15 Ladies Who Went After Hef And His Empire

It can’t be easy standing up to Hugh Hefner and the empire he's built.

The magazine has, for more than six decades, been a hugely successful corporation, with a lot more power and influence than most would care to admit. When the history of the 20th century is written, you can bet Hugh Hefner and his girlie magazine gets at least a passing mention for its culture influence – albeit controversial and a lot of it negative.

That's why it's so surprising when anyone attempts to take on a huge operation like Playboy. Not to mention financially ruinous if you take them to court. And considering how often Playboy has had to defend its nudie content over the years, you just know they have an army of lawyers on standby to handle whatever comes up.

Despite that, a surprising number of women have taken on Hugh Hefner and the Playboy empire in lawsuits and the court of public opinion. The women who have stood up to Hef are quite a diverse group - playmates, actresses, accountants, lovers, spouses, even royalty -

Of course, many of these incidents amount to little more than frivolous nuisance cases that have been settled out of court. But, in other instances, women have won cases that have changed the law. And there have also been books written about Playboy that have challenged the myth of  Hefner himself.

Here are just a few women who dared to challenge the Playboy empire:

15 Vanna White - Tried To Sue For $2.5M

The famed letter-turner of the long-running game show Wheel of Fortune paid a price when she burst onto the scene in the early 1980s. Becoming famous overnight meant that her past was suddenly under scrutiny. In 1987,  Vanna White had to sue Playboy for $5.2 million to stop them from publishing lingerie photos – one showing a semi-nude glimpse of her derriere – that were shot way back in 1982.

The magazine purchased the photos from a photographer for $100,000 and planned to place one on the cover (the derriere shot). “I made a mistake. I’m sorry and I just hope I don’t lose my job over it,” Vanna said at the time.

She didn’t, and the lawsuit disappeared. The Playboy issue was published, and the photos proved rather tame. It didn’t seem to damage her squeaky-clean image one bit. White, now 60, continues to turn the letters on Wheel of Fortune.

14 Lara Stone - Won Her Suit And Got An Apology

Model Stone took the fight against Playboy across the water to France. In 2010, Playboy France – a much more fashion-oriented version of the mag – bought nude photos of Stone from photographer Greg Lotus and promptly published them.

Stone had previously appeared nude in magazines like W and Purple. But those magazines got her a-okay before doing so. Playboy France published the sexy photos without her permission. She first heard about it through the press. So Stone sued and won “significant” damages and a published apology in the next issue.

“No woman wants photos of them to be published in Playboy without permission,” Stone said later. “I'm very pleased to have won the case, although of course, I would rather not have had to take legal action at all.”

Stone donated the unspecified lawsuit money to the Great Ormond Street Hospital.

13 Liz Dickson - Sued For $500K Due To A Painful Golfing Incident

A silly one, but also a bit creepy.

In 2012, the model and Playmate was paid to appear at a Playboy golf event. Sometime during the golf excursion, Dickson agreed to lie face down on the ground and grip a tee with her butt cheeks. One guesses this is common at a Playboy event. With Dickson face down on the ground, a local radio host then placed a ball on the tee and swung a driver.

He missed, and Dickson sustained what can only be described as a huge and real ugly bruise. She insisted that she only thought she was posing for a picture (which hardly makes it more understandable). But a YouTube video of the moment appears to indicate she knew exactly what was happening.

Nonetheless, Dickson sued Playboy for $500,000 for pain and suffering. Amazingly, Playboy would settle the suit with Dickson in 2015 for an undisclosed amount.

12 Paige Young - Took Her Life And Said Hef Was The Devil 

A strange story. This one was all about revenge from beyond the grave, though it didn’t quite work out that way. Only now are we learning of the details of the life and suicide of Paige Young, Miss November 1968. She was a popular gal who became a popular visitor to the Playboy Mansion and dated many powerful Hollywood men, including Bill Crosby.

Turning 30 in 1974, Paige is said to have grown depressed. She felt used by the men who once fought for her attention. So, after allegedly announcing her intentions, Paige shot herself. According to friend Melanie Meyers, Paige lay in a pool of blood on top of an American flag draped over her bed. The room was covered with photos and clippings of Hugh Hefner, along with the alleged scrawled words “Hugh Hefner is the devil”. A suicide note is said to have spelled out her anger at the men in her life. One can't help feel a tell-all book might have done the trick less tragically.

As revenge plots went, it didn’t work. Young’s suicide generated little attention and it’s only in recent years the details have begun to emerge.

