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In the last quarter of 1998 she formed her own adult film production company called Jill Kelly Productions. One of the first films out of the company was the 2000 release of "Beautiful" which was directed by Jill and Daisy Chain. Ms. Kelly has a role in the film as well which is a hardcore scene with male costar Julian. In "Coming of Age 1" and "Coming of Age 2", Jill would also have hardcore scenes with Julian and in May of 2000 the couple married. They had a couple of scenes together in the 2001 release of "Immortal" which was directed by Michael Raven. Their marriage wasn't fated to last however and they divorced in August of 2002.
For most of 2003, Jill focused on directing and running her company rather than performing. She directed "Jill Kelly Superstars" that year which featured a lot of award winning stars. "Perfect Pink 17: Pink Matters" was another feature that she produced and directed in that year. "100% Anal 2: Welcome to Jezebelle" was yet another. Although there were several film releases in 2003 that featured her performing, they were all compilations of earlier scenes. In September of 2003, Jill married Corey Jordan who was a fellow director and performer in the adult industry. Their marriage lasted a little over a year and they divorced in October of 2004.
In 2005 her company filed for bankruptcy and the company was bought at auction by Penthouse Media Group for 1.7 million dollars. They outbid Playboy Entertainment Group, New Frontier Media and XGen LLC who were also qualified buyers. The purchase included about 60 unreleased feature films. The sale took place after the bankruptcy filing, Jill's departure and the departure of the remaining contract girls Jenna Haze, Tyra and Nikki Benz. Although it would have been better if the company had been in the black, it was a sale price higher than was expected at the time.