From the moment Marilyn Monroe appeared on the first-ever cover in December 1953, the hottest Playboy models have set the standard for American pop culture beauty. Pamela Anderson holds the all-time record with 13 covers. Kim Kardashian’s December 2007 issue was one of the best-selling magazines of the entire 21st century. And every decade since has produced a new generation of Playmates who turned their bunny ears into multi-million-dollar careers.

Playboy stopped printing its monthly magazine in March 2020, and 2019’s Jordan Emanuel was the last individual Playmate of the Year (all 12 of 2020’s centerfolds shared the title in the magazine’s farewell run). But the legacy of the top Playboy Playmates only grew. The Netflix Pam & Tommy series, the Holly Madison podcast, and Carmen Electra’s record-breaking OnlyFans launch have all kept the brand and its biggest names firmly in the cultural spotlight in 2026.

Below are the 12 sexiest Playboy models of all time, ranked by cultural impact, magazine history, and what they have built since. These are the names that defined the magazine and the women who built empires after it. For more iconic women in entertainment, browse our list of the hottest blonde Instagram models.

12 Best Playboy Models to Watch

1. Marilyn Monroe (@marilynmonroe)

The original. Marilyn Monroe graced the first-ever cover of Playboy in December 1953, an issue that effectively launched the magazine and minted her status as the global blonde bombshell of the 20th century. The photos were taken before her fame, which made the issue an instant collector’s item the moment it hit newsstands.

Decades after her death in 1962, she remains the most iconic of all famous Playboy models. Her estate is active across Instagram and licensing deals, and her image is still the touchstone every later Playmate has been measured against.

2. Pamela Anderson (@pamelaanderson)

The all-time queen. Pamela Anderson appeared on a record 13 Playboy covers between 1990 and 2016, more than any other model in the magazine’s history. Her first cover in October 1989 catapulted her to Home Improvement, then Baywatch, and into a level of fame that few Playboy Playmates have ever matched.

The 2022 Netflix Pam & Tommy series and her own 2023 Netflix documentary brought her into the cultural conversation all over again. She now uses her platform for animal rights activism and her cookbook, and her Instagram crosses over with some of the highest-engagement Instagram bikini models on the platform.

3. Jenny McCarthy (@jennymccarthy)

Hugh Hefner selected Jenny McCarthy out of 10,000 applicants for her October 1993 cover because of what he called her “wholesome Catholic girl” look. She was named Playmate of the Year in 1994, then turned that platform into MTV’s Singled Out and an entire television career.

Jenny McCarthy has appeared on six Playboy covers across two decades and is now a co-host on The Masked Singer, a New York Times bestselling author, and one of the most outspoken voices in autism advocacy. She is the textbook case of a Playmate who built a real second-act career.

4. Anna Nicole Smith (Legacy)

Anna Nicole Smith first appeared in Playboy in March 1992, then was named Playmate of the Year in 1993. The Texan model became one of the magazine’s most enduring symbols of 90s glamour, with Guess campaigns, magazine covers, and her own reality show all flowing from that single cover.

Her life was filled with both fame and tragedy, and she passed away in 2007 at age 39. Her legacy still sits firmly in the top tier of sexy Playboy models, and her image is one of the most reposted on every “best of Playboy” Instagram fan account.

5. Kim Kardashian (@kimkardashian)

Kim Kardashian’s December 2007 cover was one of the best-selling Playboy issues of the entire 21st century. The shoot was famously documented inside Keeping Up with the Kardashians, and at the time it served as a public reclamation of her image.

Nearly two decades later, she runs SKIMS (valued at over four billion dollars), sits at 360M+ Instagram followers, and remains one of the highest-paid Instagram influencers on the planet. The Playboy cover was a pivot point in a career that has only kept compounding.

6. Carmen Electra (@carmenelectra)

Carmen Electra appeared in Playboy in 1996, 2000, and 2003, with her Baywatch fame and MTV hosting career running parallel to the covers. She effectively became the face of late-90s American sex symbol culture alongside Pamela Anderson.

In 2023 she launched her own OnlyFans, which broke platform launch records and pulled in over a million dollars in its first month. She remains one of the most active and most-followed famous Playboy models in 2026, with a content business that out-earns her acting career.

