Throughout its 71-year history, Playboy has attracted hundreds of famous women—from models to actresses—eager to showcase themselves on its iconic pages. With Playboy’s founder, Hugh Hefner, passing at age 91, we reflect on some of the magazine’s celebrity covers.
Drew Barrymore
Barrymore posed for the cover of Playboy Magazine in January 1995, describing it as a personal adventure. She enjoyed the experience and emphasized her comfort with her body, seeing the human form as inherently beautiful.
Lindsay Lohan
Lindsay Lohan’s appearance in Playboy significantly boosted the magazine’s ad sales. The January/February 2012 issue saw a 55% increase in ad pages compared to the previous year, totalling just over 49 pages. TMZ.com reported that Playboy had offered Lohan $750,000 to pose while the actress sought $1 million. Eventually, Playboy negotiated a deal close to her asking price, according to TMZ. Lohan, who was 25 then, gained fame from Disney movies like “The Parent Trap.” However, her adult career struggled, marked by legal issues stemming from a 2007 conviction for drunk driving and drug use.
Kim Kardashian
In 2007, then 27-year-old Kardashian posed for Playboy adorned only with pearls. The photoshoot, featured on an episode of Keeping Up With the Kardashians, the family’s long-standing E! reality series, showcased a more explicit Playboy style without any shapewear to conceal traditionally obscured parts.
Marilyn Monroe
When the publication relocated to New York, Hugh Hefner was a promotional copywriter at Esquire magazine in Chicago. Opting to remain in Chicago, Hefner wanted to launch his own magazine. In December 1953, the inaugural issue of Playboy hit newsstands with a cover price of 50 cents, featuring Marilyn Monroe on the cover. Although Monroe did not pose specifically for Playboy, Hefner acquired the famous bare-body photograph taken by Tom Kelley from the John Baumgarth Calendar Company. Initially referred to as “Sweetheart of the Month,” the feature soon evolved into “Playmate of the Month.”
Sharon Stone
Sharon Stone rose to fame in the ’90s with “Basic Instinct,” following earlier films since 1980. Her role in “Total Recall” marked her breakout. Despite controversy over a revealing scene, Stone’s career thrived with roles in “Sphere” and “Casino.” Stone strategically posed for Playboy in 1990 to boost her film’s profile.
Kim Basinger
Kim Basinger appeared in Playboy’s February 1983 issue, marking a notable moment in her career. She gained prominence for her role as Domino Petachi in the 1983 film “Never Say Never Again.” Basinger went on to establish herself as a versatile actress, starring in diverse roles such as the lead in the acclaimed erotic drama “9½ Weeks,” Vicki Vale in “Batman,” and Lynn Bracken in “L.A. Confidential,” for which she received an Academy Award for Best Supporting Actress.
Pamela Anderson
Pamela Anderson started her journey with Playboy by appearing on its cover in October 1989. In January 2011, she achieved a milestone by becoming the most featured cover model in the magazine’s history with her 13th cover appearance. She is the last cover model.
Charlize Theron
Charlize Theron’s acting career took off in the mid-1990s, gaining prominence with roles in “The Devil’s Advocate” and other notable films by the end of the decade. Her portrayal of serial killer Aileen Wuornos in “Monster” earned her an Academy Award for Best Actress in 2003. Theron also ventured into modelling and endorsing products for brands like Dior. Despite posing for various magazines, she did not pose for Playboy. However, Playboy published unauthorized photos of Theron in its May 1999 issue, exploiting her rising star power.
Dolly Parton
Dolly Parton expressed ease with posing for Playboy’s cover in 1978, under the condition that she would be fully dressed. Parton, the first country music star to grace the magazine’s cover, styled herself in a Playboy bunny outfit featuring a black bustier, bunny ears, and a distinctive white bow tie attached to a pink collar.
