Category: Women of Playboy Stories By Laura Diez

Vanna White, national treasure best known as the longtime cohost of Wheel of Fortune, had to pay her bills pre-fame with some jobs she isn’t particularly proud of (like many aspiring stars!). In 1982, just before she landed her role on Wheel of Fortune, Vanna White modeled for lingerie catalogs. She beat out 200 other models, earning her spot on Wheel later that year. In 1987, however, at a career peak – those photos came back around. Her “friend” Hugh Hefner had purchased private photos of Vanna White and put her on the cover of Playboy Magazine against her wishes. [See More…]

Sandy and Mandy Bentley were two of the most iconic women of the late ’90s, early 2000s – brought into the public eye as twins dating Hugh Hefner at the same time, during his first group of multiple girlfriends. We’ll overview how Sandy and Mandy landed at the Playboy Mansion, and the unfortunate crimes that followed them afterwards – including a Ponzi scheme, hundreds of thousands of dollars worth of jewels, and the untimely murder of two men. Find me everywhere: linktr.ee/literallylaurad Time stamps: 00:00 Intro 00:41 Bentley Twins’ upbringing 01:32 Meeting Hugh Hefner 02:58 Twin “gimmick” and iconic style [See More…]

Our newest RHOC, Carmella Garcia, joins a decent group of Real Housewives that have a history with Playboy Magazine. We are overviewing Carmella’s time with the brand: from her appearance as a contestant on “Who Wants to be a Playboy Centerfold?” to becoming Playmate of the Year 2004. Plus, why we all loved her on Girls Next Door, and her time as a WWE Diva. We’ll then go through the eight Real Housewives that appeared in Playboy Magazine – plus two honorable mentions. Find me everywhere: linktr.ee/literallylaurad Time stamps: 00:00 Intro 00:44 Carmella + Who Wants to be a Playboy [See More…]

On the week marking what would be Marilyn Monroe’s 100th birthday, we are revisiting (and reframing) one of the most famous brand relationships she was understood to be a part of: Playboy Magazine, serving as their first ever cover model. We’ll overview the story of why Marilyn posed nude in the first place, how Hugh Hefner got his hands on the rights to those images, and her own reflection on how she was used to generate millions (with not even a thank-you note). Plus, the follow-up invitation to pose for the magazine, after she posed unclothed in a swimming pool [See More…]

Marilyn Grabowski spent over 40 years as Playboy’s West Coast Photography Editor. Known as “Mo,” she was the woman who decided what was “sexy” for generations of Americans, discovering Pamela Anderson, Dorothy Stratten, and Anna Nicole Smith along the way. She formed friendships with women who came through her studio, and may have been the recipient of allegations about what went on at the Playboy Mansion. This is the complicated legacy of “Mo.” Find me everywhere: linktr.ee/literallylaurad Time stamps: 00:00 Intro 01:40 Youth 02:24 Photo Editor, Talent Scout 05:02 Artistic lens 06:21 Nose surgery 08:13 Pamela Anderson 10:08 Dorothy Stratten [See More…]

Mary O’Connor was Hugh Hefner’s secretary for over 40 years, and unofficially served as a “house mother” to the women of the Playboy Mansion throughout her time. We’re discussing Mary’s early life and career at Playboy, her presentation on Girls Next Door, and her role as confidante and friend to the women. Plus, the controversy: the allegations of what her job truly entailed, and where her ultimate loyalties lied. Could Mary have been truly a friend to the women that were vulnerable to a system that she was responsible for maintaining? Find me everywhere: linktr.ee/literallylaurad Time stamps: 00:14 Early career [See More…]

Christie Hefner, Hugh Hefner’s daughter, served as President and CEO of Playboy Enterprises (and is the longest running female CEO of a publicly traded company!). We’re exploring her legacy and impact on how the brand continues to be remembered. She also made some interesting, diplomatic points through her few public statements, acknowledging the progressive workplace she was fostering internally, versus the negativity their product was associated with, culturally, and the life her father led. Find me everywhere: linktr.ee/literallylaurad Time stamps: 00:00 00:52 Kimberley Conrad video update from Crystal Hefner 02:01 Family, Early Career 04:17 Business Decisions 06:26 Christie’s Playboy vs [See More…]

By popular demand, we’re visiting the story of Carrie Leigh: the 19-year-old model who became Hefner’s live-in girlfriend for five years… and then sued him for $35 million. Carrie Leigh was the first person on record to refer to the world of Playboy as a “cult.” We’re covering her rise in the public eye as “first lady of the Playboy Mansion,” and the palimony suit alleging she was promised marriage, children, a Malibu beach house, and an annual salary. Plus: the (suspected?) allegation against Carrie Leigh by Jennifer Saginor, author of Playground, that they had a romantic relationship while the [See More…]

We’re exploring the story of Kimberley Conrad – Playmate of the Year 1989, Hugh Hefner’s second wife, and maybe one of the most overlooked women in the entire Playboy story. We’re getting into all of it: her January 1988 centerfold, being named the 30th Playmate of the Year in 1989, the wedding that surprised the nation, and raising two kids inside the “family environment” of the Playboy Mansion. Plus, the 1998 separation and the prenup, the house literally next door, the stories of her surveillance, and one of the very few times she broke her silence — to defend Hugh [See More…]

Sondra Theodore was only 19 when she began dating Hugh Hefner (age 50) – and over five years, beginning in 1975, she experienced increasingly traumatic situations at the Playboy Mansion. She shares her stories on two episodes of A&E’s Secrets of Playboy docuseries: on season one, she details manipulation and coercion, referring to herself as a “mule” for Hugh Hefner; and on season two, she and her daughter recount family-oriented events at the Mansion that turned into her daughter seeking refuge there at the same age Sondra was when she moved in. You can find the podcast, Characters, here on [See More…]