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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.
In 1996, Jameson won top awards from three major industry organizations, the XRCO Best New Starlet award, the AVN Best New Starlet Award, and the Fans of X-Rated Entertainment (F. Between 20, she hosted Playboy TV's Jenna's American Sex Star, where prospective porn stars compete in sexual performances for a contract with her company, Club Jenna.
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 million per year.
He said, "I'm drinking Jameson right now." And the name stuck after that.
She quickly achieved notice and appeared in several other pornographic films while still living in Las Vegas.
On the other hand, he also said that their films took up to twelve days to film, compared with one day for other pornographic films.
In a January 2009 interview with William Shatner on Shatner's Raw Nerve, Jameson said she came close to buying Penthouse magazine when publisher Bob Guccione filed for Chapter 11 reorganization of his business (which occurred in August 2003), but was thwarted when someone else swooped in and bought up all the stock.
A month later I'm on a shoot in Woodland Hills [a San Fernando Valley section of Los Angeles], and there's Jenna.
In 2006, New York City-based Wicked Cow Entertainment started to expand her brand to barware, perfume, handbags, lingerie, and footwear, sold through high end retailers such as Saks Fifth Avenue and Colette boutiques.
In August 2005, Club Jenna launched Club Thrust, an interactive website for Jameson's gay male fans, which includes videos, galleries, sex advice, gossip, and downloads.
She said she wanted to get into the business, despite what her agent said.
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.
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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.