Oct 27, 2021

Top 50 Sexiest Celebs Who Posed For Playboy – 2020

Playboy magazine is one of the top notch entertainment and lifestyle magazines in the world. They are better known for their bold shoots and branded as a Men’s magazine. Their covers and pages have been adorned by some of the best in the business. Hence, it becomes a statement of success for those who get the opportunity to be featured in the Playboy.

Over the years, it has grown to be a trend that the hottest of men and women pose for this magazine. Here, we have compiled a list of top 50 sexiest celebs who got themselves featured in this popular magazine.

1. Cindy Margolis

Cindy Margolis is a popular American fashion model and she has also worked as an actress in some projects. She is best known for her perfect features and her glowing skin. The blonde-beauty got the opportunity to be a part of the Playboy magazine and she has starred in several movies as well.

She was a consistent poser for Playboy but she never posed naked for them. Cindy starred in movies such as Chairman of the Board and Dead Above Ground. She had her talk show, endorsed products like Reebok, and worked in several television shows such as Beverly Hills Nannies and Bad Publicity.

2. Lisa Rinna

Lisa Rinna is the perfect example of aging gracefully and currently, even at the age of 56, she is as graceful as ever. She was quite a diva back in the day and was known for her desirable features and stunning looks. She worked as an actress and was a popular face on television.

Besides her stint with Playboy, she worked on projects such as The Real Housewives of Beverly Hills, Dancing with the Stars, and many others. She has been a part of numerous projects that have been praised for their content and currently, she has her line of products as well in the markets.

3. Stacey Dash

We know her best for being an attractive talk-show host and an actress. Stacey Dash has also turned heads with the bold poses that she struck for playboy. She boasts of shine in her eyes and her beautiful brown skin pays the perfect homage to her beauty.

She is mostly seen in short hair cuts that suit her face. Stacey has been in television roles such as CSI: Crime Scene Investigation, Celebrity Circus, and Single Ladies. She has also been in some popular music videos like for the one she shot with Kayne West. Her work with Fox News also made her a popular face.

4. Anna Nicole Smith

This busty beauty has not only featured in the Playboy but has also earned the Playmate of the Year title in the year 1993. She is none other than Anna Nicole Smith and as a popular plus-size model, she worked with several brands. She was an attractive blonde and worked out hard to keep herself in perfect shape.

Her associations included some of the best brands in the business such as H&M and Guess. She worked with Lane Bryant and Heatherette as well and has put in some of her best efforts till her unfortunate demise at the age of 39.

5. Tara Reid

You probably know Tara Reid from her popular appearance in the American comedy films like American Pie, American Pie 2, and American Reunion. Her flowing locks of blonde hair complement her innocent beauty. With her amazing features, she strikes quite a pose which was evident when she made the headlines after posing for the Playboy magazine.

She has been a very successful actress and her work in movies such as Van Wilder, My Boss’s Daughter, Alone in the Dark, and Urban Legend deserve special mention. She is an asset to the American film industry with her skillful acting.

6. Cindy Crawford

Cindy Crawford is a popular supermodel and her work in some diverse projects has earned her a lot of name and fame. She is best known for her impeccable looks and the way she carries herself. Her poses ooze confidence and it was no exception during her bold shoot with the famed Playboy magazine.

She has also worked in a few movies such as Fair Game, The Simian Line, and many others. The world also admires her numerous fitness videos and she is an inspiration on how to stay in shape even at the age of 54.

7. Jesse Jane

Jesse Jane is the stage name of the popular adult film actress Cindy Taylor. She is known for her sensational beauty and her features which have perfection stamped all over it. Her flowing blonde hair, her mesmerizing eyes, and her dressing sense combine to make her one of the most desired porn actresses. Besides a successful career in the porn industry, she has also featured in numerous magazines including her famed Playboy appearance. She is known for her sexy attires and the way she carries herself in style.

8. Jaime Pressly

The sitcom My Name is Earl earned Jaime Pressly a permanent place in the hearts of her fans. She was also loved for her astounding beauty and incredibly attractive features. Everything about her from her golden locks to her innocent smile is capable of making men weak in their knees.

