While gender-bending movies are a niche subgenre, it's slowly gathered up an impressive catalog of films, including Doctor Jekyll, which was released just a few days before Halloween. Films about cross-dressing, drag queens, the transgender community, and even fantasies that involve body-swapping and magical transformations fall into this category.

The best films on this gender-swapping side of cinema are unusual, challenging, and smart. They take on concepts that most films aren't willing to tackle, introducing new ideas and highlighting old prejudices in ways their fans didn't expect.

Updated by Alan A. Mehanna on March 1, 2024: We've updated this list to meet CBR's current publication standard and guidelines.

15 Freak Show Tells the Heartwarming Story of a Genderqueer Teen

With a strong supporting cast that includes Abigail Breslin, AnnaSophia Robb, Bette Midler, and Laverne Cox, Freak Show tells the story of how a proudly flamboyant young gay man overcomes his peers' prejudices by not only becoming a drag queen but also the homecoming queen.

• The film is based on the novel of the same name written by James St. James and was Trudie Styler's directorial debut.

Billy is played well by Alex Lawther and the character is easy to root for. All he wants is to be his most fabulous self and his journey is a joy to watch. Even the film's sadder moments are leading up to Billy getting the happiness he deserves.

14 Zerophilia Understands the Difference Between Gender and Sexual Identity

More of a young adult drama, Zerophilia focuses on a young man who transforms into a woman every time he experiences sensual bliss. Unlike most gender-bending stories, Zerophilia features a more realistic depiction of what would happen if someone swapped genders in an instant.

• The film's opening credits feature a disclaimer from a fake organization created by the filmmakers called "The International Organization of Zerophiliacs."

Luke is understandably unnerved and uncomfortable in the new body, but the more often they become Luca, the more they enjoy being a woman and exploring new feelings. It's an interesting take on the gender-swap concept and manages to introduce some nicely unexpected twists and turns.

13 It's a Boy Girl Thing Offers a Comedic Take on the Body-Swapping Premise

Rather than a serious film showcasing the struggles of gender identity, It's A Boy Girl Thing offers a lighter, more comedic take on the premise. Woody Deane and Nell Bedworth are childhood friends and complete opposites who wake up in each other's bodies after a spell is cast on them during a trip.

• The film features music by Elton John,who also served a the film's executive producer, Ozzy Osbourne, The Black-Eyed Peas, and James Blunt among others.

Through their body-swap, Woody and Nell learn more about and start to understand each other, working past their lifelong differences by the end of the movie. By the end of It's A Boy Girl Thing, Nell and Woody end up in love with each other, and it's a comedic take on learning to understand people from their perspectives.

12 Orlando Shows a Man Restart Life as a Woman

Based on the novel by Virginia Woolf, Orlando focuses on the struggle a man would have if he suddenly woke up as a woman. Tilda Swinton deserves so much credit for her portrayal of an androgynous male who has to start a new life when he transforms into a woman and lives for centuries in his new body.

• Tilda Swinton and Sally Potter began collaborating on the film before the script was even written and decided that they would have the breaking of the fourth wall in the film mirror how Virginia Woolf spoke directly to the reader.

Rather than going for cheap gags, Orlando is a great period drama that treats its concept with sincerity and grace. Adjusting to her new body is a slow process for Orlando, as is confronting the feelings that were dormant in her previous life, but her new body has brought front and center.

11 Gender Identity Is Explored Through Music in Hedwig and the Angry Itch

Protagonist Hedwig is a gay male whose husband-to-be convinces him to have reassignment surgery so they can legally leave the country together. The surgery isn't completed successfully, and the aftermath is explored by Hedwig's band through various songs throughout the movie.

• Before this became a film and a musical, John Cameron Mitchell and Stephen Trask created the character "Hedwig" and Mitchell would perform and tell Hedwig's story between songs. This was the first drag performance with a storyline, live singing, live band, and original songs.

Hedwig and the Angry Itch creatively delves into topics of self-discovery and reuniting with one's other half in order to feel complete. Its musical numbers focus on finding wholeness in one's identity no matter the hardships one faces to get there, and it is a powerful watch for musical fans.

10 Your Name Tries Something Different With Body Swaps

The concept of a man and woman swapping bodies to walk a mile in each other's shoes is clichéd at this point. Your Name, on the other hand, tries something different by having two total strangers switch bodies. Instead of comedic antics as they try to learn to be each other, they both have to learn completely on their own.

• This was the first animated film that was not directed by Hayao Miyazaki to cross $100 million at the box office.

By the end, Mitsuha and Taki learn so much about each other that they develop a genuine love for each other without ever meeting. Your Name can even be tear-jerking at times. The animation is gorgeous and the dual character study is executed well, making the film more than just a novel concept.

9 To Wong Foo Showcases the Beauty Of Drag Queens

There's immediately something enjoyable about seeing action and thriller stars Wesley Snipes, John Leguizamo, and Patrick Swayze play drag queens. It could have been so easy for To Wong Foo to shine a poor light on drag queens, but instead, it's a fun, positive representation of the community.

• To earn his role as Vida Boheme, Patrick Swayze improvised a thirty-minute monologue inspired by the bullying he suffered as a boy studying ballet in Texas.

