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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 required height of 5 feet 8 inches (173 cm). Her boyfriend Jack encouraged her to apply for jobs as a stripper, and in 1991, though underage, she began dancing in Las Vegas strip clubs using a fake I.D.
Besides dancing, starting later in 1991, she posed for nude photographs for photographer Suze Randall in Los Angeles, with the intention of getting into Penthouse. After her photos had appeared in several men's magazines under various names, she then stopped working for Randall, feeling Randall was "a shark" who had been taking advantage of her.
Jameson says that she started acting in pornographic films to get back at her boyfriend, Jack, for cheating on her. Her first pornographic movie scenes were filmed by Randy West and appeared in 1994's Up and Cummers 10 and Up and Cummers 11. She quickly achieved notice and appeared in several other pornographic films while still living in Las Vegas.
Jameson's first pornographic film appearances were lesbian scenes. She says: "Girl-on-girl was easy and natural. Then they offered me lots of money to do boy-girl." Her first heterosexual scene was in Up and Cummers 11 (1994). At the beginning of her career, she promised herself never to do anal sex or double penetration scenes on film. She has also never done any interracial sex scenes with men.
In 1994, after overcoming her drug addiction by spending several weeks with her father and grandmother, Jameson relocated to Los Angeles to live with Nikki Tyler. She started modeling again, and in 1995 got her father's blessing to make a career out of pornographic films.She started modeling again, and in 1995 got her father's blessing to make a career out of pornographic films.
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, ClubJenna. Winners of the contracts for the first two years were Brea Bennett and Roxy Jezel.
By 2001, Jameson earned $60,000 for a day and a half of filming a single DVD, and $8,000 per night dancing at strip clubs. She tried to restrict herself to five films per year and two weeks of dancing per month. Her husband Jay Grdina has said that she earned as much as $25,000 per night dancing.
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 ClubJenna, which was grossing $30 million per year. In January 2008, Jameson confirmed she is retiring from pornographic performances.