Hugh Hefner was always the biggest star in the room no matter who else was there. And he had the largest entourage of any star I had ever seen.
I know because I worked for the mogul for three years, bringing celebrities such as Pink, Jaime Pressly and Paris Hilton to his famed Playboy mansion in Holmby Hills, California when I served as the West Coast Bureau Chief for Playboy magazine from 2003 until 2006. Everyone was star struck.
The Illinois native – who never woke up before 12 noon, ate scrambled eggs for breakfast every day and had a deep passion for old Hollywood movies – was one of the most charming people I ever worked for, calling me ‘darling’ and asking if I was ‘doing fine.’ But he also could be one of the most demanding bosses around.
For years the icon, who died Wednesday in LA, wanted Britney Spears on the cover and became obsessed with the idea.
The man in his silk pajamas: Hugh Hefner was a charming man, but a tough boss. I worked as his West Coast Bureau Chief of Playboy magazine from 2003 until 2006
His gal: The editor was obsessed with getting Britney Spears on the cover of the magazine and her manager said she was considering it, but she never got close. Here she is seen in February
Parker flanked by Playboy models Devin Devasquez, left, and Fiona Horne, right, in 2004 at the Playboy mansion
Working for Hef was one of the best and worst experiences of my life.
The Playboy mansion was gorgeous even if it was dated with worn-out place mats and Lays chips for appetizers. And his friends and family were warm and kind, especially his brother Keith.
But there was always that feeling that you had to deliver big for Hefner or you would get fired.
Hef was dead set on having Spears on the cover in 2004. Actually, he always wanted her on the cover, from the day she turned 18-years-old. He had a crush on her.
He even faxed me a typed memo about it. The memo basically read, ‘I want Britney Spears for the cover. Signed, Hef.’
One night I brought Jennifer Tilly to the mansion. I think she just wanted to meet the man and sadly she was not that friendly once she got there. She didn’t seem impressed by anything. And Hef didn’t even know who she was.
He pulled me aside in the foyer of the Playboy mansion. Hef looked handsome in his silk pajamas with his silver fox hair brushed to the side.
He met her: Pink was brought up to the Playboy mansion in 2004, but she never agreed to do the cover. Seen here in 2010
‘I want Britney for the cover. I don’t want anyone else. I want Britney or no one! Get her to do it. It would sell like crazy,’ he barked.
I told him it would take time, but looked good. In truth, her manager Larry Rudolph said it was a possibility but I never believed it.
I offered someone else. ‘Pink is interested,’ I said.
He wasn’t barking anymore. His cold look turned warm and he smiled. ‘Sounds good darling,’ he said as he touched my arm. ‘But don’t forget Britney!’ He winked at me and walked off.
Hef was deaf in one ear so conversations were not easy, and he kept them short.
For a year I had talked to Pink’s team to try to get her on the cover of Playboy. She was open but wasn’t sure.
She did it though: In August 2004 Eva Herzigova took the cover and Hef loved that he had landed another supermodel after Cindy Crawford and Elle Macpherson did the magazine
So I asked her to dine with me and Hef as well as 20 of his closest friends at his private dining room table at the mansion.
She arrived late and was hung over as well as sunburned from a party she had been to that day. I gave her water and food and told her to relax. During the movie in his screening room she slept in an oversized chair.
I was excited to introduce her to Hef after the film ended, to show him I was doing my job well and was close to getting her to pose for the magazine. The deal had not been ironed out, but she was considering going topless.
Bullying his way: Donald Trump was on the cover in 1990 with Brandi Brandt and demanded to be on the cover again in 2004 but Hefner said, ‘Ewwww’
When I brought her up to Hef, he greeted her warmly like he does with every woman.
He shook her hand and took a photo and called her ‘darling.’ Every woman is darling because he can’t remember anyone’s name.
He greeted me warmly too, like an old friend. ‘How are you? So good to see you again darling,’ he said. I have to admit I liked how polite and kind he could be.
Hours later during an after party in the back garden by the famed grotto, I threw back vodka tonics with Pink and she told me how she had been discovered. She was the most normal celebrity I had ever met.
Hef and his ladies: At the time Holly, Bridget and Kendra were living at the mansion. Here they are seen in 2004
It seemed like a successful night.