11 Catherine The Great - Nude Painting Defamed The Monarch, Lawsuit For 100M Rubles 

To be fair, the Russian monarch had been dead for 200 plus years when a lawsuit was filed on her behalf against the Russian edition of Playboy. So, it wasn't like she had a problem with appearing in the girlie mag.

The Academy of Sciences and the St. Petersburg Centre for Gender Issues both filed a suit against the magazine in 1996 after it ran a drawing of Catherine lounging nude with several other famous Russian women. The suit claimed the portrait did “Harm to the women’s dignity and professional reputation of the women”.

Not too sure how you can defame a dead person's professional reputation but that didn’t stop them from asking for 100 million rubles. The painting’s artist Dmitry Vrubel couldn’t understand what all the fuss was about, commenting that “Catherine The Great was ugly. I made her beautiful”.

I’m pretty sure Vrubel offended a lot more women with that comment than any nude picture of a dead monarch ever did.

10 Terri Welles - Fought The Mag To Use Some Of Their Popular Words

The 1980 Playmate of the Year ran a website in the 1990s where she sold pictures of herself to all her adoring fans. The site mentioned she had appeared in Playboy and even used the magazine’s familiar rabbit logo.

Playboy didn’t like that so much. They sued Welles in 1998 for copyright infringement, claiming they owned the exclusive commercial rights to the words “Playboy” and “Playmate of the Year”.

But Welles didn’t back down. She fought the magazine. And won. Well, mostly won. The case of Playboy Enterprises Inc. v. Welles wrapped up with the court deciding that Welles had not infringed on Playboy by using those particular words. However, the court did rule that Welles couldn’t use the rabbit logo anymore.

Welles eventually took down the site in 2006, saying it had been “a fun ride”.

9 Izabelle St. James - Bad-Mouthed Hef And The Mansion In Her Book

St. James, a law student, met Hefner at a Hollywood nightclub back in 2002. She quickly became one of his many live-in girlfriends, proudly paraded around in public for the cameras. St. James eventually turned her mansion memories into a best-selling 2009 tell-all book, Bunny Tales: Behind Closed Doors At the Playboy Mansion. It tells a sordid tale of group sex, A-Lister actor romps (Charlie Sheen figures prominently), Viagra and filth (but not the sexy kind). Turns out, the Playboy mansion is something like a dump, with stained mattresses and dog poop on the rugs.

St. James wrote that the shabby rooms featured mismatched furniture. "It was as if someone had gone to a charity shop and bought the basics for each room," she wrote. Interesting how shabby furniture and a stained mattress seem the most shocking things in a book about Hugh Hefner.

8 Holly Madison - Bad-Mouthed Hef In Her Book

A showgirl and model, Holly Madison became one of Hugh Hefner’s live-in girlfriends in the early part of the new millennium. The antics in the mansion were played out on TV in the E! series The Girls Next Door. It painted a happy, only slightly naughty picture of life at the mansion. By the end of her relationship with Hefner, Madison had become his #1 girl. She talked about marriage and children. Hefner was having none of it.

After their mostly amicable split, Madison put pen to paper, writing the best-selling Down The Rabbit Hole. It portrayed Madison’s experiences at the mansion as miserable, with Hef a constant controlling presence. Sex with Hef was a depressing ritualistic group affair. The book was a best-seller, leading to a second book, The Vegas Diaries, and the reality series Holly’s World.

For his part, Hefner denied everything. “Over the course of my life I’ve had more than my fair share of romantic relationships with wonderful women," the Playboy founder said. “Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can’t win 'em all!"

7 Chloe Goins - Hef Connected To Cosby Assault Case

Even at 90, Hugh Hefner continues to be involved in legal problems. In this current case, he’s been tagged as a “co-conspirator” with a Bill Cosby sexual assault case that allegedly occurred on his watch. The model and dancer – who has previously dropped a civil suit against Cosby – says that she was approached by Hefner and Cosby at the Playboy Mansion in 2008 when she was 18. After Cosby gave her drink, she became ill. Hefner advised her to lie down. When she woke, Cosby was allegedly sucking her toes with his pants down.

This isn’t the first time Hefner’s name has come up in connection to Cosby assaulting women. In another case, a woman alleged that she was assaulted by Cosby at the Playboy Mansion back in 1974. A longtime friend of Cosby, Hefner initially came to the comedian's defense.  “I would never tolerate this kind of behavior, regardless of who was involved,” Hefner said at the time.

The case is still before the courts.