Kate Moss
For its 60th anniversary, Kate Moss adorned the cover of Playboy in the iconic bunny outfit. The legendary supermodel also showcased an unprecedented 18-page pictorial inside, marking a significant milestone in the magazine’s history.
Carmen Electra
Carmen Electra, rose to fame in the 1990s as a Playboy model, but never considered herself a charmer. She recalls feeling “very shy” during her initial Playboy shoot in 1996. Despite her nerves, she persevered, and it proved worthwhile. She reportedly earned $500,000 for that appearance and gradually grew comfortable, appreciating the supportive environment. Subsequently, she posed for Playboy four more times.
Sherilyn Fenn
Sherilyn Fenn’s acting career began in the mid-1980s with roles in lesser-known films. Her breakthrough came as Audrey Horne in David Lynch’s acclaimed series “Twin Peaks,” which diversified her opportunities while avoiding typecasting. By the early 1990s, she graced magazine covers, including Playboy’s December 1990 issue, coinciding with her “Twin Peaks” fame. Fenn had previously appeared without clothes in the film “Two Moon Junction,” reflecting on this experience in her Playboy interview.
Farrah Fawcett
Farrah Fawcett rose to prominence as a symbol of love in the 1970s, fueled by an iconic poster in a red bathing suit and roles in “The Six Million Dollar Man” and “Charlie’s Angels,” which catapulted her to international fame. Initially hesitant about going without clothes, Fawcett first appeared on Playboy’s cover in December 1978, featuring partially clothed photos from earlier years. Over time, her views evolved, leading her to pose fully bare at 48 for the December 1995 issue and again at 50 for the July 1997 cover. Fawcett explained her evolving perspective: “A woman is more provocative, sensual, and mysterious with nothing showing.”
Jenny McCarthy
The well-known actress and advocate against vaccines initially appeared in Playboy in 1993, receiving $140,000 and the Playmate of the Month title. She subsequently won Playmate of the Year in 1994 and posed seven more times, with six covers.
Mariah Carrey
Although Mariah Carey appeared on the cover of the 2006 issue without posing without clothes. The singer used the opportunity to promote her tour for “The Emancipation of Mimi.”
Georgia May Jagger
Georgia May Jagger, at the age of 27, posed for Playboy in 2011, which attracted attention due to her famous parents, Jerry Hall and Mick Jagger. Her parents initially hesitated but eventually agreed to let her do the shoot. Georgia May Jagger has since built a successful career as a catwalk model and has been involved in various fashion shows, including walking for Tommy Hilfiger at London Fashion Week (LFW).
Madonna
In 1985, Madonna, known for her bold and unapologetic persona, curated her own vision for her Playboy cover. The images featured on the cover and inside spread were from an earlier phase in her career.
Cindy Crawford
In 1988, Cindy Crawford followed her instincts despite advice to the contrary. In Apple TV+’s documentary “The Super Models,” Crawford explained that she disregarded warnings against posing bare for Playboy during the late ’80s due to the magazine’s reputation. Crawford acknowledged the significance of Playboy’s platform and its symbolism but recognized that it was unconventional for supermodels to pose for the magazine at the time. Despite the reservations of others, Crawford ultimately trusted her own judgment and decided to pose for Playboy in 1988.
Denise Richards
After giving birth to her daughter Sam Sheen, Denise Richards posed for Playboy in 2004. She later explained the shoot to Sam and Lola after they discovered it themselves. Richards acknowledged that kids today can easily access information online, but she strives to be open and honest with her daughters about her past.
Anna Nicole Smith
Anna Nicole Smith graced the cover of Playboy multiple times throughout her career. Her appearances on Playboy covers, starting from March 1992 and subsequent issues, marked significant moments in her modelling and public persona, reflecting her iconic status in the world of entertainment and glamour.
Kelly Bensimon
In 2010, Kelly Bensimon posed for Playboy photographed by her ex-husband, renowned photographer Gilles Bensimon, expressing her excitement about appearing on the cover and showcasing her view at 41 years old to Page Six.
