Marilyn Monroe was featured in the very first issue of Playboy in 1953 — making her the most iconic Playmate in the magazine's history. From Monroe to Pamela Anderson, who holds the record with 151 covers across 31 countries, Playboy has showcased some of the world's most famous women since its debut.

Source: UGC
TABLE OF CONTENTS
Key takeaways
- A Playmate is a female model featured in the centrefold/gatefold of Playboy magazine's Playmate of the Month (PMOTM).
- At the end of the year, one of the 12 Playmates of the Month is named Playmate of the Year (PMOTY).
- Every PMOTM is awarded $25,000, while each PMOTY receives an additional $100,000, plus a car (on a short-term lease) and other discretionary gifts.
- Marilyn Monroe is considered a precursor to the Playboy Playmate title.
- Donna Michelle is the youngest Playmate of the Year at 18. She received the title in 1964.
- Pamela Anderson holds the record for the most Playboy covers, with 151 appearances across 31 countries.
Methodology
This list ranks the 45 most famous women who appeared in Playboy magazine, ordered by cultural impact, career longevity, and their significance to the magazine's history. Rankings draw on cover appearances, Playmate of the Year titles, and wider public recognition across entertainment and modelling.
Summary table: top 15 Playboy Playmates
Rank | Name | Key stats |
1 | Marilyn Monroe | First Playmate, 1953 inaugural issue |
2 | Pamela Anderson | Most covers — 151 in 31 countries |
3 | Anna Nicole Smith | 1993 Playmate of the Year |
4 | Carmen Electra | Five Playboy features |
5 | Jenny McCarthy | 1994 Playmate of the Year |
6 | Shannon Tweed | 1982 Playmate of the Year |
7 | Cindy Crawford | Two pictorials (1988 and 1998) |
8 | Dita Von Teese | December 2002 cover |
9 | Jayne Mansfield | February 1955 Playmate of the Month |
10 | Barbi Benton | Six appearances (1969–1976) |
11 | Victoria Silvstedt | 1997 Playmate of the Year |
12 | Tiffany Fallon | 2005 Playmate of the Year |
13 | Teri Weigel | Two appearances (1985–1986) |
14 | Sara Jean Underwood | 2007 Playmate of the Year |
15 | Hope Dworaczyk Smith | 2010 Playmate of the Year |
Playboy magazine has featured numerous iconic models and played a significant role in launching and furthering their careers. Most celebrities who posed for Playboy continued being household names in their own right even after they stopped working for the magazine.
1. Marilyn Monroe (first Playmate, 1953 inaugural issue)

Source: UGC
- Nationality: American
When Playboy was first published in December 1953, the inaugural issue featured unclothed photographs of Marilyn Monroe. Her image on the first issue's centrefold established the template for every Playmate that followed.
Monroe, born June 1, 1926, became one of the most iconic figures in American popular culture. She died on August 4, 1962, aged 36. Marilyn Monroe's Playboy appearance is now considered a landmark moment in the magazine's history.
2. Pamela Anderson (most Playboy covers — 151 in 31 countries)

Source: UGC
- Nationality: Canadian
Pamela Anderson holds the record for the most Playboy covers by any individual, with 151 appearances across 31 countries, including 12 in the US between 1989 and 2007. She was born on July 1, 1967, and first appeared as a Playboy Playmate in February 1990.
She was also the last person to pose unclothed for the magazine. Pamela Anderson appeared on the 2015 cover, closing a more than 60-year tradition of uncovered photography.
3. Anna Nicole Smith (1993 Playmate of the Year)

Source: UGC
- Nationality: American
Anna Nicole Smith became Playboy's May 1992 Playmate of the Month before being named 1993 Playmate of the Year. She was born on November 28, 1967, and died on February 8, 2007, aged 39.
Her career extended beyond modelling to television and film, including the reality series The Anna Nicole Show. Anna Nicole Smith's rise from waitress to Playboy cover model became a defining story of 1990s pop culture.
4. Carmen Electra (five Playboy features)