7. Cara Delevingne (@caradelevingne)

Cara Delevingne covered Playboy in 2017 in a striking shoot that marked a major moment for the magazine’s modern rebrand. She was the British supermodel and Burberry face who became a Hollywood actress, and the Playboy issue was a deliberately edgy creative statement from both sides.

With 44M Instagram followers, she remains one of the most followed female Instagram models in fashion. Her acting credits include Suicide Squad, Carnival Row, and Only Murders in the Building, which keeps her in the cultural conversation year after year.

8. Charlize Theron (@charlizeafrica)

Charlize Theron’s May 1999 Playboy cover came at the peak of her transition from model to leading lady, just two years before her Oscar nomination for The Cider House Rules and four years before she won the Academy Award for Monster. The South African-American star treated the cover as a fashion editorial.

She has since founded her own production company, Denver and Delilah Productions, headlined the Mad Max and Atomic Blonde franchises, and remains one of the few celebrity Playboy models who has won both a Playboy cover and a Best Actress Oscar.

9. Sara Jean Underwood (@saraunderwood)

Sara Jean Underwood was Playmate of the Month in July 2006 and Playmate of the Year in 2007. She is one of the most successful Playmates of the post-print era, with a 9 million-plus Instagram following built around her van-life and outdoor photography content.

Her aesthetic blends Pacific Northwest landscape photography with her own modeling, and her grid is one of the most copied templates on Instagram. She is the proof point for what a top Playboy Playmate career can look like in the social media era.

10. Holly Madison (@hollymadison)

Holly Madison was the most recognizable face of the Playboy Mansion era, headlining The Girls Next Door alongside Bridget Marquardt and Kendra Wilkinson. She lived at the mansion as Hugh Hefner’s “main girlfriend” from 2001 to 2008.

Madison has since released two New York Times bestselling memoirs (Down the Rabbit Hole and The Vegas Diaries), launched a popular podcast on the dark side of the mansion years, and remains one of the most quoted voices in the post-Hefner conversation. She is the historian of the Hottest Playboy era.

11. Lindsey Vonn (@lindseyvonn)

Lindsey Vonn covered Playboy in April 2017, an issue that broke from the magazine’s tradition by featuring one of the greatest American athletes of all time. The Olympic gold medalist and four-time World Cup overall champion is the most decorated female alpine skier in US history.

She uses her 2M-plus Instagram for fitness, philanthropy, and behind-the-scenes ski content. Her Playboy cover is also one of the magazine’s strongest examples of the rebrand toward female athletes and creators rather than just traditional model casting.

12. Dita Von Teese (@ditavonteese)

Dita Von Teese earned her December 2002 Playboy cover after years of building a burlesque career that single-handedly revived the genre. The magazine famously misspelled her name as Von Teese on the cover, which she liked enough to keep permanently.

She is now the most famous burlesque performer in the world, the founder of Dita Von Teese Beauty, and a permanent fashion week front-row fixture. Her aesthetic, retro pin-up with high-fashion polish, is one of the most copied looks on Instagram in 2026.

Why Playboy Models Still Dominate Pop Culture in 2026

Print Playboy ended in March 2020, but the cultural value of being a Playmate has only grown. The 2022 Pam & Tommy series, Holly Madison’s runaway podcast, Carmen Electra’s record-setting OnlyFans launch, and Pamela Anderson’s two-part Netflix series all reignited demand for the hottest Playmates of all time.

The brand also pivoted hard into creator economy infrastructure. Playboy Centerfold launched as a subscription content platform in 2022 that competes directly with OnlyFans, and many former Playmates are now running their own creator businesses on it. The new economic model rewards the original Playboy bench more than the print magazine ever did.

For brands looking to scout creators with this kind of legacy reach, tools like Ainfluencer’s influencer search platform help filter by audience and engagement, and brand ambassador programs are the right structure for long-term partnerships with established names.

Conclusion

From Marilyn Monroe’s 1953 debut to Kim Kardashian’s 2007 reset to Lindsey Vonn’s 2017 athlete-cover moment, the 12 women on this list defined what Playboy meant across seven decades. Each of them used the magazine as a launchpad and built something significantly bigger on the other side.

If your interest pulls toward more current creator-economy talent, our roundups on nude Instagram models and YouTubers with OnlyFans are the next logical reads. These 12 names are the foundation that every modern adult creator brand is built on.

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