Elle MacPherson
Camille Grammer Meyer, known from RHOBH, posed for Playboy in her early modelling career and made a return to the magazine in 2011 following her involvement with the Bravo franchise.
Lisa Rinna
Lisa Rinna appeared in Playboy twice: first in 1998 while pregnant with her daughter Delilah Belle Hamlin, and again in 2009 for a cover and spread inspired by “The Graduate.”
Raquel Welch
In December 1979, Raquel Welch impressed fans with a striking photo on the cover of Playboy in a form-fitting red swimsuit. Welch achieved fame for her timeless beauty and her roles in strong female characters, which reshaped traditional perceptions of temptress. She posed for Playboy without, sued MGM Studio, and succeeded as a businesswoman.
Amanda Cerny
A pivotal moment in Amanda Cerny’s showbiz career was her feature as the ‘Playboy Playmate Of The Month’ in October 2011. Following this, her social media influence surged, leading to significant collaborations with major brands like Nike and Marc Jacobs, as well as fun videos alongside actors, musicians, and acting studios. Her videos continued to garner massive viewership; today, her Instagram page boasts an impressive 22 million followers.
Heidi Montag
Heidi Montag’s 2009 Playboy shoot, caused a stir due to its scandalous nature. The spread featured beach bikini photos and included intimate details about her married life with husband Spencer Pratt. Montag reportedly earned $1 million for the shoot.
Olivia Munn
In 2009, Olivia Munn had the opportunity to pose for Playboy but encountered unexpected challenges. Initially approached for a clothless shoot, Munn declined and detailed the experience in her 2010 memoir. She revealed that negotiations led to a “no pink” contract, allowing partially dressed without revealing certain areas.
Kylie Jenner
Kylie Jenner’s featured in Playboy’s “The Pleasure Issue,” directed by her partner Travis Scott and captured by her longtime photographer, Sasha Samsonova in 2019. She appeared in red lace lingerie with a diamond Playboy bunny necklace, though her face was notably not visible. The decision behind this, whether Kylie or Travis initiated it, raised questions and stirred varied reactions, yet her appearance was striking, leaving observers intrigued and supportive as long as she was comfortable with the portrayal.
Azaelia Banks
Rapper Azealia Banks posed for Playboy, appearing in the April 2015 issue. She described her feature as a provocative pictorial aimed at ‘breaking the internet.’ Ellen Von Unwerth photographed her. In addition to the sultry images, the outspoken rapper also gave a candid interview.
Daryl Hannah
Daryl Hannah, known for her roles in films like “Blade Runner” and “Splash,” appeared on the November 2003 cover of Playboy, although she was reportedly unhappy about it. Despite her prior agreement to approve all published photos, Hannah expressed frustration off-air with Howard Stern a month before the issue’s release, hinting at potential legal action that did not materialize publicly.
Bo Derek
Bo Derek, renowned as one of the quintessential symbols of of love in the 1980s, graced the covers of Playboy four times: in 1980, 1981, 1984, and 1994. Her appearance solidified her status as an icon of beauty and appeal during that era.
Kristy Swanson
Kristy Swanson, best known as the original Buffy Summers, adorned Playboy’s November 2002 cover, reflecting on her career and cultural impact. Kristy Swanson began her acting career in the early 1980s, appearing in several notable films. Swanson continued acting in various movies, along with gaining popularity with her Playboy cover.
Vanna White
Vanna White reflected on her lengthy career in entertainment, expressing regret over a lingerie photoshoot that propelled her onto Playboy’s cover in 1987. The controversial images nearly cost her the role of Wheel of Fortune’s letter-turner, a position she has held for over three decades. Despite legal efforts to mitigate the fallout, including lawsuits against Playboy and Hugh Hefner, White acknowledged it as a mistake made out of financial necessity early in her Hollywood career.