Source: UGC
- Nationality: American
Carmen Electra, born Tara Leigh Patrick on April 20, 1972, has appeared in Playboy five times, beginning in 1996. Her regular features cemented her status as one of the magazine's most prominent returning models.
Best known for her role in Baywatch and her subsequent pop-culture presence, Electra became one of the most recognisable faces associated with Playboy in the 1990s and 2000s.
5. Jenny McCarthy (1994 Playmate of the Year)

Source: UGC
- Nationality: American
Jenny McCarthy, born November 1, 1972, appeared as Playboy's October 1993 Playmate of the Month and was named 1994 Playmate of the Year. She parlayed her Playboy fame into a media career spanning television, writing, and activism.
6. Shannon Tweed (1982 Playmate of the Year)

Source: UGC
- Nationality: Canadian
Shannon Tweed, born March 10, 1957, was named Playboy's 1982 Playmate of the Year. She lived at the Playboy Mansion for 14 months during her association with the magazine.
Tweed went on to an acting career in film and television, and is also known as the long-term partner of rock musician Gene Simmons of the KISS rock band.
7. Cindy Crawford (two pictorials — 1988 and 1998)

Source: UGC
- Nationality: American
Cindy Crawford, born February 20, 1966, appeared in Playboy pictorials in 1988 and again in 1998. Her two appearances with the magazine span a decade of her career as one of the world's most successful supermodels.
Crawford also participated in the docuseries The Supermodels, alongside fellow icons Naomi Campbell, Linda Evangelista, and Christy Turlington.
8. Dita Von Teese (December 2002 cover)

Source: UGC
- Nationality: American
Dita Von Teese, born Heather Renée Sweet on September 28, 1972, appeared in Playboy three times before securing the December 2002 cover. Her artistic burlesque aesthetic set her Playboy appearances apart from the magazine's typical style.
Von Teese has become one of the world's most celebrated burlesque performers, maintaining a distinctive retro-glamour brand throughout her career.
9. Jayne Mansfield (February 1955 Playmate of the Month)

Source: UGC
- Nationality: American
Jayne Mansfield, born April 19, 1933, was Playboy's February 1955 Playmate of the Month. She was among the earliest Hollywood actresses to appear in the magazine, at a time when such appearances were highly unusual for established stars.
Mansfield died on June 29, 1967, aged 34, in a car accident. She remains one of the most memorable figures from Playboy's early era.
10. Barbi Benton (six appearances, 1969–1976)

Source: UGC
- Nationality: American
Barbi Benton, born Barbara Lynn Klein on January 28, 1950, appeared in Playboy six times over several years. She first came to public attention after appearing on Playboy After Dark at age 18 and maintained a close relationship with Hugh Hefner from 1969 to 1976.
Benton also pursued a country music career alongside her modelling work, releasing several albums in the 1970s.
11. Victoria Silvstedt (1997 Playmate of the Year)

Source: UGC
- Nationality: Swedish
Victoria Silvstedt, born September 19, 1974, was Playboy's December 1996 Playmate of the Month and was subsequently named 1997 Playmate of the Year. Before her Playboy appearances, she won the title of Miss World Sweden in 1993.
Silvstedt went on to an international modelling and acting career, becoming one of the few non-American women to win the Playmate of the Year title.
12. Tiffany Fallon (2005 Playmate of the Year)

Source: UGC
- Nationality: American
Tiffany Fallon, born May 1, 1974, was Playboy's December 2004 Playmate of the Month and was named 2005 Playmate of the Year. She previously won the title of Miss Georgia 2001.
Her Playboy appearances came at a time when the magazine was actively seeking models with pageant backgrounds, and Fallon's combination of competition success and centrefold work made her one of the decade's notable Playmates.
13. Teri Weigel (two appearances — 1985 and 1986)

