Sylvester James (1947 – 1988) singer.

Sylvester was raised in Los Angeles. He was encouraged to sing by his grand-mother, the 1920s-1930s jazz singer, Julia Morgan, and he became a child gospel star singing in churches all over southern California and beyond.

However he fell out with his parents and ran away at 16. He lived on the streets in Los Angeles, and moved on to San Francisco in 1967. He performed in drag as Ruby Blue, singing Billie Holliday and the other women blues singers.

He became part of the San Francisco radical drag troupe The Cockettes and is in two of their films, Luminous Procuress and Tricia’s Wedding, both 1971. He also taught them to sing. He also played a female impersonator in the Bette Midler retelling of the life of Janis Joplin, The Rose, 1979.

As a rock singer he had limited success, even though the albums were dance oriented. He found fame as a disco and Hi-NRG singer. He is best known for singing the disco classic "You Make Me Feel (Mighty Real)". Sylvester appeared on the Joan Rivers show in 1986 and talked about his husband Rick, and showed off his wedding ring.

He reacted to pressure from the record label to butch-up his image by attending meetings in drag. He went public when he was diagnosed with AIDS. And attended Pride events in a wheelchair. He died from complications from AIDS at the age of 41. A drag photo-shoot, which he staged as a gag provided the cover for his posthumous album, Immortal, 1989.

• Paul Oremland (dir). The Rhythm Divine: The Story of Disco. US 55 mins 1991.
• David Weissman & Bill Weber (dir). The Cockettes. US 100 mins 2001.
• Tim Smyth (dir). Sylvester: Mighty Real. US 11 mins 2002.
• Joshua Gamson. The Fabulous Sylvester: The Legend, the Music, the 70s in San Francisco. New York: Henry Holt and Co. 2005.
• Kevin E. Taylor. “Sylvester: A revolution recorded, televised & never compromised”. Gay Men of African Descent. www.gmad.org/Sylvester.htm.
• “Sylvester James”. Wikipedia, the free encyclopedia. en.wikipedia.org/wiki/Sylvester_James.
• www.sylstar.net.

Stella MacGregor (192? - ?) bearded lady, accountant.

Betty MacGregor was raised in Battle Creek, Michigan. Even as a young woman she had to shave up to six times a day. She did a master’s degree at the University of Michigan to work with gifted children. While working at the hospital, she she would slip away for a quick shave to avoid funny looks from patients and doctors.


During World War Two she let her beard grow and started working in circus sideshows. She married twice. Her first husband died in the war, and the second died in a road accident. However the demand for bearded ladies had passed, and in the mid-1960s she made only $50 a week.

According to her last manager, she quit the sideshow business, became a man, and he worked as an accountant.

• • Mark Hartzman. “Stella Macgregor” American Sideshow: An Encyclopedia of History’s Most Wondrous and Curiously Strange Performers. Jeremy P. Tarcher/Penguin. 2006: 184-5.

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This is the only case that I have heard of where a bearded lady later becomes a man.

Unfortunately, the manager did not tell Hartzman whether MacGregor's change was aided by hormones and surgery or not.

Carola Kretschmer (1948 - ) musician.

Thomas Kretschmer was born in Fulda, Hesse, West Germany. He became a rock guitarist and worked often with Udo Lindenberg.

Kretschmer transitioned to Carola in 1999. She is still with the Udo Lindenberg band.

• “Carola Kretschmer”. Wikipedia: Die freie Enzyklopädie. de.wikipedia.org/wiki/Carola_Kretschmer.
• www.carola-kretschmer.de/index.html.

Waltraud Schiffels (1944 - ) academic.

Walter Schiffels was born in Saarbrücken, Germany. He did a PhD in German in 1975, and became an instructor at Saarland University, and then Director of Culture Department at Saarbrücken Volkshochschule.

After a divorce from his wife, he became an alcoholic and even worked as a transvestite in a brothel.

She transitioned to Waltraud in 1988. She is also a fiction writer, and has also written an autobiography and advice for transsexuals.

• Barbara Kamprad and Waltrauf Schiffels (ed). Im falschen Körper: Alles über Transsexualität. Zürich: Kreuz Verlag. 1991
• Waltraud Schiffels. Frau werden: Von Walter zu Waltraud. Zürich: eFeF-Verlag. 1992.
• Waltraud Schiffels. Ich bin zwei. Ein Gespräch über Literatur und das Leben zwischen den Geschlechtern. Bamberg: Palette-Verlag. 1993.
• Andrea Bronstering. “Eine Dame alter Schule”. www.transgenderradio.de/beitrag/schiffels.html.
• “Waltraud Schiffels”. Wikipedia: Die freie Enzyklopädie. de.wikipedia.org/wiki/Waltraud_Schiffels.