Barbra Streisand
Streisand appeared on Playboy’s 1977 cover in a bunny shirt, posing with the caption: “What’s a nice Jewish girl doing on the cover of Playboy?” Later, she regretted not allowing a full bunny costume shot. In a 1996 interview, Streisand reflected on her decision, questioning why she felt compelled to apologize for embracing her intelligence, filmmaking, and physical attributes.
Joan Collins
Throughout her career, Joan Collins has exuded charisma, but what surprised many about her Playboy cover was her age—she was 50 at the time. The veteran Hollywood actress, now 82 and still flourishing, challenged stereotypes about ageing, stunning in a red plunging gown on the cover.
Anna Faris
Anna Faris, famous for her comedic talents in Scary Movie, gained attention on the 2008 Playboy cover during the promotion of House Bunny. Portraying a Playboy Bunny in the film, Faris surprised many with her appearance on the magazine cover despite her comedic reputation.
La Toya Jackson
Despite initially presenting her topless Playboy shoot in 1989 as a statement of independence against her conservative upbringing, LaToya Jackson has since disclosed that it was coerced by her abusive ex-husband. She regrets her involvement and asserts she would never repeat the experience.
Donald Trump
The provocative Playboy magazine cover featuring Donald Trump from around 1990 adorned the billionaire’s New York office for years. Positioned alongside accolades from religious organizations and articles from other magazines that lacked explicit content, the cover and accompanying interview in the March 1990 issue were seen as prestigious achievements for Trump, aligning him with prominent figures in politics and entertainment featured by the publication.
Bruno Mars
Bruno Mars was the 10th man to be featured on the cover of Playboy, appearing in the magazine’s April issue, released on March 16, 2012. He shares the cover with Raquel Pomplun and is also showcased in a fashion spread and interview, as well as modelling designs from Marc Jacobs, Louis Vuitton, Dolce & Gabbana, and others.
Bettie Page
In January 1955, Bettie Page often hailed as the “Queen of Pinups,” was immensely popular among young men of the fifties and admired by Hugh Hefner, who held her in high regard both professionally and personally. This special magazine issue typically sells for over $450 online, with some sources valuing it at over $800.
Dita Von Teese
Model and burlesque performer Dita Von Teese graced the cover of Playboy’s December 2002 issue. Originally named Heather Renée Sweet, Von Teese adopted her full stage name, which was an error during her Playboy shoot. In an interview with Vogue, she explained that she had used the name “Dita” for years, inspired by the actor Dita Parlo. When Playboy asked for a last name, she chose “Von Treese” after finding it in a phone book. However, due to a mistake, they published her name as “Von Teese,” ultimately becoming her iconic stage name.
Kelly Monaco
After being featured as Playmate of the Month in the April 1997 issue of Playboy, she ventured into acting, securing roles in multiple soap operas and a recurring part on “Baywatch.” Her Playboy debut opened doors to a diverse career in television, showcasing her talent beyond modelling.
Goldie Hawn
For the January 1985 issue of Playboy, Goldie Hawn posed provocatively inside a giant martini glass on the cover, showing her playful and vivacious persona. The image captured attention for its blend of glamour and humour, characteristic of Hawn’s appealing personality.
Chelsea Handler
In December 2009, a Playboy cover featured a playful Chelsea Handler in a gold string bikini and matching boots, playfully tugging at her bottoms while posed as a supersized candy cane. When the cover was unveiled, Handler, known for her humour about drinking and marijuana use, quipped that she had “quit drinking for about a day and a half” to prepare her body for the photo shoot.
Shannon Tweed
Shannon Tweed appeared on the cover of Playboy magazine. She was featured as the Playmate of the Month in the November 1981 issue and later appeared on the cover of the magazine in November 1982. Shannon Tweed is a model and actress known for her work in both Playboy and mainstream films and television shows. She was romantically involved with Playboy founder Hugh Hefner around the same time, residing in the mansion for fourteen months.
