Taylor Rain first entered the porn industry in November 2001. By October 2003, she estimated that she had shot between 200-250 scenes. She signed an exclusive two-year performing contract with Legend Video, which would allow her to cut back on the number of scenes she shot and provided her a private chauffeur so that she could arrive at her sets in a timely manner. However, Legend released her from her contract less than a month later, and she considered retirement. She took a short break from performing around that time.

In August 2004, she signed a non-exclusive promotional contract with Astrux Entertainment. Then in 2005, she made her directorial debut with the 1st Strike Films release Ass Up Face Down, in which she also starred. In the same year, she signed a contract with Defiance Films and Torrid Entertainment and auctioned a day with herself on set, on eBay for US $3,900.

Taylor Rain was the winner of the "Porn Star Beauty Pageant" on the Howard Stern Radio Show in March 2005, beating out fellow porn stars Kami Andrews, Railee, Renee Pornero, and Aurora Snow.

In December 2005, Taylor Rain announced her retirement from acting in porn movies. When announcing her retirement, she also expressed her desire to settle down and start a family. Despite her retirement, Defiance Films extended her contract for two years. She launched her website, clubtaylorain.com in June 2006.

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