What Really Happened To These Famous Playboy Playmates?

Of all the bespoke titles that can be bestowed upon one in pop culture, few have historically projected as much glamour as "Playboy Playmate." Playboy magazine was founded in 1953 by former Esquire copywriter Hugh Hefner, who saw a market for material aimed at thoughtful, suave, sophisticated men (or men who fancied themselves as such), who also enjoyed seeing tasteful, artfully composed photographs of attractive women in the buff. 

Over the years, the brand — with its instantly recognizable bunny logo — would become iconic, known not only for Playboy magazine's stone-cold legit journalism and interviews, but for its "Playboy Club" nightclubs, for Hefner's notorious parties at the lavish "Playboy Mansion," and yes, for its centerfolds.

A goodly number of already-famous women have used Playboy appearances to stoke fires under their careers — Madonna, Drew Barrymore, and Jaime Pressly included. But many more used their status as "Playmate of the Month" — or as the recipient of the even more sought-after title of "Playmate of the Year" — as their launching pads into the world of entertainment. Here are a few of the most famous Playmates of all time, and what they're doing today.

Pamela Anderson

Pamela Anderson is perhaps the most famous celebrity ever to have been a Playmate. After beginning her career as a spokesmodel for Labatt's beer, the Canadian bombshell posed for Playboy magazine for the first time in October 1989, before being crowned Playmate of the Month just a few months later, in February 1990. Later in the decade, her career simply exploded; she appeared on the classic sitcom "Home Improvement" and on the syndicated action series "Baywatch," among other projects, appeared on the cover of Playboy a dozen more times, and became one of the most dominant sex symbols of the '90s.

After that decade, Anderson largely fell out of the limelight — thanks in large part to a certain home video made with her former husband, Motley Crue drummer Tommy Lee, and her devotion to their sons, Brandon and Dylan. She's also dedicated herself to the Pamela Anderson Foundation, established in 2014, which advocates for a diverse array of activist and non-profit organizations, including the International Fund for Animal Welfare, the National Sexual Violence Resource Center, and ... Wikileaks, among many more.

Recently, she's also gone public about departing from her glamorous past in dramatic fashion — by going completely makeup-free. "I just thought, 'I'm doing this for all the girls out there,'" she told Vogue in 2023. "I've had stepdaughters in past relationships and my sons have girlfriends, and this was for them. In this day and age, do we even know what a face looks like anymore? This is it."

Victoria Silvstedt

Hailing from Sweden, Victoria Silvstedt had already been a Miss World finalist and a model for all manner of high-end fashion brands when she was happened upon by Hugh Hefner in 1996. 

Her Playboy journey was a whirlwind one; Hef arranged a photo shoot in late October, Silvstedt appeared as the December Playmate of the Month, and she was named Playmate of the Year in short order, appearing on the cover of the June 1997 issue. She continued to be an in-demand model, and also made appearances in a handful of Hollywood features, including "BASEketball," "Boat Trip," and on TV series like "Melrose Place" and "Son of the Beach."

Silvsted has continued to serve as a spokesmodel for a slew of major brands, but that's not all — in an interview with Pallazzo magazine, she revealed that she has a background in finance, and has been an avid investor since 2009. "After the bank crash I lost some money, so I took my portfolio [into] my own hands," she explained. "I started trading equities and bonds ... I'm buying and selling some real estate also." 

Barbi Benton

Barbi Benton was never actually Playmate of the Month, but given her strong association with the brand, she may as well have been the '70s "Playmate of the Decade." She was still just a teenager when she appeared in several episodes of "Playboy After Dark," a variety series hosted by Hugh Hefner, which ran for just two seasons in 1969 and 1970. 

Her first Playboy cover came in July 1969, and over the next decade-plus — thanks in part to her years-long status as Hefner's girlfriend — she would appear on three more covers and in multiple pictorials. She also popped up early and often on the small screen throughout the '70s, notably on the variety series "Hee-Haw," and on such primetime hit series as "Charlie's Angels," "The Love Boat," and "Fantasy Island."

Benton's relationship with Hef ended in 1976, and in 1979, she married real estate tycoon George Gradow; she effectively retired from show business in the mid-'80s. They remain married to this day, and even though Gradow got into some serious hot water with the IRS in 2006 — even spending just over a year in federal prison — it's safe to say the pair have landed on their feet. They reside in a crazily futuristic-looking 24,000-square-foot mansion in Aspen, Colorado, which was featured on a 2011 episode of MTV's "Extreme Cribs."

Shannon Tweed

Canadian model and actress Shannon Tweed was a rising star on the pageant circuit in her home country when she landed a seemingly minor gig that would change the course of her life. She appeared on proto-reality series "Thrill of a Lifetime," in which average Canadians were given the chance to live out longtime dreams — which, in Tweed's case, was the opportunity to meet Hugh Hefner. 

