Drew Barrymore

Born in 1975, Drew Barrymore is a 44 year old American actress, author, director, model and producer. She is a descendent of the famous Barrymore family that has multiple members who became A-list Hollywood actors and accomplished stage and Broadway actors as well. Key figures in the Barrymore family include; John Barrymore (her grandpa), Dolores Costello (her grandma), Lionel Barrymore (her great uncle), and Ethel Barrymore (her great aunt). Drew’s godmother was the iconic actress Sophia Loren and her godfather is notable director Steven Spielberg. Drew started her acting career when she was just 11 months old starring in a dog food commercial. During the audition the dog nipped her and Drew just laughed, so they gave her the part. In 1982, she played Gertie in E.T. The Extra-Terrestrial which became her breakout role. She has been starring in films ever since. She also wrote an auto biography when she was 16 about her childhood, which was marked with alcohol and drug abuse. She’s modeled for companies like Guess. She’s also directed films (Whip it) and produced under her film company, Flower Films.

In the 90’s, when Drew was a teenager she made her image be the bad-girl seductive type. She starred in films like Poison Ivy and Guncrazy to help solidify this image. She posed nude for Playboy when she was just 19 years old. On her next birthday her godfather Steven Spielberg gave her a quilt with a note that read “cover up.” She would go on to be on 10 covers for Playboy in ten countries ranging from Japan to Russia.

Madonna

Born in 1958, Madonna is an American pop singer, songwriter, and actress. She is referred as the “Queen of Pop” in the industry. She has sold more than 300 million units making her the most successful female solo artist of all time by the Guinness Book of World Records. She is also the highest grossing solo touring artist of all time, having made around $1.4 billion in concert ticket sales. Madonna also branched out into acting in films; such as Evita, A League of their Own, Dick Tracy and Desperately Seeking Susan.

Madonna has appeared on a total of 11 covers for Playboy. Her covers have been in ten different countries, including multiple in Spain. Her 1985 American cover shot coincided with her marriage to the actor Sean Penn and her film Desperately Seeking Susan.

Paris Hilton

Born in 1981, Paris Hilton is a 38 year old model, actress, singer, DJ, realty tv star and socialite. Paris is the great-granddaughter of Conrad Hilton, who owns the Hilton Hotel chain. Paris is accredited to reviving “famous for being famous” in the early 2000’s, which is a phenomenon that happens when a person basically becomes famous for being rich and pretty. She became an international star in 2003 when her reality tv show The Simple Life came out weeks after a sex tape of her was leaked. Paris’ persona on screen was the dumb rich pretty blonde. Despite portraying being dumb, Paris actually had an amazing career in many fields; writing, modeling, music, acting, even DJ’ing.

Paris was on only 2 Playboy covers, one in America and one in Slovakia. Her 2005 American cover shot coincided with her new film coming out, House of Wax and the release of her new book Your Heiress Diary: Confess it all to Me.

Charlize Theron

Born in 1975, Charlize Theron is a 44 year old South African actress and producer. She rose to prominence in the 90’s for her roles in the films; The Devil’s Advocate, Mighty Joe Young and The Cider House Rules. In 2003 she won an Oscar for portraying a serial killer in the movie, Monster. She also produced the film too. She has been in several top-grossing box office hits like Hancock, Prometheus, Mad Max, Fury Road, The Fate of the Furious and Atomic Blonde.

Charlize Theron has appeared on the cover of Playboy a total of 3 times. Both in the United States and Japan. Her 1999 cover shot coincided with her film, The Cider House Rules, which she was nominated for a Screen Actors Guild Award.

Pamela Anderson

Born in 1967, Pamela Anderson is a 52 year old Canadian-American model and actress. Her career kicked off when she was chosen in 1990 for the Playboy’s February issue Playmate of the Month. A year later she was casted as Lisa on the tv show Home Improvement, starring Tim Allen, which she played for two seasons. Soon after, Anderson became an international sex-symbol for her role as C.J. Parker in the famous life guard series, Bay Watch. She then acted in Hollywood films like Raw Justice, Barb Wire, and Blonde and Blonder.

Pamela Anderson has been on 151 covers for Playboy in 31 countries around the world. She holds the world record for most featured Playboy Playmate. Her first cover was in 1989 after she got a little fame from starring in a series of beer commercials.