Source: Getty Images
- Nationality: American
Teri Weigel, born February 24, 1962, appeared in Playboy twice: first on the November 1985 cover and then as the April 1986 Playmate of the Month. She also appeared in several Playboy video productions during this period.
Weigel subsequently transitioned to a career in adult films, making her one of the more unusual career trajectories among Playboy's alumni.
14. Sara Jean Underwood (2007 Playmate of the Year)

Source: Getty Images
- Nationality: American
Sara Jean Underwood, born March 26, 1984, began her association with Playboy in October 2005, was named July 2006 Playmate of the Month, and won the 2007 Playmate of the Year title.
She went on to host Attack of the Show! on G4 and built a significant social media following in subsequent years. Underwood has remained one of the more recognisable Playmates from the 2000s.
15. Hope Dworaczyk Smith (2010 Playmate of the Year)

Source: UGC
- Nationality: American
Hope Dworaczyk Smith, born November 21, 1984, was Playboy's April 2009 Playmate of the Month and was named 2010 Playmate of the Year. Her centrefold was photographed by Playboy veteran Stephen Wayda.
Dworaczyk Smith later married Black billionaire businessman Robert F. Smith, transitioning from modelling to philanthropy and entrepreneurship.
16. Brande Roderick (2001 Playmate of the Year)

Source: UGC
- Nationality: American
Brande Roderick, born June 13, 1974, was Playboy's April 2000 Playmate of the Month and was named 2001 Playmate of the Year. She is also known for her appearances in the Baywatch TV series.
Roderick later appeared on The Celebrity Apprentice and has remained active in entertainment and philanthropy.
17. Madonna (1978 art photographs, published July 1985)

Source: UGC
- Nationality: American
Madonna, born August 16, 1958, appeared in Playboy's July 1985 issue, but the photographs were archival images taken in 1978 during her early career as an art model in New York City. She received approximately $25 per session for the original shoots.
The images later sold at auction for up to $100,000. Madonna was already a global star by the time the photographs were published, which amplified their cultural impact enormously.
18. Drew Barrymore (1995 cover)

Source: UGC
- Nationality: American
Drew Barrymore, born February 22, 1975, appeared on Playboy's 1995 cover. She later expressed complicated feelings about the decision. Director Steven Spielberg, who had directed Drew Barrymore as a child in E.T., reportedly sent her a quilt covering the Playboy centrefold image as a gesture of concern.
Barrymore has since built one of Hollywood's most enduring careers, including her talk show The Drew Barrymore Show.
19. Lindsay Lohan (January–February 2012 issue)

Source: UGC
- Nationality: American
Lindsay Lohan, born July 2, 1986, appeared in Playboy's January–February 2012 double issue. The shoot deliberately echoed Marilyn Monroe's famous 1953 Playboy photos, with Lindsay Lohan adopting similar poses and styling.
The photoshoot attracted significant media attention and was one of the magazine's highest-profile celebrity issues of the early 2010s.
20. Chelsea Handler (December 2009 cover)

Source: UGC
- Nationality: American
Chelsea Handler, born February 25, 1975, appeared on Playboy's December 2009 cover — one of two covers she secured with the magazine. Handler is primarily known as a stand-up comedian, author, and television presenter.
Her Playboy appearances were unconventional for a comedian of her profile and were widely discussed in media at the time.
21. Brooke Shields (1986 cover, aged 21)

Source: UGC
- Nationality: American
Brooke Shields, born May 31, 1965, appeared on Playboy's cover in 1986 at the age of 21. She had been a child model since the age of 11 months and became one of the most photographed young women in the world throughout the 1970s and 1980s.
Her Playboy appearance at 21 came after years of controversy surrounding earlier naked photographs taken of her as a child — images that Brooke Shields later fought to suppress legally.
22. Geri Halliwell (1998 republication)

Source: UGC
- Nationality: English
Geri Halliwell, born August 6, 1972, appeared in Playboy in 1998 — though the photographs were originally taken for a British tabloid Page 3 shoot when she was 19. The images were republished by Playboy after she became globally famous as Ginger Spice of the Spice Girls.
Halliwell's association with Playboy was not a deliberate career move but a consequence of her pre-fame modelling work being acquired and republished.
23. Kate Moss (December 2013, 60th anniversary issue)