Her wish was granted, and the meeting bore all of the fruit she possibly could have hoped for; she briefly dated Hefner, became Playmate of the Month for November 1981, and was named 1982's Playmate of the Year. Tweed parlayed her success into even more success; in addition to reigning over all direct-to-video "erotic thrillers" in the '80s and '90s, she carved out a respectable career in mainstream television, appearing in guest spots on shows as varied as "L.A. Law," "Murder, She Wrote," and "Frasier." 

But she may actually be best known as the longtime girlfriend of the prehensile-tongued KISS bassist Gene Simmons, whom she began dating in the early '80s. She starred along with Simmons and their two children, Sophie and Nick, on the A&E reality show "Gene Simmons Family Jewels," and in 2011, the pair finally went ahead and got hitched after nearly three decades together.

Shanna Moakler

Shanna Moakler lived in the public eye for years before she became Playmate of the Month in December 2001; she won the title of Miss USA in 1995, she was a regular on the TV series "Pacific Blue," and she was in a high-profile but rocky relationship with boxer Oscar De La Hoya, with whom she had her daughter Atiana. After the end of that relationship, she moved on to one that was even more high-profile — with Blink-182 drummer Travis Barker, whom she married in 2004.

Along with their two children, Landon and Alabama, the couple starred on the MTV reality series "Meet The Barkers" in 2005 and 2006 — but unfortunately, their union also ended in divorce in 2008. Moakler went on to appear on reality series such as "Celebrity Big Brother" and "Dancing With the Stars," but in recent years, she has gone back to her roots — as a producer of the Miss USA and Miss Teen USA Nevada pageants. 

Kelly Monaco

Kelly Monaco's road to stardom began in the pages of Playboy; After making Playmate of the Month in April 1997, she quickly picked up a few guest roles on series such as "Baywatch" and "Spin City," but found her home on daytime television, appearing in a main role on the soap opera "Port Charles" from 2000 until its cancellation in 2003. She wasn't out of a job for long — she immediately jumped ship to the iconic, long-running series "General Hospital," in which she has held down the role of Sam McCall for two decades and over 2000 episodes.

Interestingly, Monaco has a special place in the history of another long-running television staple: in 2005, she became the first-ever winner of "Dancing With the Stars," along with her partner, Alex Mazo. (Her win prompted a bit of an online backlash from fans who felt that the other finalists, Charlotte Jørgensen and John O'Hurley, turned in the better performance.) 

Monaco remains a key piece of the ensemble of "General Hospital" as of early 2024 — but she never forgot where she came from. Upon Hugh Hefner's death in 2017, Monaco took to Instagram to post a throwback photo of herself in bunny ears next to Hef; it was captioned, "My start, my soul, my family ... I will always remember and never forget. Hef, may you Rest In Peace."

Sara Jean Underwood

Oregonian Sara Jean Underwood had never given any thought to modeling before Playboy scouts spotted her while visiting Oregon State University for a "Girls of the PAC-10" pictorial. "I didn't think I was pretty enough," she would later tell the Associated Press. "I'm five-three, short, freckle-faced ... It wasn't a thought in my mind that I could do something like that." 

Not only did she make the cut for the pictorial, but she also landed on the cover of the October 2005 issue in which it appeared. She followed that up by landing in the centerfold as the Playmate of the Month in July 2006, and a year later, she was named the 2007 Playmate of the Year. Upon learning of the honor, she told the AP, "I thought I was going to puke. I thought I was going to faint. I thought I was going to cry."

Underwood parlayed her Playboy success into several film roles, including "Epic Movie" and "Miss March." In 2019, she and her boyfriend Jacob Witzling launched the YouTube channel "Cabinland," detailing their building of picturesque wooden cabins in the middle of the wilderness. In more recent years, she has starred in some videos with extremely adult titles, which we will not be sharing here.

Tiffany Fallon

As a young woman, Tiffany Fallon's future appeared to lie squarely within the world of sports. She earned her college degree in Sports Management from Florida State University, and her first high-profile gig was as a cheerleader for the Atlanta Falcons in the late '90s. Her stunning good looks, though, soon steered her in a new professional direction; she won the title of Miss Georgia USA in 2001, and placed second in the national competition. In November 2004, she was featured as the November Playmate of the Month, and in 2005, she secured the coveted Playmate of the Year title — becoming, at the age of 31, one of only three women to do so in their thirties.

Fallon parlayed the win into small roles in several feature films, but her public life since her Playmate days has been dominated by her very public relationship with, marriage to, and divorce from Joe Don Rooney, the lead guitarist for country outfit Rascal Flatts. The couple were linked since 2003, married in 2006, and had three children together before Baker filed for divorce in 2021. 