She also worked in movies such as Joe Dirt, Not Another Teen Movie, A Haunted House 2, and numerous other projects. The TV series Mom also sees some of her finest works. Her appearance in Playboy was another feather in her cap that has been illustrated with numerous other achievements.

9. Jessica Hall

You may know Jessica Hall for her famous feature in the Playboy magazine but she has been quite a diva and worked in numerous roles. She has been an actress and a popular personality on television. Jessica Hall has a divine signature smile. It is in perfect harmony with her remarkable beauty and her talent.

She has also been the host for the Playboy Radio Show and as of now, she organizes this Happy Hour on the Sirius/XM 102. This beautiful personality is a must-mention in this list of the sexiest women on Playboy.

10. Crista Flanagan

She is one of the healthier beauties in the glamour world and her work is a reflection of the body-positivity that has been around in the recent past. She is of course, the famous actress and comedian Christa Flanagan.

Besides her talent, she is known for being an extremely desirable lady equipped with stunning looks. Her physique is appropriate to put together a great photoshoot and for this reason, she has worked for several modeling assignments including her stint with Playboy. Christa Flanagan is the dream come true for thousands of her male fans all over the world.

11. Barbi Benton

Barbi Benton may have retired from modeling now but back in the day, she was quite a sensation. She was a part of many acting and modeling assignments but the world knew her best for her modeling skills. She was a great singer as well and appeared in the popular Playboy magazine.

It was an appearance that made her fans drool over her attractive physique. She worked in a comedy series titled Hee Haw and she was also a part of many albums where she put up a brilliant musical performance. Her youthful appearance and glittering perfect eyes made her a truly dreamy character.

12. Jayne Mansfield

Among the numerous American actresses who made an impact with their attractive presence, Jayne Mansfield is a prominent name. She was a part of some of the best movies back in the day and also managed to establish herself as a sex symbol in the 1950s and 1960s.

Her appearance in the Playboy magazine was a regular event back then and she even earned the Playboy Playmate title for her work. Her silver blonde hair and her hour glass figure made Jayne Mansfield a favorite among her fans. She was also a part of movies such as Too Hot to Handle, The Wayward Bus, Illegal, Kiss Them for Me, and many others.

13. Raquel Welch

This American beauty managed to steal the hearts of her fans with her powerful screen presence. She is best known for her works as an actress, but Raquel Welch is also a capable singer. She has been hailed as a stunning beauty for her impeccable features. A look at her in her prime was enough to leave you hypnotized in her dazzling beauty.

She had the perfect smile and stood tall and combined her features with some brilliant performances. Besides her stint with Playboy, she starred in movies such as Bedazzled, 100 Rifles, Hannie Caulder, and several others including her works on television.

14. Bo Derek

Bo Derek has set the screens on fire with her presence in some of the hottest fantasy films ever made. She was also a part of the popular sex comedy named 10. She was a popular sex symbol for her work and was a desirable celebrity back in the day.

Some of her movies such as Tarzan, The Ape Man, Bolero, and Fantasies are a fine exhibition of her sensuality. This aspect of her personality was further indulged in by Playboy who featured her for several shoots. The blonde beauty with beautiful eyes and confidence, adorned the magazine on many occasions.

15. Farrah Fawcett

She has been a stunning beauty but her achievements ensured that she was a lot more than just an attractive face in Hollywood. The American beauty Farrah Fawcett starred in several roles that earned her prestigious award nominations such as the Golden Globe Awards for which she was nominated six times.

Her wavy blonde hair, toned physique, and her charming presence made her a favorite among her fans and her admirers for her Playboy stint. She worked in the TV series Charlie’s Angels and was cast in movies such as Cannonball Run, Love is a Funny Thing, Saturn 3, Sunburn, and many others.

16. Geri Halliwell

Geri Halliwell, they say, stares deep into your soul, such is her powerful gaze. She is known for being an attractive lady who has enjoyed a significant amount of success for her numerous roles on TV and movies.