6 Jessica Alba - Sued For Cash, Got An Apology Instead

Here’s another Playboy instance of using photos without telling the person actually in the photos. Actress Jessica Alba appeared in a bikini on the March 2006 Playboy cover beside the headline “25 Sexiest Celebrities”. Trouble was, Alba had refused to do any such thing. The magazine just used a photo from the publicity stills for her then-current movie Into The Blue. Alba felt that by appearing on the cover, Playboy was implying she appeared nude inside.

Well, duh. Of course, they were. Readers must have felt really ripped off once they got the magazine home and discovered no nude Jessica inside.

So she sued, asking the magazine to stop distributing the issue and pay her a “monetary settlement”. Eventually, Alba just settled for an apology from Hugh Hefner himself. He also made donations to two of Alba’s favorite charities.

5 Corri Fetman - Sued For Harassment

A Chicago lawyer who first got famous for her billboard slogan “Life’s short. Get a divorce.” Fetman eventually appeared in an eight-page pictorial in Playboy. Soon after, she began writing a legal column called “Lawyer of Love” for Playboy’s online mag.

But things went sour in 2008 when Fetman left (or was fired) by Playboy. She sued the magazine for sexual harassment she said she received from a Playboy executive in charge of online publications. According to Fetman, exec Thomas Hagopian sent her sexually explicit emails and phone messages, firing her when she rejected his advances.

Playboy responded by suing Fetman right back, claiming she had infringed on Playboy’s copyright by continuing to use the column name “Lawyer of Love”.

The result of either case isn’t clear (A non-disclosure agreement, maybe?) though Fetman still has a blog she calls “Love Lawyer”.

4 Catherine Zulfer - Sued For Age Discrimination And Wrongful Dismissal

An accounting executive with Playboy for 30 years, Catherine Zulfer knew how things worked at the magazine. So when her bosses asked her to approve a million dollars in bonus for upper management, she balked at the idea. She pointed out that bonuses need to be approved by Playboy’s board of directors first. And she raised her concerns with both Playboy’s Chief Financial Office and Chief Compliance Officer.

This didn’t sit well with her bosses. They fired her. And she sued them right back – for both age discrimination and wrongful dismissal. The whistleblower case eventually led to a record-breaking settlement ($6 million for Zulfer) that subsequently led to other large payouts for corporate whistleblowers. A Playboy case that affected the law? It happened.

3 Joey Heatherton - Sued For $2M And Settled Out Of Court

She was the Go-Go girl of the 1960s, known for her sexy dancing and versatility. Heatherton was a triple threat – working as an actress in TV and movies, as well as singing (She had several hits) and dancing. Bob Hope loved her, taking her on his USO tours for over a decade.

Nudity wasn’t a problem for Heatherton. She did lots of nude or semi-nude photo shoots over the years. But when Playboy published a semi-nude still of her from a movie (Bluebeard), she sued. The $2 million suit claimed invasion of privacy and unlawful use.

The case was quietly settled in the subsequent years. Heatherton’s career since then has been a series of legal problems and multiple comebacks. One such comeback occurred in 1997 when, at 53, Heatherton became a Playboy cover girl, and posed nude for an eight-page spread. Apparently, she had worked out her differences with the magazine.

2 Kim Conrad (Hefner) - A Nasty Divorce

Hugh Hefner’s second wife was a Playmate of the Year who he married in 1989. Though they separated in 1998, Kim Conrad continued to live in the mansion next door with their two children.

Hefner explained this arrangement years later. "At the time of the separation, I was happy to get a divorce,” he said. “I only remained married for the sake of the children at her request."

But that all ended in 2009 when the couple filed divorce papers. Kim is said to have sought $5 million and $40,000 in monthly child support.

Things got nasty pretty quick at that point, with Hefner selling the second house right out from under Kim, leading to a lawsuit.

Hefner also took the opportunity to claim his wife cheated on him and not the other way around. The case was settled in 2010.

1 Cybill Shepherd - Sued The Company And Settled

The Moonlighting star burst onto the Hollywood scene with the classic 1971 Peter Bogdanovich film The Last Picture Show. In that black-and-white period drama about a small Texas town, Cybill Shepherd appeared nude briefly in several scenes alongside co-star Jeff Bridges.

But a few years later, Shepherd was forced to sue Playboy. The magazine had run an “unauthorized” topless still from a deleted scene from the movie without telling her (or anyone associated with the film for that matter).

Shepherd settled with the magazine a year later. As for the deleted scene, it would appear in a re-release of The Last Picture Show several decades later with Cybill’s apparent blessing. She is said to have liked how her breasts looked and personally asked Bogdanovich to insert the scene in the movie.

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