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By 1996, she had won the "top newcomer" award from each of the three major adult-movie organizations.
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.
Playboy TV hosted her Jenna's American Sex Star reality show, in which aspiring porn stars competed for a Club Jenna contract. Her father, Laurence Henry Massoli, was a Police officer at the Las Vegas Sheriff's Department and program director for KSNV-DT.
Her mother, Judith Brooke Hunt, was a Las Vegas showgirl who danced in the Folies Bergère show at the Tropicana Resort & Casino.
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.
Of her first adult movie, Randy West said "Jenna contacted me and said she wanted to get into the XXX business, but her agent didn't want her to do porn.
The business later diversified into multimedia pornographic entertainment, first by administering other porn stars' websites, then, in 2001, by production of pornographic films.
Early Club Jenna films starred Jameson herself, limiting herself to on-screen sex with other women or with Grdina, who appeared as Justin Sterling.
I told her if you want to just do a girl/girl scene, we can do that. I figured she'd be the next Ginger Lynn, but nobody had any idea she was going to be as big as she turned out to be. She was the first entertainer to win all three awards. By 2001, Jameson earned ,000 for a day and a half of filming a single DVD, and ,000 per night dancing at strip clubs.
She said she wanted to work with Kylie Ireland, so I set it up. Jenna told me when we first met that she was going to be a star." Jameson's first adult video appearances were lesbian scenes (a common way that female performers ease into the business). Then they offered me lots of money to do boy-girl." When asked about this on The Howard Stern Show on February 8, 2008, she said that she was not necessarily opposed to doing so; rather, "it never really came up", as there were few black men working in porn when she started, and none of them worked [exclusively] for the same company [as] she did. She tried to restrict herself to five films per year and two weeks of dancing per month.
Right under that was 'Jameson' which struck her as being the name of the whiskey she likes and thought "Ok, that's perfect." That night at work she saw her brother and asked him what he thought of the name "Jenna Jameson".