Source: UGC
- Nationality: English
Kate Moss, born January 16, 1974, appeared in Playboy's December 2013 issue, which marked the magazine's 60th anniversary. The 18-page spread featured Moss in a bunny outfit and a series of artistic photographs that blended her high-fashion image with the magazine's iconic aesthetic.
The issue was one of Playboy's most commercially successful of the decade and remains a landmark in Moss's long career.
24. Shannen Doherty (three appearances — 1993, 1994, and 2003)

Source: UGC
- Nationality: American
Shannen Doherty, born April 12, 1971, appeared in Playboy three times: December 1993, March 1994, and a ten-page pictorial in December 2003. She is best known for her roles in Beverly Hills, 90210 and Charmed.
Doherty died on July 13, 2024, aged 53, following a battle with breast cancer. She had been open about her diagnosis and treatment in the years before her death.
25. Sharon Stone (two appearances — 1990 and 1992)

Source: UGC
- Nationality: American
Sharon Stone, born March 10, 1958, appeared on Playboy's cover twice — in July 1990 and in the Christmas 1992 issue. Her Playboy appearances preceded her career-defining role in Basic Instinct (1992), which made her one of Hollywood's biggest stars.
She has since been recognised as one of the most significant actresses of her generation. Sharon Stone has earned Academy Award and Golden Globe nominations throughout her career.
26. Mariah Carey (March 2007)

Source: UGC
- Nationality: American
Mariah Carey, born March 27, 1969, appeared in Playboy's March 2007 issue. Her pictorial was notable for showing considerable skin while stopping short of going fully unclothed — a carefully managed approach that allowed her to appear in the magazine on her own terms.
She is one of the best-selling music artists of all time. Mariah Carey has consistently controlled her public image with exceptional care.
27. Charlize Theron (1999 cover — without consent)

Source: UGC
- Nationality: South African
Charlize Theron, born August 7, 1975, appeared on Playboy's 1999 cover through photographs taken during an earlier modelling engagement, without her consent. She unsuccessfully sued for the unauthorised publication of the images.
Theron went on to win the Academy Award for Best Actress for Monster (2003) and has established herself as one of Hollywood's most acclaimed performers. The Playboy case brought attention to the issue of models' rights over their images.
28. Denise Richards (December 2004, five months postpartum)

Source: UGC
- Nationality: American
Denise Richards, born February 17, 1971, appeared in Playboy's December 2004 issue just five months after giving birth. The decision to pose so soon after childbirth generated considerable media coverage.
She is also known for her roles in Starship Troopers (1997) and The World Is Not Enough (1999). Denise Richards' Playboy appearance came at a transitional point in her career.
29. Anna Faris (2008, promotional for The House Bunny)

Source: UGC
- Nationality: American
Anna Faris, born November 29, 1976, appeared in Playboy in 2008 in conjunction with the release of her film The House Bunny, in which she played a Playboy Bunny. The appearance blurred the line between promotional and genuine participation.
Faris is best known for the Scary Movie franchise and her television work, including the sitcom Mom.
30. Olivia Munn (two appearances — 2007 and 2009)

Source: UGC
- Nationality: American
Olivia Munn, born July 3, 1980, appeared on Playboy's February 2007 cover and in the July/August 2009 issue. She was working as a television presenter when she appeared, including on G4's Attack of the Show! and as an actress in Battlestar Galactica.
Munn subsequently moved into major film and television roles, including X-Men: Apocalypse (2016).
31. Jessica Alba (2006 cover — without consent)

Source: UGC
- Nationality: American
Jessica Alba, born April 28, 1981, appeared on Playboy's 2006 cover through photographs used without her consent. Hugh Hefner issued a personal apology to Alba after the unauthorised use of her image. Jessica accepted the apology.
Alba has been a vocal advocate for personal rights and brand control throughout her career. She went on to co-found The Honest Company, a consumer goods business, and has been consistently listed among Hollywood's most commercially successful actresses.
32. Paris Hilton (2005 cover — without approval)

