand as a searing indictment of the Playboy brand.

2 Chloe Goins


Back in January 2015, a serious allegation was made against Hugh Hefner in respect of regular visitor to the Playboy Mansion, Bill Cosby. Chloe Goins claims that when she was 18 years old, and again in 2008, Cosby, “helped her to a bedroom” but her next memory is of being naked with him licking her toes.

It isn’t the first time allegations have emerged about American comedian Cosby, but formal model Goins also alleged last year that Hugh Hefner “did nothing to stop the sexual assault” and that he allowed Cosby to use the Mansion as his own in order to violate her and others.

1 Izabella St. James

In her 2006 book “Bunny Tales: Behind Closed Doors at the Playboy Mansion” Isazbella St. James writes about the contrast of Hugh’s public and private image and the restrictions placed on those living at the Mansion. She tells of curfews and isolation, the limited sexual prowess of the Hef and more besides.

To say it was a dream come true would be a considerable overstatement and the reality of Holmby Hills is portrayed as far from appealing. Allowances would be sanctioned for underperformance in bed or some other minor indiscretions such as a disagreement between Bunnies or spending too long away from the Mansion. What’s more, St. James writes about how girlfriends fell in “pecking and bed order” and how a life that seemed to hold promise quickly turned “shabby and cheap”.


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