Carmen Electra

Born in 1972, Carmen Electra, who’s real name is Tara Leigh Patrick, is a 47 year old American actress, model, dancer and singer. In 1991, Carmen moved to Minneapolis, Minnesota. One month later she met Prince and was signed to his record label as a singer where he produced her debut album. This is when she decided to change her name to Carmen Electra. Her musical career was short lived, but years later she would go on to sing and dance in collaboration with The Pussycat Dolls. Carmen moved to LA and started getting bit roles in tv shows. In 1996 she modeled for Playboy and got on the cover. This got her some positive attention from Hollywood and she got the role as Lani McKenzie on Bay Watch. In 1997, she made her film debut in the horror movie American Vampire. She went on to be featured in many comedies and parody movies like, Scary Movie, Date Movie, Good Burger, Epic Movie, Disaster Movie and Meet the Spartans.

Carmen Electra has been on 44 Playboy covers in 21 different countries. From 2000-2009 she was on the US version three times. Her cover shot in 1996 helped her land an acting gig on Bay Watch, which became an insanely popular show and got her famous.

Jessica Alba

Born in 1981, Jessica Alba is a 38 year old American actress and business woman. When she was 11 years old she convinced her mother to take her to an acting competition where the first prize was free acting lessons. Jessica won the prize and 9 months later an acting agent signed her. She made her film debut at just 13 in the movie, Camp Nowhere. Then she appeared on the tv series, The Secret World of Alex Mack. Her career really took off when she was casted as the lead character in James Cameron’s tv series Dark Angel in 2000, when she was 19 years old. This opened the door to her starring in big blockbuster Hollywood movies like; Fantastic Four, Fantastic Four: Rise of the Silver Surfer, Good Luck Chuck, Sin City, Machete and Spy Kids: All the Time in the World. Jessica also founded her own business called The Honest Company that sells household, baby and personal products.

Jessica Alba appeared on a Playboy magazine one time in 2006. Though it was on both the US and Japanese version. Playboy named her on their “25 hottest celebrities” list, so they featured her on the cover by taking a promotional picture she took for marketing her newest film, Into the Blue. When Jessica saw it she filed a lawsuit against Playboy for using her photo without her consent. She didn’t want people to think she had nude photos inside the magazine. Hugh Hefner wrote an apology note himself and offered to donate money to some of Jessica’s favorite charities. She ended up dropping the lawsuit.

Lindsey Lohan

Born in 1986, Lindsey Lohan is a 33 year old American actress, producer, model, singer-songwriter, Fashion designer and business woman. Lohan was signed to Ford Models as a child and starred in over 60 commercials by the time she was 10. At 10 she acted on the soap opera, Another World. She was on the show for only a year because she was casted as the lead in Disney’s 1998 remake of The Parent Trap, which her performance made her an international star. Lohan starred in more movies, her most well known are probably, Freaky Friday and Mean Girls. Lohan also pursued a career as a singer and put out two albums that went Gold and Platinum. Lohan owns several businesses, including night clubs in Greece.

Lindsey Lohan appeared on the Playboy cover in 2012 in five different countries. Her cover shot was inspired by Marilyn’s Monroe’s cover shot that appeared on the very first Playboy issue. This magazine issue that featured Lindsey’s picture on the front broke sales records.

Marilyn Monroe

Born in 1926, Marilyn Monroe was an American actress, model and singer. She is best known for being one of the world’s most popular sex symbols and an American cultural icon. She became a Hollywood star portraying the “blonde bombshell” in comedic films. She was typecast as the sexy and naive dumb blonde, though later in her career she proved to be a good dramatic actor as well. Monroe got her start when she was discovered in a factory producing goods for the war effort. She modeled for factory promos and secured a successful pin up model contract before she became a Hollywood star.

Marilyn Monroe has appeared on 22 covers for Playboy, ranging in 13 countries, but only one being while she was still alive. She was on the very first issue in 1953. It helped jump start her Hollywood career.

Kim Kardashian

Born in 1980, Kim Kardashian is a 38 year old reality tv star, social media star, actress, model, businesswoman and socialite. She first became known because she was the daughter of Robert Kardashian, who was O.J.’s defense attorney in his murder case. She was also Paris Hilton’s friend and personal stylist. Kim appeared in four episodes of Paris’ reality tv show, The Simple Life. Kim Kardashian became better known when a sex tape of her and her boyfriend, the singer Ray J, was released in 2007. Later that year, the network E! started filming a new reality series about Kim and her family called Keeping Up With the Kardashians. This became one of the most successful reality tv shows ever and spawned a few spin off series.

Throughout the years Kim has amassed hundreds of millions of followers across her social media accounts, making her one of the most recognizable names in the world. She married the rapper Kanye West in 2014 and so far they have had 4 children together. He has also acted in movies, Disaster Movie, Death in the Valley and Temptation; Confessions of a Marriage Counselor.

In 2007, Kim Kardashian appeared in a cover shot for Playboy in nine different countries. It followed the premiere of her new reality tv series, Keeping Up With the Kardashians. The photoshoot was in one of the episodes.

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