Source: UGC
- Nationality: American
Paris Hilton, born February 17, 1981, appeared on Playboy's 2005 cover through images used without her formal approval. The matter was ultimately not pursued legally, largely because of Paris Hilton's existing friendship with Hugh Hefner.
Hilton was one of the most photographed celebrities of the mid-2000s, and the Playboy incident reflected the era's loose boundaries around celebrity image rights.
33. Azealia Banks (2015 photo shoot)

Source: UGC
- Nationality: American
Azealia Banks, born May 31, 1991, appeared in a Playboy photo shoot in 2015. The Harlem-born rapper had signed to XL Recordings at age 18 and is known for her provocative public persona as much as her music.
Her Playboy appearance was consistent with a career built on unapologetic self-expression and boundary-pushing imagery.
34. Kim Kardashian (December 2007 issue)

Source: UGC
- Nationality: American
Kim Kardashian, born October 21, 1980, appeared in Playboy's December 2007 issue, featuring an unclothed pictorial. She also appeared on the cover of Playboy's Romanian edition.
Kardashian has since become one of the most recognisable figures in global celebrity culture, building a multi-billion-dollar business empire through her SKIMS and SKKN brands.
35. Denise Matthews — Vanity (April 1988)

Source: UGC
- Nationality: Canadian
Denise Matthews, known professionally as Vanity, was born on September 4, 1959, and appeared in Playboy's April 1988 issue. She was the lead singer of Prince's protégée group Vanity 6.
Matthews died on February 15, 2016, aged 57. She had stepped back from entertainment in the 1990s following a religious conversion. Her Playboy appearance is one of the more notable documents of her pre-conversion celebrity era.
36. Barbara Carrera (two appearances — 1977 and 1982)

Source: UGC
- Nationality: American
Barbara Carrera, born December 31, 1945, appeared in Playboy twice — in July 1977 and March 1982. She had previously modelled for Vogue and Harper's Bazaar, and became one of the few models to appear in Playboy across two separate decades.
Carrera is also known for her acting career, including her role as the villain Fatima Blush in the James Bond film Never Say Never Again (1983).
37. Farrah Fawcett (two appearances — 1995 and 1997)

Source: UGC
- Nationality: American
Farrah Fawcett, born February 2, 1947, appeared in Playboy twice: a semi-unclothed shoot in December 1995, and a full pictorial in July 1997 — the latter released when she was 50 years old and one of the magazine's top-selling issues of that year.
Fawcett, a Charlie's Angels star and Emmy and Golden Globe nominee, died on June 25, 2009, aged 62.
38. Diora Baird (August 2005 cover)

Source: UGC
- Nationality: American
Diora Baird, born April 6, 1983, appeared on Playboy's August 2005 cover. She was signed to Elite Model Management at the time of her appearance and used the Playboy platform as a springboard into acting.
Baird has since worked steadily in film and television, though her Playboy cover remains her most widely recognised public appearance.
39. Tricia Helfer (February 2007 cover)

Source: UGC
- Nationality: Canadian
Tricia Helfer, born April 11, 1974, appeared on Playboy's February 2007 cover. She is best known for playing Number Six in the acclaimed science-fiction series Battlestar Galactica (2004–2009).
Helfer's Playboy appearance coincided with the peak of Battlestar Galactica's cultural impact, drawing significant attention to both the show and the magazine.
40. Kiana Tom (May 2002 cover)

Source: UGC
- Nationality: American
Kiana Tom, born March 14, 1965, appeared in Playboy in May 2002. She was best known at the time for hosting Kiana Tom's Flex Appeal on ESPN, a fitness programme that ran through the 1990s.
Her Playboy appearance was unusual for a sports television presenter of her profile and drew attention to the magazine's broad appeal across entertainment genres.
41. Charisma Carpenter (June 2004 cover)

