I stumbled onto the following at : http://trushare.com/88sep02/SE02KIRK.htm

... a  character mentioned at the end of the second letter to Timothy as one who resisted Paul’s preaching – Alexander the Coppersmith – later converted to Christianity, changed sex, and left Ephesus for a new life in Rome. There he altered his name to Phoebe and ultimately became a leading deacon.  The clue which led Baumsterk to this daring conclusion was, he says, the realization of the true significance of the name ‘Phoebe’. ‘Literally, in Greek it means shining one’, the Professor told a crowded press conference, ‘an allusion to Alexander’s former profession.’ But it was also a name for Diana, as goddess of the moon, and so carried a reference to Alexander/Phoebe’s native city. Phoebe, moreover, was the daughter of Uranus who, in mythology, was castrated by his son, Kronos, so alluding to the surgery at the hands of the evangelist and doctor, Luke, who performed the operation at Paul’s request on Alexander’s arrival in Rome.

Make of it what you will, but bare in mind it is written by Rachel Gladraggs, 

"Our Ballroom Dancing Correspondent".

A partial list of trans women (and one man) playing trans in the movies up to 2011

With much justification we complain that trans characters in the movies are usually played by cis actors.  Two recent films that (fortunately) failed to be made, films about Lili Elba and James Barry were both intended to have a cis woman actor playing the trans characters even though Elbe was a woman, and Barry a man. 

There are groups that have this worse than we do.   Apart from Christopher Reeve after his accident, how many disabled characters are played by disabled actors?

This is a short list where trans actors of different types have played trans characters.  I have not included professional gender impersonators here.   A much longer list from Vesta Tilly to Julian Eltinge to RuPaul could be created, but that is not what this list is about.  Nor, with one or two exceptions, does this list include documentaries, nor trans actors in cis roles.

It is no accident that is list is more World Cinema than Hollywood.

Kazuo Hasegaw in Yukinojo Henge (Actor’s Revenge), 1935
Ed Wood in Glen or Glenda, 1952.
Kazuo Hasegaw in Yukinojo Henge (Actor’s Revenge), 1963.
Rachel Harlow, Crystal LaBeija, Sabrina in The Queen, 1968.
Carlotta in The Naked Bunyip, 1970.
Bibiana Fernandez in Cambio de Sexo, 1977.
Jayne County in Jubilee, 1977.
Eva Robin’s in El Transexual, 1977
Angie Stardust in Die Alptraumfrau, 1981.
Angie Stardust, Jayne County, Tara O’Hara in Stadt der Verlorenen Seelen, 1983.
Georgina Beyer in Jewel’s Darl, 1985.
Shelley Mars in Die Jungfrauen-maschine, 1988
Eva Robin’s, Romy Haag in Mascara, 1989.
Alessandra di Sanzo in Mery per sempre, 1989.
Alexis Arquette in Last Exit to Brooklyn, 1989.
International Chrysis in Q & A, 1990.
Doris Fish in Vegas in Space, 1991.
Adele Anderson in Company Business, 1991.
Estelle Asmodelle in Secret Fantasies, 1992.
Ichgola Androgyn, Tima die Goettliche, Ovo Maltine in Ich Bin Meine Eigene Frau, 1992.
Eva Robin’s in Bella al Bar, 1995.
Lady Chablis in Midnight in the Garden of Good and Evil, 1997.
Tima die Goettliche in Der Einstein des Sex, 1999
Antonia San Juan in Todo sobre mi madre, 1999.
Ingrid de Souza in Princesa, 2001.
Lauren Foster in Circuit, 2001.
Kokkorn Benjathikoon in Satree lek (Iron ladies), 2001.
Kokkorn Benjathikoon in Satree lek 2 (Iron ladies 2), 2001.
Florencia de la Vega in Los Roldan, 2004.
Stephanie Michelini in Wild Side, 2004
Alexis Arquette in Lords of Dogtown, 2005.
Bobby Darling in Navarasa, 2005
Raquela Rios in The Amazing Truth About Queen Raquela, 2008.
Lee Na-young in Lady Daddy, 2010.
Yasmin Lee in The Hangover II, 2011.
Harmony Santana in Gun Hill Road, 2011.