Jenny McCarthy on the Cover of Playboy at 39 -- Plus a Look at the Magazine's Mature Cover Girls

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Actress and model Jenny McCarthy first made a splash in Tinseltown when she graced the pages of Playboy in 1993, nearly twenty years ago. At the time, the 21-year-old blonde bombshell was just starting to make her way in showbiz. She'd eventually land a co-hosting gig on an MTV dating show called "Singled Out," which would help launch Jenny into mega-stardom, where she wound up making several television and film appearances, and even dated funnyman Jim Carrey for a few years.

Now, about five months away from her 40th birthday, McCarthy is back in the pages and on the cover of the most iconic gentleman's magazine in the publishing industry. She told People in an interview that she is "...really proud of it. The pictures are really gorgeous and classy." Ever the cut-up, Jenny added, "It's probably a lot more sophisticated than a lot of the stuff you'd see of people with their clothes on."

Though they have a reputation for filling their pages with pictorials of young 20-somethings, historically Playboy has never been shy to put a more mature lady on their cover or in a photo-spread.

Terry More - Moore is the oldest woman to appear in a pictorial. The "Mighty Joe Young" star was 55 years old when she appeared in the August 1994 issue of Playboy. Moore is still working in Hollywood today, and she's appearing in a horror film, "Mansion of Blood," due out in October.

Nancy Sinatra - Nancy's boots were apparently made for walking into a photo shoot and posing nude. At age 54, Nancy, Frank's daughter and a great singer in her own right, nearly beat out Moore for the top spot when she bared all in the May 1995 issue of the magazine.

Patti Davis - Patti may not be a household name to some, but her father sure was. Former President Ronald Reagan's daughter posed nude in Playboy at age 42. In the July 1994 issue, Davis appeared in a nude pictorial for Hugh Hefner's magazine and last year she appeared in More magazine at the age of 58.

Carol Alt - The term "supermodel" became part of today's lexicon thanks to women like Alt, who was among the first to be given that title. In 2008, the then 48-year-old Carol decided to promote her raw and vegan lifestyle by appearing nude in Playboy.

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