Source: UGC
- Nationality: American
Charisma Carpenter, born July 23, 1970, appeared in Playboy's June 2004 issue in a ten-page unclothed pictorial. She is best known for playing Cordelia Chase in Buffy the Vampire Slayer and its spin-off Angel.
Carpenter's Playboy appearance attracted a large audience from the Buffy fanbase and was one of the magazine's more notable celebrity issues of the mid-2000s.
42. Aubrey O'Day (March 2009 cover)

Source: UGC
- Nationality: American
Aubrey O'Day, born February 11, 1984, appeared in Playboy's March 2009 issue. She rose to fame as a member of the girl group Danity Kane, which was formed on Making the Band 3.
O'Day has remained a fixture in celebrity media through her music and reality television work, and her Playboy appearance came during the period of her greatest mainstream visibility.
43. Garcelle Beauvais (Featured at age 40)

Source: UGC
- Nationality: Haitian-American
Garcelle Beauvais, born November 26, 1966, appeared in Playboy at the age of 40 — an unusual distinction in an industry that typically favours younger models. She is best known for playing Fancy Monroe in The Jamie Foxx Show (1996–2001).
Beauvais has since become a co-host of The Real daytime talk show and a cast member of The Real Housewives of Beverly Hills, maintaining a high public profile well into her fifties.
44. Nicole "Coco" Austin (March 2008 cover)

Source: UGC
- Nationality: American
Nicole Austin, known professionally as Coco, was born Nicole Natalie Marrow on March 17, 1979. She appeared in Playboy's March 2008 issue and had previously worked at the Playboy Mansion from 2001.
Austin is also known as the wife of rapper and actor Ice-T, with whom she stars in the reality series Ice Loves Coco.
45. Sherilyn Fenn (December 1990 cover)

Source: UGC
- Nationality: American
Sherilyn Fenn, born February 1, 1965, appeared in Playboy's December 1990 issue. She is best known for playing Audrey Horne in David Lynch's cult television series Twin Peaks.
Fenn received Emmy and Golden Globe nominations for her Twin Peaks performance, making her one of the most critically acclaimed actresses to appear in Playboy during the 1990s.
FAQs
- Who was the first celebrity to pose for Playboy? When Playboy was first published in 1953, the inaugural issue featured unclothed photographs of Marilyn Monroe.
- Who was the last celebrity to pose for Playboy? Pamela Anderson, the 2015 Playboy cover model, was the last person to pose unclothed for the magazine, closing a more than 60-year tradition.
- Who was the last Playboy Playmate of the Year winner? Jordan Emanuel was the last Playmate of the Year in 2019. The magazine stopped crowning its models the Playmate of the Year title afterwards. Playboy ended its print edition with the Spring 2020 issue before transitioning to a digital-first model.
- How much do celebrities get paid to pose for Playboy? The magazine typically pays its models more than the standard $25,000, and celebrities who pose unclothed are paid hundreds of thousands to millions of US dollars.
- Who was the highest-paid Playboy model? No official figure has been published for the single highest-paid Playboy model. Celebrity appearances command fees far above the standard $25,000 Playmate rate, with some reportedly receiving millions. Anna Nicole Smith, Jenny McCarthy, and Pamela Anderson are among the Playmates who received the most significant paydays, each earning at least the $100,000 Playmate of the Year prize in addition to their shoot fees.

Source: Original
Conclusion
Beautiful women have graced Playboy magazine's pages since its first issue in 1953, with some winning the Playboy Playmate of the Month or Year titles. The models became symbols of beauty, sensuality, and empowerment as their photos inspired generations of women to embrace their forms of self-expression.
We also highlighted facts about 25 iconic 80s models who reshaped fashion and beauty, from Cindy Crawford and Iman to Naomi Campbell and Elle Macpherson.
Their influence reached far beyond the runway: these models became pop-culture stars, broke barriers, and helped define the supermodel era—a legacy still visible in fashion today.
Source: Legit.ng
