Near her high school hometown, in Crawfordsville, Indiana, James attended Wabash College, a liberal arts college for men, where she majored in Latin and Greek and initially planned to teach English. She then attained her Master's degree in English from the University of Chicago.
Beginning in 1996, James underwent a series of facial feminization surgery procedures performed by Douglas Ousterhout, MD. James then posted before and after photographs on her then relatively new TS Roadmap web site and wrote an extensive web diary about her experience, which helped give notability to facial feminization surgery. The facial surgery modified her chin, jaw, nose, forehead, eye bones, and hairline. In 1998, in Portland, Oregon, James received vaginoplasty surgery from Toby Meltzer, MD.
After graduating from college, James worked for nearly a decade at various Chicago advertising agencies, including DDB Worldwide, where she wrote print, radio, and television advertisements for high-profile clients, some of which aired during Super Bowl broadcasts.
In 2003, she co-founded Deep Stealth Productions with her business partner Calpernia Addams, to create educational materials for transsexual women, to raise awareness about the epidemic of violence perpetrated against transpeople and to combat the poor image of transpeople in the media. James is the host of the Deep Stealth Productions instructional film Finding Your Female Voice.
On February 21, 2004, James was a member of the first all-transgender cast, as well as a producer, of The Vagina Monologues, performed on V-Day in Los Angeles. She gave the welcome alongside Calpernia Addams, and performed the monologues "The Woman Who Liked to Make Vaginas Happy" and "They Beat the Girl Out of My Boy - Or So They Tried 04", and took part in the introduction of the Vagina Warriors, along with Addams and Monologues writer Eve Ensler. She has also consulted for the production of a documentary film project about the 2004 V-Day performance entitled Beautiful Daughters and appeared in this film.
James was a script consultant for the 2005 film Transamerica, and also consulted with actress Felicity Huffman for her role in the film. She also made a brief appearance, in an excerpt from her voice video, shown at the opening of the movie.
James appeared in the HBO production Middle Sexes: Redefining He and She, which aired on 6 December 2005.
James appears in the Logo original reality dating television series Transamerican Love Story. She is a confidant to Calpernia Addams as she tries to select from among eight suitors.
She also operates the free TS Roadmap website, a source of information for transsexuals, concerning physical, social, and legal aspects of transition. The section of TS Roadmap on hair removal proved so popular that James spun it off into its own site, Hair Facts, with a companion discussion forum called Hair Tell.
One section of TS Roadmap criticizes the controversial work of psychology professor J. Michael Bailey and of Ray Blanchard and others describing their theory dealing with biology and sexual orientation as scientifically unsound, outdated, and defaming of transsexual people. Bailey denies this characterization of his work and has provided his own account of the controversy.
- Wolfman Productions: Biography of Andrea James. Retrieved on 2007-03-07.
- LesbianAlliance.com interviews DeepStealth's Andrea James. Retrieved on 2007-03-07.
- V-Day: Until the Violence Stops - cast. Retrieved on 2007-03-07.
- Beautiful Daughters at the Internet Movie Database
- Transamerica at the Internet Movie Database
- James, Andrea. Transamerica with Felicity Huffman. Retrieved on 2007-03-07.
- Middle Sexes: Redefining He and She at the Internet Movie Database
- James, Andrea. Categorically wrong? - A Bailey-Blanchard-Lawrence clearinghouse. Retrieved on 2007-03-07.
- Academic McCarthyism. Retrieved on 2007-05-15.
- Andrea's personal site
- Deep Stealth Productions
- TS Roadmap
- Hair Facts
- Andrea James at the Internet Movie Database
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