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She started acting in erotic videos in 1993 after having worked as a stripper and glamor model.

The site reportedly was profitable in its third week.

The business later diversified into multimedia pornographic entertainment, first by administering other porn stars' websites, then, in 2001, by production of pornographic films.

Her mainstream appearances continued with several guest-hosting and guest-starring on various television programs.

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.

Winners of the contracts for the first two years were Brea Bennett and Roxy Jezel.

In August 2007, Jameson had her breast implants removed, reducing her from a D to a C cup; she also said she was finished with appearing on camera in pornographic films, though she would continue running Club Jenna, which was grossing $30 million per year.

She and her older brother Tony were raised Catholic, In a featurette on the Zombie Strippers DVD, Jameson indicates she trained in dance for fifteen years.

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.

As for picking her permanent professional name, she said, "I had to come up with a good name. So I sat down, opened up the phone book and thumbed to the J's, cause I wanted it to match my first name." She saw 'James', but rejected "Jenna James" because it "sounds too porno".

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".

She said she wanted to get into the business, despite what her agent said.