The contentious proceedings dragged on for some time, with the court ultimately finding that both parties had played a part in derailing the marriage by way of extramarital dalliances, although the breakup of Rooney's band and his alcohol misuse were also contributing factors; the divorce was finalized in 2023.

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Teri Weigel

Teri Weigel might have ruled all Playmates in the '80s; her visage first graced the cover of the magazine in November 1985, and she became Playmate of the Month six months later; she used her newfound fame as a springboard to appearances in movies such as "Predator 2" and TV shows like "Married With Children." 

But a 1990 car accident derailed her budding mainstream career, so Weigel chose to go in the opposite direction — a decision that made her nothing short of infamous in Playboy circles. In 1991, Weigel embarked on an adult movie career that stretched for 30 years and over 230 titles. She is one of only Playmates to ever do so, a distinction that earned her the extreme ire of Hugh Hefner, whom Weigel claims used his influence to hinder her adult career in whatever way he could, including getting her blacklisted from '90s porn giant Vivid Video. 

Nevertheless, at her peak, Weigel is estimated to have earned six figures as a porn actor — a career that was still earning her a paycheck as of 2021.

Ines Rau

French model Ines Rau first appeared in a Playboy spread in 2014, an appearance which promptly led to a contract with a modeling agency and a number of gigs for high-end brands. She returned to the mag's pages in November 2017 as its Playmate of the Month — an appearance that was nothing short of history-making: Rau is the first (and, thus far, only) transgender Playmate in the magazine's illustrious history.

In her conversation with the magazine for her spread, Rau had wise words to offer, saying, "It's a salvation to speak the truth about yourself, whether it's your gender, sexuality, whatever ... The people who reject you aren't worth it. It's not about being loved by others; it's about loving yourself" (via The Hollywood Reporter). She also expressed her desire to carve out a career in Hollywood, an aspiration she has begun to fulfill. She popped up in a small role in 2021's "The Souvenir: Part II," and in an episode of the hit Netflix series "Emily in Paris" the following year. She's also continued her career as a fashion model, and appeared in an episode of the Georgio Armani web series "Crossroads." 

Heather Rae Young

Heather Rae Young landed her first Playboy spread after attending an open call at the age of 20, and just a few months after its publication, she was named Playmate of the Month for February 2010. She subsequently appeared in a number of minor films, and became well-known for the four years she spent as a cast member on the high-end real estate reality series "Selling Sunset," beginning in 2019 — but in recent years, she's made headlines for making an unconventional move to a different realm of reality television.

This is by way of her marriage to Tarek El Moussa of "Flip Or Flop" fame, who divorced his former wife and co-star Christina Hall in 2018. El Moussa and Young met in 2019, tied the knot in 2021, and welcomed their first child together in 2023. It was probably only natural, then (especially with Young's background in real estate) that she should join her new husband in his televised house-flipping endeavors; the first season of their HGTV reality series, "The Flipping El Moussas," premiered in March 2023. 

Speaking with Us Weekly, Heather Rae (now) El Moussa expressed that she has a fine relationship with Hall, who shares two children with Tarek. "It's so nice to have a good relationship with the other parent because everyone's happier," she said. "Me and [Hall] communicate well, and we talk almost every single day about the kids and it's just important. We're raising good humans."

Crystal Hefner

Crystal Harris, the December 2009 Playmate of the Month, moved into the Playboy Mansion after Holly Madison moved out — not as Hef's new girlfriend, but as his wife, remaining married to him until his death in 2017. But life in the Playboy Mansion with Hugh Hefner wasn't exactly a fairytale. 

Hef's trio of former "girlfriends" — Madison, Bridget Marquardt, and Kendra Wilkinson — who served as the stars of the infamous reality series about that life, "The Girls Next Door," have all said some of the worst things former Playmates have said about the Playboy Mansion. Madison, who spent seven years in the mansion, even wrote a tell-all book, "Down the Rabbit Hole," detailing all of the weird rules that Hugh Hefner's girlfriends had to follow, after moving out — and Harris' experience was no different. 

In 2024, she dropped a book of her own: "Only Say Good Things," which basically confirms Madison's assessment of life in the mansion as a sort of cross between a sex cult and a living hell. "I did things that I wasn't comfortable with ... I was just trying to get through it. And the other girls? Nobody liked each other," she explained to The Guardian. "I went along with everything for so long, but I was brainwashed, really. How was that all OK? I was in the middle of it for a decade and I'm still trying to figure it out." To this day, she goes by the name Crystal Hefner, and she makes her living not in showbiz, but as a high-powered real estate agent in Los Angeles.