10. Catherine DeneuveOne of the best-respected actresses in the French film industry, Catherine Deneuve made her reputation playing a series of beautiful ice maidens for directors. She was first featured in Playboy in 1963 at the age of 20, and went on to be pictured in the magazine more than a dozen times over the next several years.
9. Anna Nicole Smith
After an attention-grabbing debut as cover girl of the March 1992 Playboy, she made the Centerfold two months later. Signing her Data Sheet as Vickie Smith and claiming to weigh 140 pounds, Miss May listed a bold ambition: "I want to be the new Marilyn Monroe." Well, this as Anna Nicole Smith.
8. Cindy Crawford
She was ranked number 5 on Playboy's list of the 100 Sexiest Stars of the 20th century.Crawford was named one of the 50 Most Beautiful People by People magazine. She continues to provide celebrity endorsement for a variety of projects and was featured as #26 in the 2006 Hot 100 issue of Maxim magazine.
7. Jenny McCarthy
Born in Chicago, Illinois, to a middle-class Irish American Catholic family, was the MVP of her high school softball and field hockey teams.
She was playboy playmate of the month in October of 1993 and then Playmate of the Year in 1994.
6. Drew Barrymore
As the granddaughter of the great John Barrymore, Hollywood connections were never a problem for Drew. Her godfather is Stephen Spielberg and her godmother is Sophia Loren. Made a career comeback playing a teenage seductress in Poison Ivy, and posing nude for the January 1995 issue of Playboy.
5. Jayne Mansfield
Famed for her platinum-blonde hair, dramatic hourglass figure, and breast-baring costumes, she emerged during the 1950s appetite for well-endowed sex symbols led by Marilyn Monroe.Jayne Marie Mansfield was a Playboy centerfold in the magazine's July 1976 issue.
4. Bo Derek
Derek started out as a model, after she needed to make some quick money to buy a surf board. Later turned into actress, Derek became a sex symbol in the B-movies. Throughout the 1980s, she appeared nude in numerous issues of Playboy Magazine.
3. Ursula Andress
Ursula Andress is somewhere in the Top 5. Maybe her icy distance will always be responsible for not reaching numero uno. Born in Berne, Switzerland, on March 19th, 1936, recently turned 71, Ursula Andress was more often than not faking at being an actress, which didn't bother her the least. Plunged by fate in that kind of living, she used the fame as an excuse to meet numerous famous men.
2. Marilyn Monroe
Probably the most celebrated of all actresses. She posed nude for the now famous calendar shot which was later to appear in Playboy magazine in 1953 and further boost her career. She would be the first centerfold in that magazine's long and illustrious history.
1. Pamela Anderson
Pamela Anderson is a gorgeous Canadian model/actress with beautiful American cleavage. She has posed in playboy five times and been in three different hit TV shows, including the über-popular Baywatch. She is considered one of the most beautiful people in the world.
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