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Her mother died of skin cancer on February 20, 1976, when Jenna was two years old, after which she became very close to her brother, Tony Massoli.During her childhood, she took ballet classes, which helped her future career as a stripper, and was a frequent entrant in beauty pageants.After only a few films, she quickly achieved notice and critical success, and in 1996 won top awards from three major industry organizations, the X-Rated Critics Organization Best New Starlet, the AVN Best New Starlet, and the F. By 2001, she earned ,000 for a day and a half of filming a single DVD, and tried to restrict herself to five films per year, and dancing at strip clubs two weeks per month, earning ,000 per night.Since November 2005, she has been the host of Playboy TV's Jenna's American Sex Star, where prospective porn stars compete in sexual performances for a contract with her company.They lived together at the start of her porn career and again in 2000.

She was soon earning 00 per night, before finishing high school.She does claim that she sometimes watches the acting portions, but will fast-forward through the sex.On December 20, 1996, Jameson married porn star Brad Armstrong.His name, "Jay", was tattooed on her left ring finger.They unsuccessfully tried to have children since mid-2004.

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