Media Review: And now for this century…

It has been close to a year that Captain Dionysus asked me to help work on a project that would give inspiration by reviewing books, films, poems, music, plays, etc. containing Transgender or Crossdressing themes, characters, and actors. As the very first article gave its best attempt at a timeline of sorts since the 2nd World War, I have wondered how to move forward with the past 20 years. So, I am hoping to write 2 articles, this one featuring the first ten years and then from 2010 to present in the second.

For this one I will focus briefly on a collection of movies. So if we start at the beginning of the new century, then let’s start with Boys Don’t Cry (1999), I know it was released in the last year of the century, but the impact it had was still present in early 2000, and Hilary Swank’s acceptance speech for her Oscar, talking of the inspiration of Brandon Teena, the young transman whose the subject of the film, had given her and the those working on the film brings home the point that our stories do matter and can be told and have an effect beyond our community. It seemed to me that mainstream media was finally willing to take a chance on telling stories that were not just the traditional stereotypes.

Or possibly we should start with Hedwig and the Angry Inch (2001) a drama/comedy/musical about the life and love of a fictional transwoman rocker and her gender identity with a pretty decent soundtrack starring John Cameron Mitchell who also wrote and directed the feature as well. Though the film was lauded with acclaim it did not do as well at the box office, but has since become a cult classic to many.  Another film released that year All the Queen’s Men (2001), is a war comedy using the trope of men, including Matt LeBlanc of Friends fame, having to crossdress to accomplish a task and the comedy of them trying to blend in. Hey at least it has Eddie Izzard, a very much out crossdresser, in the film.  Another interesting film that I found was Normal (2003) starring Tom Wilkinson as Roy/Ruth Applewood a husband that decides to transition after 25 years of marriage and the struggles she faces.


In 2005 with release of the comedy Kinky Boots, we have the character of Lola, played by Chiwetel Ejiofor, the drag queen that helps save the day.  Also, there is the critically acclaimed Transamerica (2005) starring Felicity Huffman as Bree Osbourne, a transwoman on a road trip to find her son.  Cillian Murphy starring as Patrick “Kitten” Baden in Breakfast on Pluto (2005), about a young transwoman coming of age in Ireland during the 1970s, and interestingly enough was also searching for someone, in this case her mother.

Other notable A-List actors also would break with traditional gender roles, like Robert De Niro in Stardust (2007) as the crossdressing pirate Captain Shakespeare, who befriends and aids the main characters in their quest.  And Cate Blanchet plays Bob Dylan in I’m Not There (2007), though not a crossdressing role, is still an interesting to see that she had the opportunity to play a male character. Another notable performance is in Albert Nobbs (2011), starring Glenn Close in the title role as woman that presents as a man to work as a butler at a Dublin hotel in the 19th century, who is shy in order to keep her secret going so she can save up enough money to open her own shop. The comedy and drama of the early 2000s were definitely, taking more chances while still producing the traditional stereotypes like White Chicks (2004).

I really wondered if the lack of mainstream Hollywood’s willingness for self-representation on both sides of the camera would change. Of course, there were stories being told in the world of documentaries with the likes A Boy Named Sue (2001) and Southern Comfort (2001) and The Boy I Am (2006) where trans men and women were the subjects with their own voices.  By the way, an article on documentaries would be fantastic, hint, hint.  Another place where things seemed to be making headway is on the “small” screen with trans woman Alexandra Billings being one of the first openly transgender to actually play a trans character on television in Romy and Michelle: In The Beginning (2005).  She has credits on shows like ER and Grey’s Anatomy, and played Davina on Transparent (2014).

Lastly, I know that this article does not cover the scope of what is available out there. Nor did it go into depth.  And that’s where you all come in,  I am hoping that this inspires you to write a review of anything mentioned here or of a poem, film, TV show, play, music video, song that has uplifted you when you were down or where you could relate to the character.  I invite you all to submit your own review, so your voice can be heard and added to our amazing community.

I would like to take a moment and say thank you to all members past and present that have contributed to the Media Review.  With your articles, knowledge, and insight, it would not be as great as it has been.

Much love to all!



En Femme Style


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Michelle Liefde

Hey there, I am Michelle! As an Ambassador to both TGH and CDH, I want to welcome all to this wonderful site! I am still learning who I am and hope to be able to give support to our community.

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3 years ago

I like that this has been written and have been a big film fan for many years. I am familiar with some of the ones listed but it’s been years since watching them. I don’t recall not enough to write a review or make worthy comment. What I will do, is to try and find them to watch and if sucessful write something.

3 years ago

Good luck Michelle, you have quite a task on your hand xx

Josie Jay
Josie Jay(@josiejay)
3 years ago

Hi Michelle. Im doing a paper for my Critical Theory class on the 2015 movie Tangerine. Im using the travails of the trans sex worker Sin-Dee et al, as being representational of the dichotic nature of both patriarchy and capitalism. Trans women suffer horribly by the narrative of those who use patriarchic normality to disrespect them, yet they wish so very much to be a part of this archaic system. The economic aspect from a meta-level examines the decline of the Hollywood area in general in correspondence with the decline of the entertainment industry, especially as it pertains to the… Read more »

Anne Preuss
Active Member
Anne Preuss(@annepreuss)
4 years ago

A correction to your movie list. The title of the Glenn Close movie is not Alfred Nobbs. The correct movie title is “ALBERT Nobbs". My caps only to emphasize the required correction, not intended as yelling 🙂 . I tried to look up Alfred Nobbs in IMDb but found nothing so I had to look up under Glenn Close.
I confess to having seen none of these movies but after reading your article, I am particularly interested to see Boys Don’t Cry and Normal. Thank you.

Anne Preuss
Active Member
Anne Preuss(@annepreuss)
4 years ago

Those English kings of the 9th century will trip you up, every time. 😀

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