FOR decades, Playboy has been a springboard for many women seeking fame, fortune, and influence.
While some have used their spotlight to become best-selling authors, others have managed to build a business empire.
Playboy of the front cover of their January 2005 edition featuring Jenny McCarthy[/caption]
Hugh Hefner kissing Pamela Anderson at a party in 2003[/caption]
Hugh Hefner with Holly Madison and Bridget Marquardt kissing him on the cheeks in 2007[/caption]
From self-made billionaire Diane Hendricks to entertainment powerhouse Jenny McCarthy and cultural icon Pamela Anderson, these women have transformed their early experiences with Playboy into lasting success – earning millions.
Here, YASMIN HARISHA takes a look at how they turned their moments in the magazine into multimillion-dollar fortunes.
Diane Hendricks
£17.8 billion
Before becoming a billionaire businesswoman, Diane Hendricks worked as a Playboy Bunny.
In the late 1960s, she took on the role to support herself and her child after becoming a mother at just 17 years old.
While Diane did work as a Playboy Bunny during her younger years to make ends meet, her role was primarily within the Playboy Clubs rather than being directly involved with Hugh Hefner himself.
Her time as a Bunny served as a stepping stone before she transitioned into real estate.
Later, she co-founded ABC Supply – a wholesale distributor of building products such as roofing, siding, windows, and doors.
Today, Diane, 77, is recognised as one of America’s wealthiest self-made women.
Jenny McCarthy
£16.6 million
Jenny McCarthy first rose to fame as a Playboy model in the early nineties, earning the title of Playboy’s Playmate of the Month in October 1993.
A year later, at the age of 21, she was named Playmate of the Year, a milestone that catapulted her into the spotlight.
From there, she began building her wealth, with the exposure from Playboy opening doors to television hosting opportunities, including her own programme, The Jenny McCarthy Show.
Now 52, Jenny also ventured into acting, appearing in popular films and shows such as Scary Movie 3, BASEketball, and Two and a Half Men.
The former Playboy Bunny has further expanded her earnings by authoring several bestselling books and, in 2019, joining The Masked Singer as a panellist.
Holly Madison
£12.65 million
Holly Madison playboy cover[/caption]
Bridget Marquardt, Sara Jean Underwood, Hugh Hefner, Christi Shake, Shauna Sand, Holly Madison and Kendra Wilkinson attend the 2007 Playmate of the Year[/caption]
She rose to fame as one of Hugh Hefner’s girlfriends and a prominent figure in the Playboy Mansion, having moved in during the early 2000s at the age of 21.
Holly, now 45, became widely recognised through the reality TV show The Girls Next Door, which focused on Hugh’s girlfriends, including Kendra Wilkinson and Bridget Marquardt.
She also boosted her earnings by starring in the Las Vegas burlesque production Peepshow for three and a half years, ending her run on October 21, 2012, which became a significant source of income.
In addition, Holly has authored bestselling memoirs, including Down the Rabbit Hole and The Vegas Diaries, where she detailed her experiences in the Playboy Mansion and her life beyond it.
Now a mother of two, the model has amassed 1.2 million Instagram followers, enabling her to earn through sponsored posts and brand collaborations, including partnerships with FashionNova.
Kendra Wilkinson
£4.75 million
February 2009 Playboy magazine cover featuring Kendra Wilkinson[/caption]
Joining Holly on the rich list is another of Hugh Hefner’s ex-girlfriends, Kendra Wilkinson, who made a name for herself as one of the main figures in the Playboy Mansion after moving in back in 2004 at just 18 years old.
She quickly became a fan favourite on the reality show The Girls Next Door, which ran from 2005 to 2010.
During that time, she was also named Playmate of the Year in 2008.
Now 39, Kendra used her fame to launch her own reality shows, including Kendra (2009–2011) and Kendra on Top (2012–2017), which gave viewers a glimpse into her married life with former NFL player Hank Baskett.
The pair, who are now divorced, share two kids – 14-year-old Hank Baskett Jr. and 10-year-old Alijah Baskett.
Crystal Hefner
£3.9 million
Crystal Hefner and Hugh Hefner at a Halloween party in 2015[/caption]
Crystal Hefner first rose to fame as a Playboy Playmate, earning the title of Playmate of the Month in December 2009, which launched her career in the spotlight.
Her profile grew even more after she married Hugh Hefner in December 2012, becoming his third wife at the age of 26, while Hugh was 86 – marking an age gap of 60 years.
Although much of her early fame was tied to her relationship with Hugh, Crystal continued to make a name for herself after The Girls Next Door.
Now 38, Crystal has focused on healing and starting a new chapter in her life.
In January 2024, she released her memoir, Only Say Good Things: Surviving Playboy and Finding Myself, which offers a candid look at her childhood and her time at the Playboy Mansion.
Pamela Anderson
£15.8 million
Playboy magazine cover featuring Pamela Anderson in 2017[/caption]
The Canadian-American actress first gained fame as a Playboy Playmate, making her debut as Playmate of the Month in February 1989 at the age of 22.
Her popularity soared, and she was named Playmate of the Year in 1990.
Over the years, Pamela graced the cover of Playboy 14 times, cementing her status as one of the brand’s most iconic figures.
While Playboy launched her career, her success extended far beyond modelling.
Facts you didn’t know about the Playboy Mansion
Girlfriends vs Playmates
Rumour has it that Hugh Hefner would have two to a dozen “girlfriends” living with him at a time. These girlfriends are not to be confused with Playmates. Each girlfriend had their own room, but one “special lady” was named as girlfriend number one and stayed with Hef in his room. Each girlfriend received a $1,000 (£760) weekly bonus “allowance.”
Hef’s Wild side
The Playboy mansion was home to a private zoo. It was one of very few private residences that actually has a zoo license. Hefner was a fan of birds. Among his collection – many of which roamed the grounds – were peacocks, macaws, flamingos, toucans and ducks.
The Elvis Legend
Within the mansion was a secret room, called “The Elvis Room.” Legend has it that the King himself, Elvis Presley, had a little slumber party in the room with up to eight eager bunnies.
She achieved global fame portraying C.J. Parker on Baywatch (1992–1997), one of the most-watched television shows of the decade.
Her image as a sex symbol, combined with her Playboy exposure, opened the door to acting roles, brand endorsements, and public appearances.
Now 57, Pamela has ventured into various fields, including launching her own fragrances, participating in television specials, and becoming a vocal animal rights advocate, working closely with PETA.
Her high-profile relationships, such as her marriage to Tommy Lee, along with later pursuits like writing, have also kept her firmly in the public eye.
Hugh Hefner and Holly Madison outside The Standard Hotel in 2003[/caption]
Hugh Hefner and Crystal Harris at their wedding with their dog in 2012[/caption]
Diane Hendricks, CEO of ABC Supply Co., smiling at a company meeting in 2015[/caption]