Jayne Mansfield
Jayne Mansfield appeared on the cover of Playboy magazine’s February 1955 issue. She was an American nightclub performer, singer, and actress. Despite her brief acting tenure, she received a Golden Globe award for her role in The Wayward Bus (1957). Tragically, she passed away in a car accident in Biloxi, Mississippi, in 1967.
Barbi Benton
Barbi Benton, originally Barbara Lynn Klein, was among the leading Playboy Playmates. At 18, she appeared on Playboy’s entertainment program, Playboy After Dark. Benton was romantically involved with Hugh Hefner from 1969 to 1976 and was featured in the magazine on six occasions. After retiring, she settled down with her husband, George Gradow, and she advocates for Hefner’s legacy of empowering women.
Sara Jean Underwood
Sara Jean Underwood is recognized as an actress, adult model, and television host, notably for her role as a host on Attack of the Show! She began her modelling career with a feature in Playboy in October 2005. Underwood also appeared in several episodes of The Girl Next Door on E!.
Jamie Pressly
Jaime Pressly, recognized for her comedic performances in “My Name Is Earl” and “Not Another Teen Movie,” graced the cover of Playboy magazine in February 2004. Her appearance underscored her boldness and marked a notable moment in her career as both an actress and a model.
Shannen Doherty
Shannen Doherty posed for Playboy after her departure from “Beverly Hills, 90210,” and again in 2003 after leaving “Charmed.” She was featured on the cover of the December 1993 issue of Playboy.
Tara Reid
Tara Reid, known for roles in iconic films like “The Big Lebowski” and “American Pie,” posed for Playboy in February 2010. Her Playboy appearance occurred later in her career, marking a departure from her earlier successes in Hollywood comedies to a new phase of public exposure and image.
Joan Baez
Folk singer and activist Joan Baez posed for one of the most artistic covers in Playboy’s history by being photographed upside down in water in 1970.
Agnes Laurent
French actress and model Agnes Laurent, who often posed, made an appearance on the cover of Playboy in 1958. She posed with the iconic Playboy bunny print strategically covering her.
Jessica Hahn
Jessica Hahn, primarily known for her involvement in a scandal with televangelist Jim Bakker, posed for Playboy and appeared on the cover in November 1987. Her appearance garnered significant attention at the time, marking a controversial moment in the magazine’s history.
Debbie Harry
Debbie Harry, the lead singer of Blondie and a music icon known for her distinctive voice and style, graced the cover of Playboy magazine in March 1980. Her appearance underscored her status as a boundary-pushing artist and cultural figure during the height of Blondie’s success in the late 1970s and early 1980s.
Naomi Campell
In 1999, Naomi Campbell made her debut on the American cover of Playboy, marking the start of her appearances on a total of 18 Playboy covers across 16 countries. This was also the year she signed her first global cosmetics contract with Cosmopolitan Cosmetics, as reported by Vogue. Captured by David LaChapelle in London, Naomi, then 29 and among the highest-paid models globally, shared with the magazine, “I work very hard and I’m worth every penny.” She also disclosed her approach to maintaining her renowned physique, stating, “I never diet, I smoke, I drink occasionally, and I don’t exercise.”
Seth Rogan
Seth Rogen appeared on a cover alongside model and TV host Hope Dworaczyk in the April 2009 issue, engaging in a playful shoot reminiscent of Marilyn Monroe. In the interview accompanying the photos, Rogen expressed his aspiration to set a trend for Jewish men who share his appearance.
From iconic actresses like Marilyn Monroe and Sharon Stone to music legends such as Madonna and Debbie Harry, each cover story has shaped public perceptions of beauty, style, and empowerment. Despite controversies and changing societal norms, these covers have often been transformative moments in the careers of these individuals, showcasing their charisma and defining beauty beyond their primary professions.
If you think we have forgotten a name, then let us know in the comments section.