However, she is best known for her musical talents and her first album called Schizophonic was extremely popular among her fans. She followed up her successful work with several hit singles such as Calling and Scream If You Wanna Go Faster. This attractive woman was a part of the Playboy shoot as well and her feature in the magazine was loved and admired by thousands of her male fans.

17. Charlize Theron

She is a great beauty who also enjoys the honor of winning the Academy Awards and the Golden Globe Awards for her acting performances. Her sharp features and petite physique make men fall for her by the drop of a hat.

She has ruled the hearts with performances in super-hit movies such as The Devil’s Advocate, The Cider House Rules, Mighty Joe Young, and several others. She also modeled for several brands courtesy of her perfect appearance and during her stint with the Playboy magazine, she made quite a fortune. Her fans also loved her confident poses for this magazine.

18. Naomi Campbell

Her beautiful brown skin makes her one of the most attractive African-English models. She worked her way up the ladder after an early start to her career. Naomi Campbell has worked with numerous big names in the fashion world including the Playboy magazine shoot.

She does not shy away from bold shoots and her tall stature and perfect features make her an attractive presence for the magazines. Naomi Campbell has been hailed by many as one of the best models of her generation and going by the volume and the quality of work that she has been able to complete, it is no exaggeration.

19. Kiana Tom

She is one of those women who can steal your hearts with her fitness oozing from her presence. Through hard work and discipline, the beautiful Kiana Tom has made her way up the ladder to become one of the hottest television hosts in America. It is thus no surprise that Kiana Tom was selected by Playboy to be a part of their magazine shoot.

Besides this, she has been known widely for her work in Kiana’s Flex Appeal which aired on the ESPN network. She hosted some of the biggest shows such as the ABC Super Bowl Nightlife and other hit shows. She was a part of films as well and movies like Universal Soldier: The Return, did justice to her talent.

20. Kristy Swanson

Her blonde hair and her graceful screen presence make Kristy Swanson loved by her millions of admirers. She has been a part of some iconic movies such as Buffy the Vampire Slayer.

She has also worked in the movie The Phantom. Through her remarkable acting performances and extremely sexy looks she has managed to hog the limelight for the better part of her career. Her appearance in the Playboy photo shoot only established her talented personality even further.

21. Dita Von Teese

The name Dita Von Teese brings about a fond memory for many of her fans over the years. That memory is her appearance in the Playboy magazine when this graceful beauty set the magazine on fire with her stunning shoot.

She was also hailed for great dancer and fashion designer. Her modeling stint improved with each passing day as she was hailed as the Queen of Burlesque for her performances. Dita Von Teese has some remarkable features such as her stylish black hair, her glorious smile, and her perfectly sculpted features. She is not just a great model but also an individual who pays a great deal of attention to her physique.

22. Tia Carrere

Tia Carrere could smile and take your breath away such is the power of her incredible beauty. The tanned beauty has been known for being a great model and actress and over the years she established herself as a very attractive woman. Even now, at the age of 53, she stands graceful and beautiful as ever.

Besides her work with the Playboy group, she was cast in the popular show General Hospital. Tia was also a part of other hits on TV such as True Lies, Dancing with the Stars, The Celebrity Apprentice, and many others.

23. Daryl Hannah

The busty blonde Daryl Harper has ruled the hearts of her fans for a considerable amount of time. During her prime, Daryl Hannah was known for her powerful screen-presence and her beautiful appearance. Her flowing locks of long hair complemented her dreamy eyes and her toned physique was in perfect harmony.

She has been a part of some prominent movies like The Fury, Blade runner, Summer Lovers, Splash, and many others. Her stardom and her attractive appearance meant that she was soon roped in by Playboy for a shoot. She did not disappoint her fans and during her appearance, she turned quite a few heads through some jaw-dropping poses.

24. Rachel Hunter

The bright and glowing gaze through the beautiful eyes of Rachel Hunter pierces the heart and strikes a chord. Her perfect petite physique and her attractive presence ensure that this model and actress is sought after by several brands and projects. She has worked for magazines such as Vogue and Elle as well besides the Playboy project that roped her in.