So you can imagine my surprise when I was told the next day that Hef didn’t even know who Pink was. He didn’t even recall meeting her at the dinner. I was baffled. He seemed excited about having her on the cover. A colleague who had worked for Playboy for decades simply told me: ‘That’s Hef!’
She loved Playboy: Jaime Pressly at the mansion in 2003
He wanted Britney Spears on the cover. That was the goal. Why couldn’t I land Britney?
The next time I went to the Playboy mansion to have dinner with Hef I brought a TV actress who was not that well known. He was nice to her too.
He asked me about Britney again. He was obsessed it seemed.
‘Soon, after her next album,’ I said. I kind of made that up. The truth is, she could have done it. It was impossible to tell.
‘Eva Herzigova wants to do the cover,’ I offered in hopes of keeping my job.
‘Who?’ he barked like I had just said something crazy.
I gained courage. ‘She is one of the best models in the business and has a massive following, I think she could do as well as Cindy Crawford or Elle Macpherson did.’ Both those supermodels had sold well for the magazine.
She did the cover as well: In February 2004 Jaime posed for the cover and attended the Playboy Super Bowl party in Houston
‘Sounds good darling, sounds good,’ as he walked away into the company of his girls Bridget, Holly and Kendra.
Hef – no one was ever allowed to call him Hugh or Mr Hefner – never let his star pals see how tough he could be.
Like that time Donald Trump called Hef at home in 2004 and demanded he be on the cover with the female cast of The Apprentice.
Three of the women from the first season of The Apprentice wanted to pose nude for the magazine. But Trump stepped in and said they could only do so if he was on the cover with them.
Hef said ‘Ewww.’
They were real friends: Paris Hilton with Hef in 2004; she let him put her image on the cover though she did not pose nude
Her cover: Hilton was happy to give this image to her longtime pal Hefner in 2005 but she did not pose inside; here is her tribute shared on Thursday
Trump had been on the cover before in 1990 with model Brandi Brandt. And Donald’s assistant told me it sold so well that we should be begging for him to do it again.
Hef said no, and he let me take the fall on that one, telling Trump that Heidi Parker didn’t like the idea. Like I had any say. I never did.
Donald was not happy with this news. The icon let Hef know I should be fired, I learned through Hef’s secretary. ‘Donald thinks he’s friends with Hef but they’re not friends and there is no way Hef wants Trump on the cover again!’ Hef’s secretary told me.
I was shocked Trump wanted me fired and even more shocked Hef pretended to be his friend but really didn’t like him at all.
Another hit: Daryl Hannah took a 2003 cover. Hef said he wanted her to ‘look like Daryl from the movie Splash’
From Beverly Hills, 90210 to Playboy: Shannen Doherty took the December 2003 cover
Hefner loved his celebrities: Denise Richards posed for the 2004 cover of Playboy when she was still married to Charlie Sheen
I went to Hef’s mansion several times after that, making sure people like Willa Ford and her boyfriend at the time UFC Light Heavyweight Champion Chuck Liddell came (they had a run in with her frenemy Paris which almost led to a fist fight with Liddell and Paris’ bodyguard).
Other stars that I worked with were Jaime Pressly and Leonardo DiCaprio, who loved the Halloween bash because he could wear his wolf mask and stare at people without being recognized. He found humor in this.
I also worked hard to land a deal to get Ashanti to sing at the 50th anniversary party in New York City in 2003. Hef didn’t care. He didn’t know who she was. But he was thrilled Pamela Anderson showed up at the last minute.
She came unpaid and asked for nothing, not even a hotel room. Pam was kind and gracious and truly loved Hefner. And he thought she was the biggest star in the world.
I left the magazine in 2006 after getting Denise Richards, Brooke Burke, Joanna Krupa, Shannen Doherty, Daryl Hannah, Jaime Pressly, Debbie Gibson, Carmen Electra and Jenny McCarthy (they were vets but getting them to do the cover again was not easy), Rachel Hunter, Charisma Carpenter, Peta Wilson, Teri Polo, Bai Ling, and Jessica Canseco to pose for the cover.
But no Britney Spears. Sorry Hef.
His lady: I also worked hard to land a deal to get Ashanti to sing at the 50th anniversary party in New York City. He didn’t care. He didn’t know who she was. But he was thrilled Pamela Anderson showed up at the last minute. Seen in December 2003