Synthia Kavanagh (1962 - 2021) sex worker, inmate.

Richard Chaperon was born in British Columbia. From ages 2 to 9 he was in the care of the Children's Aid Society; from age 11 to a week before his 16th birthday, he was in a juvenile detention centre, and first started dressing as female.


Synthia legally changed her name at age 19. As an adult she calculated that she had spent only six years of her life not in some kind of institution.

She says that she always felt that she was female. She has twice been assessed by the Gender Identity Clinics in British Columbia and Ontario, for approval for a sex-change, and has twice been refused.

In 1985, she was working as a prostitute when she murdered a fellow transsexual, her roommate Lisa Black, with a hammer and a knife.

The judge suggested 'simple humanity' requires that Synthia serve her sentence in a woman's prison, however the correctional services rejected this and put her in Millhaven Penitentiary, the maximum-security prison for men in Bath, Ontario. The correctional services would not put her in a women's prison because she still had male genitals, and substantially reduced her dosage of estrogens despite the fact that she has been taking them for many years.

The Clarke Institute of Psychiatry, Ontario's Gender Identity Clinic, refused to approve her for a sex-change because she was unable to complete a two-year Real-Life Test. She filed a human rights complaint and the Human Rights Tribunal agreed that the policy of Corrections Canada placing trans women among the male population was discriminatory and that the absolute ban on sex changes was unwarranted. This decision was upheld in Federal Court.

Kavanagh had the operation in 2000, and in 2001 was transferred to Joliette, a medium-security women’s prison north of Montréal.

In 2005 she trashed a room at Edmonton’s women’s prison and fought off guards. She was then transferred to the maximum-security Grand Valley Institution for Women in Kitchener, Ontario.

• Bruce DeMara. “Serving a life term in two prisons”. The Toronto Star. 4 March 1990.
• “Synthia Kavanagh Human Rights Case”. The Transgender Inmate Experience. Oct 4, 2008. transgenderinmate.blogspot.com/2008/10/blog-post.html.
• Transgender Prisoners in Canada.  http://www.vcn.bc.ca/august10/downloads/trans_prisoners_july2007.pdf

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The 2005 trashing incident provoked some ‘she is still a man’ newspaper articles.

Synthia Kavanagh was not the first Canadian inmate to have gender surgery, although she is the best known.   She was preceded by Shelley Ball in 1980.

Steve Dain (1940 – 2007) gym teacher, FTM pioneer.

Doris Richards attempted marriage as a woman, but it did not work.

Later, while working as a girls’ gym teacher in Union City, California, he transitioned to male at age 35, with surgery from Dr Donald Laub at Stanford Gender identity Clinic.

Steve lost his job and went to court. He was briefly a media topic, but the very next day the Renée Richards story pushed him off the front page.

Eventually he won a court ruling that he could teach again, but was not able to find a school that would hire him.

He worked setting ceramic tiles. He became a focal point for trans men in the San Francisco area, and helped other to follow him including Lou Sullivan, Jamison Green and Max Valerio.

He did eventually teach again in a community college.

He died of cancer at age 67.

• Lee Grant (dir). What Sex Am I? . US 58 mins color 1985.
• Max Wolf Valerio. “RIP Steve Dain – FTM Pioneer”. Trans Group Blog Feb 28, 2008. http://transgroupblog.blogspot.com/2008/02/rip-steve-dain-ftm-pioneer.html.

Eva Robin’s (1958 - ) performer.

Roberto Maurizio Coatti was born in Bologna. He was intersex, who looked like a normal boy, but developed as a woman after puberty.

She took her name from Eva Kent in the Diabolik comics, and Harold Robbins, and thought it to be more cute with an apostrophe.

She is also model and a singer. In 1977, using the name Cassandra, she recorded the disco classic, Disco Panther (see below).

It remains unclear just which intersex condition applies, and there are rumours that she did have genital surgery, perhaps in 1998 or even 1991, although Eva denies this.

She did reveal her penis in the films Evaman, 1980, and Mascara, 1989 (as did Romy Haag), where she played a drag performer, but never since.

In two Hercules films, Ercole, 1983 and Avventure dell'incredibile Ercole, 1984, she played Dedalos as a female, although in Greek myth the character is a man.

She played a transsexual in Belle al Bar, 1994.

She has been in 19 films, and also on Italian television program Il bello delle donne (The Beautiful Women) 2002.

Her legal name is still Roberto Coatti.

•  Annie Richards. “Fabulous Eva”. Second Type Women. www.secondtype.com/gallery-eva.htm.

EN.WIKIPEDIA    IT.WIKIPEDIA   IMDB.