She was also a popular model for magazines like Sports Illustrated and Harper’s Bazaar. Her fans eagerly awaited her appearances as this bold and beautiful model never ceased to entertain them. She starred in movies like Piranhaconda and Her Infidelity which were popular among her fans.

25. Kim Basinger

Kim Basinger maybe 66 years old as of now but back in the day, she was one of the most popular actresses in America. This blonde-haired and blue-eyed beauty was also a part of numerous modeling assignments which ensured that she ruled the hearts of her male fans.

Kim Basinger posed for the Playboy magazine and also worked in popular films such as From Here to Eternity, Hard Country, and many others. Her work as a Bond-girl in the movie Never Say Never Again sealed the deal and she was officially one of the most attractive sex-symbols of her time.

26. Joan Collins

She is a veteran of several films as of now but once upon a time Joan Collins could kill with her curves. She had the desirable hourglass shape and her perfectly shaped face was a great combination together with her physique. One of her special performances can be observed in the soap opera named Dynasty. For this role, she won the Golden Globe Awards as well. She acted brilliantly in some of her other movies such as The Woman’s Angle, Cosh Boy, Turn the Key Softly, and Our Girl Friday. Due to her looks, she was a great asset to the fashion world as well and was a regular for several brands.

27. Goldie Hawn

She could synthesize grace with sensuality and that made Goldie Hawn an extremely desirable character. She was a part of hit sitcoms such as Rowan & Martin’s Laugh-In which made her a popular name in the American household.

She was also the winner of the Academy Award and Golden Globe Award which put all doubts on her acting skills to rest. She won these awards for her role in Cactus Flower. She was picture-perfect and a sight for sore eyes and it is no surprise that Playboy roped her in to be a part of their shoot.

28. Madonna

Madonna is possibly the biggest name in the world of female pop artists of all time. She is hailed as the queen of pop and this tall blonde has features to die for. Back in her prime, her perfectly toned physique was the cause for stirring up the press and she scorched the magazines on several occasions with her sensuous presence.

She brought out a signature tone in herself through some of her albums such as True Blue and Like a Virgin. Her melodious voice in songs like Take a Bow, Hung Up, Frozen, and her age-defying beauty has made Madonna such a diva and an icon.

29. Brooke Shields

She is known for her killer curves and the busty beauty Brooke Shields has been an amazing actress as well. Some of her greatest assets are her incredible smile and her toned physique for which she puts in a lot of hard work.

She has been in movies such as Endless Love, The Blue Lagoon, and her performance on the television hit Suddenly won her Golden Globe Award nominations as well. Brooke Shields has been the face for several popular fashion magazines and for those who are glued to television shows, she is a huge name. The Playboy appearance earned her a separate fan-base who was admirers of her modeling work.

30. Mariah Carey

She has some gifted features such as her innocent smile and her five-octave vocal range. This meant that this pop singer was a combination of a melodious voice and incredible beauty. She is known for her busty physique and her voluptuous body has featured in numerous famous fashion magazines.

She has been the singer for some very popular singles such as Emotions and Vision of Love and is hailed as one of the highest-selling music artists. With so much talent compiled into one, Mariah Carey is undoubtedly a highly sought-after artist.

31. Vanna White

Television personalities are also often extremely popular for their attractive presence and Vanna White is no exception. This blonde beauty, endowed with sharp features and a petite physique has ruled the television for quite some time.

She is best known for being the host of the show named Wheel of Fortune and this tall and lanky beauty has also been a successful model. Among her several modeling assignments, she also posed for the famous Playboy magazine and the shoot left her fans drooling for her.

32. Vanity

She is known for her multiple hairstyles and while she sometimes posed with an afro, at other times she maintained straight hair. She hailed from Canada and impressed with her acting and musical skills. She is best known for being the lead performer of the girl group named Vanity.

Her beautiful eyes and her melodious voice together make for the perfect recipe to steal hearts and it is no surprise and she was one of the most desirable women back in the day. She also worked with Playboy courtesy of her fame and together they made for quite an edition full of her sultry pictures.

