Top 8 Must-See MTF Transgender / Crossdressing Movies since 2000

As MTF transgender and crossdressers, we have several movies that depict our lives and challenges accurately. Although the issue of sexuality wasn’t quite explored in movies before, since 2000, directors have been more open-minded in addressing the topic. Here’s a list of the most eye-opening and inspiring crossdresser / transgender movies released in the last two decades.

There are many must-see movies for transgender and MTF crossdressers. For instance, we have movies like “Boys Don’t Cry,” which is based on the real-life story of Teena Brandon, a transgender man who was raped and murdered after his biological gender was revealed. This movie highlights the struggles and challenges that many transgender people go through on a daily basis. Another great movie is “Transamerica” which tells the story of a transgender woman who embarks on a road trip with her long-lost son

In this article, I’ll be discussing 10 of the best transgender movies that have been released in the last two decades. So, without further ado, let’s get started!

1. Danish Girl 2015

Danish Girl is a movie that will definitely stay with you long after the credits have rolled. It is a story of identity, love, and loss told in a way that is both heart-wrenching and gorgeous.

The film follows Lili Elbe (played by Eddie Redmayne), one of the first known recipients of gender confirmation surgery, as she comes to terms with her true self and goes through incredible changes both physically and emotionally.

While Lili’s journey may be unique, her story is one that will resonate with anyone who has ever struggled with their identity. The Danish Girl is a must-see for anyone who is looking for a beautiful, moving portrayal of the transgender experience.

The movie begins with Lili’s wife, Gerda (Alicia Vikander), convincing her to pose for a series of paintings. It quickly becomes apparent that Lili is uncomfortable in her own skin and longs to be something else entirely.

With the support of Gerda, Lili begins to experiment with her appearance and soon decides to live as a woman full-time. This decision comes with challenges, but Lili is finally able to start living authentically.

The Danish Girl is an important film for many reasons. First and foremost, it is one of the few mainstream films that tells the story of a transgender person in a non-exploitative way.

It also does an amazing job of depicting the love and support that is so crucial for anyone going through a gender transition.

If you are looking for a touching, beautifully-made film about the transgender experience, The Danish Girl is definitely worth watching.

2. Transamerica (2005)

Transamerica has been praised as one of the best films about transgender issues in recent years. The film follows Bree, a transgender woman who is about to undergo sexual reassignment surgery. When she learns that she has a son, she sets out on a road trip to meet him for the first time. Along the way, Bree must deal with her own issues of self-acceptance, as well as the prejudices of those around her. Despite all of the challenges, Transamerica is ultimately a heartwarming and uplifting story about family, acceptance, and love.

The movie begins with Bree (played by Felicity Huffman) living as a man named Stanley. She is successful in her career but feels that something is missing in her life. When she learns that she has a son, she decides to go on a road trip to meet him for the first time. Along the way, Bree struggles with her own issues of self-acceptance, as well as the prejudices of those around her. Despite all of the challenges, Transamerica is ultimately a heartwarming and uplifting story about family, acceptance, and love.

If you need a movie that accurately portrays the transgender experience, Transamerica is a must-see. The film deals with complex topics in a sensitive and respectful way and will leave you feeling hopeful and inspired.

2. Kinky Boots (2005)

If you’re looking for a heartwarming and uplifting story about overcoming adversity, look no further than Kinky Boots. This 2005 British comedy-drama tells the tale of Charlie Price, who takes over his family’s struggling shoe factory and comes up with an unlikely solution to save the business: making kinky boots for MtF crossdressers and drag queens!

With a star-studded cast that includes Chiwetel Ejiofor, Joanne Froggatt, and Sarah Jane Potts, Kinky Boots is a feel-good film that celebrates individuality and standing up for what you believe in. It’s also one of the few mainstream movies with a transgender character played by a transgender actress (Rebecca Root), making it an important watch for anyone interested in transgender representation in film.

The movie begins with Charlie (Ejiofor) inheriting his father’s shoe factory in Northampton, England. Struggling to keep the business afloat, Charlie comes up with the idea of making kinky boots for drag queens after meeting one named Lola (played by the fabulous Billy Porter).

Despite initial resistance from his employees, Charlie presses on with his plan and eventually turns the factory around. Kinky Boots is a funny, touching, and inspirational film that will leave you feeling good about yourself and the world around you.

3. Disclosure (2020)

Transgender and crossdressing movies have come a long way since 2000. And Disclosure is one of the stand-out films that transgender and crossdressers must see.

Directed by Sam Feder, Disclosure is a documentary that explores Hollywood’s portrayal of transgender people throughout the years. The film features interviews bearing transgender actors, directors, and producers, including Laverne Cox, Alexandra Billings, Jen Richards, Sean Dorsey, Trace Lysette, Jamie Clayton, and many more.

Disclosure offers an insightful look at how Hollywood has depicted transgender people over the years and how those portrayals have affected the trans community

4. “A Soldier’s Girl” (2003)

A Soldier’s Girl is a 2003 American television film directed by Frank Pierson and based on the true story of the relationship between Pfc. Barry Winchell and his transgender girlfriend, Calpernia Addams.

The film is famous for being one of the first mainstream depictions of a transgender relationship. It is also notable for its frank discussion of the issues faced by transgender people, particularly in the military.

If you’re looking for a realistic and moving portrayal of a transgender relationship, “A Soldier’s Girl” is a must-see.

5. Hedwig and the Angry Inch” (2001)

“Hedwig and the Angry Inch” is a 2001 American musical comedy-drama film directed by John Cameron Mitchell, who also wrote the film. It is based on his own off-Broadway play of the same name from 1998. The film follows Hedwig Robinson (Mitchell), a German rock singer who comes to America as part of a failed relationship with an army private and has to deal with life as a transgender woman.

The movie was met with critical acclaim and is often cited as one of the best films of 2001. It won numerous awards, including the Sundance Grand Jury Prize and Best Director for Mitchell.

If you’re looking for a must-see MTF transgender / crossdressing movie from the past 20 years, “Hedwig and the Angry Inch” is definitely one that should be on your list!

6. Normal” (2003)

If you’re looking for a film that realistically portrays the transgender experience, then “Normal” is a must-see.

The film follows Roy Applewood (played by Tom Wilkinson), a man who has been living as a woman for years, as he comes out to his family and friends. While the film does deal with some heavy subject matter, it ultimately is a feel-good story about accepting yourself for who you are.

“Normal” is one of the few films that accurately depicts what it’s like to be transgender and, as such, is an important watch for anyone looking to better understand the transgender community. If you’re looking for a moving and thought-provoking film about self-acceptance, then “Normal” is a must-see.

7. Boots” (2005)

If you’re looking for a must-see transgender or crossdressing movie from the past few years, “Boots” is definitely one to add to your list.

This 2005 independent film tells the story of Jack, a young man who discovers that he enjoys dressing up in women’s clothing and exploring his feminine side. As he begins to experiment with his newfound interest, Jack also begins to develop feelings for his best friend, Sarah.

Although “Boots” may not be the first movie to explore the transgender experience, it is one of the most realistic and honest portrayals of what it is like to live as a transgendered person. The film does an excellent job of showing both the positive and negative aspects of Jack’s journey and ultimately provides a very moving and inspiring story.

If you’re looking for a film that will challenge your preconceptions about gender and sexuality, “Boots” is definitely a must-see.

So, if you’re looking for a good MTF transgender and crossdressing film to watch, check out any of the movies on this list. You won’t be disappointed! And if I missed your favorite transgender movie, let me know in the comments. I always love hearing from our readers.