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She tried to follow in her mother's career as a Las Vegas showgirl, but most shows rejected her for not having the then-typical height of 5 feet 8 inches (173 cm). According to E!, her brother Tony, who later owned a tattoo parlor himself, added the inscription "Heart Breaker".
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Jack was a tattoo artist and gave her the first of a series of tattoos, one of which would become her trademark tattoo, two hearts on her right buttock. Rather than tell her father, she left home and moved in with Jack in her first serious relationship. Preacher has denied the rape ever occurred. She reported being raped a second time while still 16 by "Preacher", her boyfriend Jack's biker uncle. The incident began after she attempted to hitchhike home and that she entered the car of the four boys while believing that she would be driven to her home. Jameson wrote in her autobiography that in October 1990, when she was 16 years old and while the family was living on a cattle ranch in Fromberg, Montana, she was beaten with rocks and gang raped by four boys after a football game at Fromberg High School. In a featurette on the Zombie Strippers DVD, Jameson indicates she trained in dance for fifteen years. Jameson was a frequent entrant in beauty pageants as a child and enrolled in ballet classes throughout her childhood. She and her older brother Tony were raised Catholic, though they were essentially left to parent each other. The cancer treatments bankrupted the family and they relocated in Nevada, Arizona and Montana, usually living in a trailer home or with her paternal grandmother. Her mother died of melanoma on February 20, 1976, two months before her daughter's second birthday. Her mother, Judith Brooke Hunt, was a Las Vegas showgirl who danced in the Folies Bergère show at the Tropicana Resort & Casino. Her father, Laurence Henry Massoli, was a police officer at the Las Vegas Sheriff's Department and program director for KSNV-DT. Jenna Marie Massoli was born on April 9, 1974, in Las Vegas, Nevada.
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Her 2004 autobiography, How to Make Love Like a Porn Star: A Cautionary Tale, spent six weeks on The New York Times Best Seller list.
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Playboy TV hosted her Jenna's American Sex Star reality show, in which aspiring porn stars competed for a ClubJenna contract.
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Her mainstream appearances continued with several guest-hosting and guest-starring on various television programs. Jameson has also crossed over into mainstream pop culture, starting with a minor role in Howard Stern's 1997 film Private Parts.
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By 2005, ClubJenna had revenues of US$30 million with profits estimated at half that. The first such movie, Briana Loves Jenna (with Briana Banks), was named at the 2003 AVN Awards as the best-selling and best-renting pornographic title for 2002. Initially, a single website, this business expanded into managing similar websites of other stars and began producing sexually explicit videos in 2001. Jameson founded the adult-entertainment company ClubJenna in 2000 with Jay Grdina, whom she later married and divorced. She has since won more than 35 adult-video awards, and has been inducted into the X-Rated Critics Organization (XRCO) and Adult Video News (AVN) Halls of Fame.
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By 1996, she had won the "Top Newcomer" award from each of the three major adult movie organizations. She started acting in erotic videos in 1993 after having worked as a stripper and glamour model. She has been named the world's most famous adult entertainment performer and "The Queen of Porn". Jenna Marie Massoli (born April 9, 1974), known professionally as Jenna Jameson ( / ˈ dʒ eɪ m ə s ə n/), is an American model, former pornographic film actress, businesswoman, and television personality.