33. La Toya Jackson

She hails from the famous Jackson family and she too established herself as a singer. However, for La Toya Jackson, it was much beyond just her amazing voice. She was a delightful beautiful back in the day with her unique hairstyles. Her expressive eyes spoke a million words and she is best known for her work in singles such as Heart Don’t Lie.

She was incredibly famous for her work in songs such as You’re Gonna Need My Lovin If You Feel the Funk and many other chartbusters. Her graceful appearance was truly a sight to behold and she was a special Playboy girl.

34. Sharon Stone

Nobody can forget the sex-symbol Sharon Stone who left a deep impact with her audiences through some of her acting performances. Best known for her role in Basic Instinct, Sharon Stone boasted of the perfect physique with her curves winning hearts.

She was, however, an amazing actress as well and some of her performances won her the Golden Globe Award and Academy Award nominations. She acted in several other films such as King Solomon’s Mines, Action Jackson, Cold Steel, and Above the Law.

35. Sherilyn Fenn

She embraced the world of acting and glamour with her graceful and smart looks. Her lively smile, her stunning eyes, and her perfect physique ensured that Sherilyn Fenn was a huge hit with the audiences.

She is best known for some remarkable performances in roles such as Boxing Helena, Wild at Heart, and the hilarious performance in Rude Awakening which was a popular sitcom. This 55-year-old is still quite a graceful presence and has not lost much of her youthful beauty.

36. Elle Macpherson

Australia is known for some of the most desirable models and Elle Macpherson is one among them. Besides being a television host, she is known for being a great actress and has managed to strike up a business of her own. She is known for her hourglass figure and her stunning eyes that are sure to mesmerize you.

Elle Macpherson has been a popular television host as well and as a model, she was a common feature in fashion magazines such as Vogue, Sports Illustrated, and many others. Her work with Playboy made her even more popular as she stuck some remarkable poses during this stint.

37. Robin Givens

Robin Givens is one of the few African-American models who have managed to impress on the larger stage. She has also worked in some films and television projects in the course of her long career. She is known for her unique looks toned physique makes her a great sight for sore eyes.

She has been involved with some popular television hits such as The Women of Brewster Place and Boomerang. Her other roles that entertained the audiences are The Game, Riverdale, and several others. Her work with Playboy is appreciated by the fashion world for the sultry photo-shoot that made the news.

38. Pamela Anderson

You hear the name Pamela Anderson and you immediately think of the show Baywatch that was her claim to fame. The blonde beauty is known for her curvy and busty appearance. She was a sex-symbol and popular among fans for some amazing performances in Home Improvement, V.I.P, and of course the unforgettable bold shoot with the Playboy magazine.

She was also cast in some movies such as Barb Wire, Raw Justice, and Blonde and Blonder, and in all her roles, her raw sensuous quotient was exploited by the filmmakers to rope in the audiences in large numbers.

39. Drew Barrymore

She has been a showstopper ever since she stepped foot into the world of glamour and acting. The blonde beauty has a smile to take your breath away and her innocent face is beautifully equipped with the most attractive pair of eyes.

She has worked with several brands courtesy of her gorgeous looks but she is best known for being the winner of the Golden Globe Award and her BAFTA Award nomination. Drew Barrymore has performed exceptionally well in movies such as E.T. the Extra-Terrestrial, Boys on the Side, Mad Love, Scream, Poison Ivy, and many other remarkable roles.

40. Charisma Carpenter

She shot to prominence with the series titled Buffy the Vampire Slayer but Charisma Carpenter has a separate fan base that admires her out-of-the-world beauty. She has beautiful brown eyes to complement her innocent smile and flowing locks of long hair.

She worked in many other interesting projects on television such as The Lying Game and The Expendables film series that is a huge hit. At the age of 49, she still retains her youthful appearance and continues to be a highly sought after actress.

41. Denise Richards

She has been gifted with the perfect physique and well-endowed breasts complementing her slim waist. Denise Richards became a sex-symbol after her appearance in movies such as Wild Things and a James Bond movie titled The World is Not Enough.

