15 Stars Who Nailed Gender Bending Roles

4. Jeffrey Tambour

Jeffrey Tambour is currently playing a 70-year-old transgender woman in the Amazon original series Transparent. The critically acclaimed dramedy centers around Mort who decides to start living as Maura and the changes that this makes on his own life as well as his relationships with his children and family members. Jeffrey has said: “I’d say that, without a doubt, this is the most transformative role that I have ever done.”

5. Felicity Huffman

In Transamerica, Felicity Huffman took on the role of a transgender man about to take the final step towards becoming a woman. She ends up on a literal journey across the country with the son she never knew she had, and ends up getting to know him at the same time that she is getting to know herself. She earned an Oscar nomination for the role in 2006.

6. Neil Patrick Harris

Neil Patrick Harris took a gender bending role to the stage when he played an East German transgender glam rock singer in Broadway’s Hedwig and the Angry Inch. Neil has been openly gay since 2006. He admitted that the role was a challenging one. “Hedwig is bringing up a lot of super insecure things within me. I have never thought drag was intoxicating, I’ve never had a fun drunken Halloween in drag, never been in heels, really. I’ve lived my whole life being attracted by masculinity — it’s why I like guys. I’m not a super effete person, and I have to turn into that, and in doing so it brings up a lot of homophobic insecurities within myself.”