I was half way through my first year of law school when I received a call that changed the course of my life. It was my friend Bill, who was calling to ask me if I would be interested in an internship in Playboy’s legal department. I initially laughed it off, but I soon realised he wasn’t joking. This was the beginning of my 15 year relationship with the bunny.
After interning at the Playboy offices throughout summer, I was offered another position that fitted into my law school schedule. As the holidays approached, so did the company holiday party, but I wasn’t technically an employee. When I heard it was to be at the Playboy mansion, I couldn’t believe I didn’t get an invitation. This could have been my only chance - every major celebrity for the last few decades had hung out and partied at the famed mansion. Not only that, there might even be a chance to see Hugh Hefner, and the grotto! In a twist of fate, a colleague felt so sorry for me that she invited me to the party as her date.
On the night, I remember approaching the mansion in a shuttle bus (guests use the parking space nearby UCLA and are driven to the property by bus). After a brief exchange between security and our driver, the gates opened. And there it was. Just as it looked in the pictures and the movies.
There was a giant tent over the backyard, a dance floor, a DJ, and a huge buffet. As I walked around the grounds, I found the zoo, complete with a massive cage of spider monkeys, where you could walk in and hand feed the monkeys as they climbed all over you. I found the game house which housed Playboy and Hef themed pinball machines, a pool table and various pieces of original memorabilia. The game house also contained the “rubber room” - acircular room with a lush carpet floor covering several inches of rubber so one could bounce on it. The walls and ceiling were all covered in mirrors and the room was empty of any furniture, other than several pillows. I felt like a kid in candy store.
As I walked back to the party, I saw a small crowd gathering by the back door of the house. They were all clamouring to talk to Hef, who was coming out with five or six of his girlfriends to join the party. My friend Sal grabbed my arm and dragged me over to meet him. Once things calmed down, I walked up to him and introduced myself. He chatted with me for a few minutes and he seemed to genuinely be interested in who I was. It was surreal. Knowing that Sal had brought a camera, I said “Mr. Hefner, would you mind if I took a picture with you” and without missing a beat, he turned to me and said - “young man, I would be honored to take a picture with you.”
I could not believe it. Here was a man that had been friends with Frank Sinatra, Sammy Davis and every other major celebrity from the 1950s until now, and he was saying he would be honoured to take a picture with me - a lowly intern. I was so impressed with his response that it has stayed with me until this day. I remember thinking that he was the definition of a gentleman.
Over the next few years, I didn’t have any interaction with Hef - I was just a junior member of the legal department. As the years went on, and I became a vice president and senior vice president of the department, my interactions with Hef increased. For the most part, they consisted of phone calls from the mansion regarding various legal issues. Hef was always on his speakerphone and reminded me of Charlie from Charlie’s Angels. Face-to-face meetings were rare but whenever there was something to celebrate, we would be invited to the mansion. These events comprised the majority of my in-person interactions with him. Without exception, he was always polite, courteous and friendly.
My 15 years at Playboy were some of the best years of my life. Mr Hefner created an atmosphere that was inclusive and fun. When the company had something to celebrate, everyone would celebrate. It always felt like working for a family business that cared about its employees.
While people instantly associate Hef with the nude images that appeared in the magazine, most are not aware of what a trailblazer he was with respect to LGBT rights, civil rights, and freedom of speech. He was documented supporting gay rights as far back as 1955. The first Playboy Interview in 1962 comprised of Alex Haley (who went on to write Roots) interviewing Miles Davis. His show, Playboy’s Penthouse (1960), was one of the first TV shows to have both black and white performers on the same stage. He was a visionary who was far ahead of his time.
I truly feel honoured to have known him and am incredibly fortunate to have played a tiny part in the Playboy story.
Thursday, June 04, 2026