She was a showstopper as a Bond-girl and was also in the news for her relationship with Hollywood heartthrob Charlie Sheen. Denise has been involved with numerous modeling assignments including the one with Playboy where she put up a great display of the perfect poses. She is now 49 years old although she is still capable of turning quite a few heads with her sexy personality.

42. Jenny McCarthy

Jenny McCarthy is a loved American actress and beside her acting skills, she is hailed as one of the prettiest in the industry. She has one of the finest sets of blonde hair and her pretty face breaks into a divine smile which is a dream for the photographers.

She has worked as a model and has been a successful TV host as well. She posed nude for the Playboy magazine and even eared the title of Playmate of the Year. She has been a part of movies such as Scream 3, Diamonds, Santa Baby, and hit TV shows like Singled Out. She might be 47 years old but there are no signs of aging to show for.

43. Teri Polo

She is a sensational model and actress and this American beauty has been known to pull off a short-haired style for the better part of her career. She carries herself gracefully and her curves make sure that she looks desirable in every pose.

Teri Polo has worked in TV hits such as The West Wing, The Fosters, Good Trouble, and many other popular roles. She has been a top-model and has been associated with some of the finest brands in the business. Her stint with Playboy added further fuel to the fire of her desirability quotient and she was quite a star for her bold shoots.

44. Paris Hilton

The socialite Paris Hilton is best known for her blond flowing hair and her petite physique. She has been a successful model and businesswoman who also tried her hand at acting and fashion designing. One of the best features of Paris Hilton is her heavenly smile and witty personality.

She was a part of the reality TV show named The Simple Life and besides this, worked on numerous modeling assignments. Paris Hilton posed for the Playboy magazine and it was extremely popular among the readers of this magazine who drooled over her incredible beauty on display.

45. Bai Ling

Not many American-Chinese actresses made as much of a name for themselves as Bai Ling. She has been a popular model and a perfect specimen of the ideal Asian beauty. She is known for her petite frame and endowed curves and as a result, she is the best of both worlds.

Bai Ling has been involved with movies such as Red Corner, The Crow, Wild Wild West, Anna and the King, and many other interesting projects. Her work with Playboy is mesmerizing, to say the least as she struck one bold pose after another in the course of her featuring in this popular magazine.

46. Tricia Helfer

She might be a popular Canadian actress but Tricia Helfer is regarded very highly as an attractive lady. She earned this tag due to her exceptionally perfect facial features.

She has also been involved with several modeling assignments such as the one with Battlestar Galactica on TV. The popular FOX series titled Lucifer saw her essaying a crucial role with ease. Tricia Helfer has been winning hearts ever since she stepped into the glamour world and even today, it is no exception with growing popularity for this star with every passing day.

47. Anna Faris

If Anna Farish could not impress you with her looks, nobody could. She has been involved with numerous roles as a fine specimen of American acting. She mostly aced comic roles with her incredible comic timing and her performance has been praised from all quarters.

Her innocent beauty has been appreciated in movies such as May, Hot Chick, Lost in Translation, Brokeback Mountains, and many other remarkable roles. She also starred in movies such as The Dictator, The House Bunny, and What’s Your Number.

48. Carmen Electra

She has been a sensational name when it comes to the glamour world and as a model and actress she established herself like no other. Her incredible good looks are coupled with the hourglass shape that makes her an extremely desirable personality.

Besides posing for the Playboy magazine, Carmen has been a part of several other projects such as Baywatch which was a huge hit on TV. She also starred in the popular MTV show named Singled Out. For her remarkable performances, she is still in the limelight at the age of 48 and carries herself gracefully as ever.

49. Aubrey O Day

She might be a popular American singer and songwriter but she is best known by her fans for her voluptuous and attractive appearance. This blonde-beauty has been a part of the girl band named Danity Kane and has been one of the stars of the fashion world as well.

Owing to her perfect features, she earned a name for herself for being a sensational model. This led to several projects from prominent names in the fashion world and in some time her work with Playboy magazine followed. She was also a part of magazines like Blender and her appeal never ceased to exist for her numerous fans around the world.