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!
Michelle
More Articles by Michelle Liefde
- A Tale of Two Necklaces
- My Journey So Far…
- On Being Michelle and On Being Here
- Media Review: The Music Video for Quiet by Milck
- Media Review: The World According To Garp

Michelle Liefde

Latest posts by Michelle Liefde (see all)
- A Tale of Two Necklaces - September 12, 2022
- My Journey So Far… - July 28, 2022
- On Being Michelle and On Being Here - April 28, 2020
- Media Review: And now for this century… - January 31, 2020
- Media Review: The Music Video for Quiet by Milck - October 4, 2019
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.
xoxo
Daisy
Hi Daisy,
Thank you for commenting. I hope that it inspires all of us in some way. Doing the research and seeing how much more representation is being shown is incredible. Never heard of the Arcade Fire song, just watched the video and wow, pretty powerful. I will be watching it a few more times, I think that Andrew Garfield did a great job. So a good chance that this music video will become an article, thanks for turning me onto it.
Michelle
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 »
Thanks Gwenn! As you know I don’t consider myself a writer but wanting to get information out there is something that does motivate me. I am happy to say I am finding more and more out positive images out there.
Michelle
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 »
Hi Melissa, thank you for commenting and glad you mentioned Ed Wood, Definitely a film that should have been added, so my apologies. I loved that film and am a fan of Wood’s works, even seen a couple that make you shake your head even more than Plan 9. I remember reading Rudolph Grey’s Ed Wood: Nightmare of Ecstasy after seeing the movie. A very interesting and tragic life he lead. As for the Danish Girl, I am hoping to have its own article about the film, and if I don’t get to write it, I hope I get to… Read more »
Thanks Michelle , i haven’t seen any of these , must see some . Thanks for opening our eyes to some interesting media . Love , Leslie
Hi Leslie, thanks for commenting! I hope you enjoy the films. I am hoping to have another article out soon, just working on how to put it together. It looks like it might turn into 2 more. 🙂
Michelle
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 »
Hi Camryn, thanks for the comments and the films mentioned. Will be adding those that to my ever growing list of films. By the way love Boy Meets Girl, too.
Michelle
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.
Cyn
Thanks Cyn! I agree about Stardust. I have loved the story since first reading the Graphic Novel by Neil Gaiman and the beautiful artwork of Charles Vess.
Michelle
Just a quick correction, I mistakenly named the move “Albert Nobbs” as “Alfred Nobbs”. My apologies and thank you to Anne Preuss on TGH for catching it and letting me know. Don’t know how I missed that.
Hugs,
Michelle
No “Angel” from “Rent”? Tsk tsk … (loved the rest tho Michelle!)
Thanks Kristy! Definitely need to add “Rent” to my ever growing spreadsheet.
Hugs,
Michelle
She’s my favorite character — such humanity