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.

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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!



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Michelle Liefde

When I was young , I loved Deborah Harry. I thought it was just a crush, but realized not only did I find her attractive but what she would wear. When I was 11, I first tried on a dress, pantyhose and bra. I had waited for my family to go out and finally decided to try. We had a storage area in our garage where my mom had some of her old clothes. I would go out there a much as I could. Eventually, I was found out. I buried this part of myself for over 30 years. I spent that time being happy, sad and repressed. Then about 7 years ago, I finally admitted to myself that I wanted to try again. After a little time, I told my wife and luckily she has been growing with me as I figure learn more about Michelle. After the last few years of trying to figure it out, It turns out that I am trans and have decided to transition. I still working out what that means and looks like.

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Daisy Marie
Active Member
3 years ago

Hey Michelle,

Thanks for the thorough list of movies (and the short description of them) you provided through this article. As someone who rarely watch any movie, it’s a perfect to-be-watched list, when there’s anything to do with transgender/crossdressing.

If you don’t know the music clip “We Exist”, made by Arcade Fire, please do watch it and tell us what you think about. It’s sad but true.


Gwenn Liefde
Active Member
3 years ago

Hey Michelle, Great Article! Made me realize how many of those movies I’ve watched and the ones I didn’t. Apparently, I got some catching up to do. hehe. You are absolutely right, there needs to be more movies, books, songs, etc. bringing voice to the CD/Trans community. For movies, I’d like to see more actors/actresses, who they themselves are CD or Trans, acting in those roles. Although I don’t have a problem seeing CIS Actors/Actresses act in those roles, because I think on a personal level for them, it can be eye opening. Not only that, some of the A-Listers… Read more »

Melissa Davis
3 years ago

MIchelle, Apologies if I missed something, but in your earlier piece about the late 20th century I didn’t see a mention of ED WOOD (1994) with Johnny Depp as the eponymous 1950s movie director. As you continue your survey of the 21st century I’m sure you’ll mention THE DANISH GIRL with Eddie Redmayne and Alicia Vikander. Both of those films had a wide audience, unlike THE NEW GIRLFRIEND (2015) by the French director Francois Ozon, whose films often explore gender. It is well worth seeing and is available on Kanopy. The female friend of a man whose wife died shortly… Read more »

Leslies Ann Gray Girl
Leslies Ann Gray Girl
3 years ago

Thanks Michelle , i haven’t seen any of these , must see some . Thanks for opening our eyes to some interesting media . Love , Leslie

Camryn Occasionnel
Active Member
3 years ago

Hi Michelle, I’m not much of a movie critic, and rarely analyze a movie, so I’m hardly qualified to write a movie review. But I am a great fan of CD/TS movies. Of the ones you mentioned, I’ve seen and enjoyed many of them, including “All the Queen’s Men”, “Transamerica”, “Breakfast on Pluto”, and, mentioned by Milissa Davis, “The Danish Girl” and “The New Girlfriend”. I am hoping one day to be able to see the movie “Girl” about a T-girl trying to make it as a ballerina. Also, I hope to see the German romcom “Rubbeldiekatz”, already nearly nine… Read more »

skippy1965 Cynthia
Trusted Member
3 years ago

Great work Michelle. And I highly recommend the movie Stardust you mentioned. Funny yet poignant even though the CD part is kind of a sub plot, It is treated well.

Kristy Bucklyn
3 years ago

No “Angel” from “Rent”? Tsk tsk … (loved the rest tho Michelle!)

Kristy Bucklyn
3 years ago

She’s my favorite character — such humanity

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