Rain first entered the pornographic video industry in November 2001. In 2003, she signed an exclusive two-year performing contract with Legend Video which would allow her to cut back on the number of scenes she performed in and provided her a private chauffeur. Legend released her from her contract less than a month later, and she considered retirement, but instead only took a brief hiatus from performing.
In August 2004, she signed a non-exclusive promotional contract with Astrux Entertainment.
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 her on set on eBay for $3,900.
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.
Off screen, Rain won control over Scott Fayner's porn industry gossip site Lukeford.com.
In December 2005, Rain announced her retirement from acting in pornographic movies, expressing a desire to settle down and start a family. Despite her retirement, Defiance Films extended her contract for two years. She launched her website, clubtaylorrain.com, after retiring.
In June 2006, she announced via her website that she was pregnant, but miscarried one month later.