To Wong Foo's three leads nail their performances as they get into all sorts of misadventures on their road trip. The film also successfully mixes comedy and drama and provides a healthy look into the world of drag queens. In a time when the LGBTQIA+ community was rarely the focus of pop culture, To Wong Foo was a truly forward-thinking film.

8 Victor/Victoria Explores Gender Identity Through a Musical Comedy Lens

Victoria Grant is a struggling British soprano struggling to find work, but everything changes when she's pinned as a male female impersonator by cabaret performer Toddy. Pretending to be a male posing as a female, Victoria finds success, but her view on gender identity becomes twisted and more complicated as time goes on.

• The film was in development in 1978 and was meant to star Dame Julie Andrews alongside Peter Sellers, but Sellers died in 1980 while Andrews and husband Blake Edwards were working on another film, ultimately leading to Robert Preston taking on the role of Toddy when production began.

There's also all the stress that comes with hiding one's true identity in Victor/Victoria, which weighs on Victoria until the movie's conclusion. It's a slapstick musical focusing on LGBT content that deals with serious issues without taking itself too seriously, making for a more lighthearted watch.

7 Freaky Provides a Bloody Twist on a Classic Plot

A slasher villain a lot like the famous Jason Voorhees accidentally swaps bodies with a teenage girl. It's a simple concept but Freaky makes it smart, funny and horrific at the same time. Vince Vaughn is incredibly effective at playing both the Blissfield Butcher and the young woman who's trapped in his gigantic, powerful body, showcasing a wide range throughout the film.

• The film was supposed to have a completely different name initially and was meant to be Freaky Friday the 13th as a nod to Freaky Friday and Friday the 13th.

The same can be said for Kathryn Newton, who ends up stealing the film when she has to portray a killer trying to hide in a high school. Freaky also showcases the pros and cons in both situations, with a killer in a weaker but easily underestimated body, and an inexperienced young woman piloting a massive middle-aged body.

6 The Adventures of Priscilla, Queen of the Desert Is To Wong Foo's Australian Precursor

To Wong Foo... might be more famous than The Adventures Of Priscilla, Queen Of The Desert but this Australian film tackled the concept first. With Guy Pearce, Terence Stamp, and Hugo Weaving turning in strong performances like their To Wong Foo counterparts, this film deserves recognition for its LGBTQIA+ representation and its tender, playful heart.

• The American film To Wong Foo, Thanks for Everything! Julie Newmar, which released after The Adventures Of Priscilla, Queen Of The Desert, has such a similar plot that there were accusations of it being a complete rip-off.

Not only does it feature drag queens, but Terence Stamp's character is a transgender woman. It was rare to find transgender characters, let alone main characters, in this era, not to mention queer people with kids. The filmmakers deserve praise for treating these communities with respect while also delivering a fun road trip adventure.

5 Ma Vie En Rose Depicts One Young Transgender Girl's Struggle With Identity

Young Ludovic struggles with gender identity in the French film Ma vie en rose, desperately wanting to live as a girl while being born male and having their identity rejected by their parents. Ludovic's neighbors are also unsupporting, and Ludovic has to deal with staying true to themselves while facing backlash at every turn.

• Ma Vie En Rose won a Golden Globe Award for Best Foreign Language film in 1998.

The start of Ma vie en rose is especially painful and relatable to those who struggle with gender identity, as Ludovic's private tendency to dress up is originally accepted before their parents realize they truly identify as transgender. Ma vie en rose does a fantastic job of tackling gender and acceptance issues through a child's lens.

4 The Danish Girl Is the True Story of a Transwoman

The Danish Girl is one of the most endearing biopics ever centered on a trans character. What begins as a fun bit of cross-dressing at a party becomes a closeted trans woman's journey of rediscovery and transition. It's eloquently told, showing the long journey transgender women go through, depicting it as both fulfilling and heartbreaking.

• In 2021, actor Eddie Redmayne said that it was a mistake to play a transgender woman in this film and felt a real-life trans woman should have played the part instead.

The Danish Girl showcases the courage it takes to burn important bridges and go through multiple surgeries on the way to becoming the person they are in their hearts. Eddie Redmayne gives a heart-stealing performance in the lead with Alicia Vikander also turning in a memorable performance.

3 Some Like It Hot Is Surprisingly Ahead of Its Time

In the relatively small world of gender-bending movies, Some Like It Hot is the one that crafted the mold for the others, and it shows. It has all the hijinks fans expect when men disguise themselves as women to hide from the mob, and it features a strong performance from Marilyn Monroe as the unforgettable Sugar Kane.

• It took Marilyn Monroe 47 takes to get the line "It's me, Sugar" correct instead of saying "Sugar, it's me."

For 1959, the humor manages to still hold up since it doesn't try to paint crossdressers and drag queens in a bad light. In fact, Some Like It Hot is ahead of its time. One of the leads even start to embrace life as their female persona named Daphne and gets engaged to a man they genuinely like. It's not perfectly balanced or enlightened, but it's smart and funny from start to finish.

2 Breakfast With Scot Tackles the Pressure of Conforming to Gender Norms

Taking on a more comedic tone than other more serious films, Breakfast With Scot tackles the issues of falling outside of gender norms and being forced to conform to them in a more lighthearted manner. Eric and his partner, Sam, become guardians to Sam's brother's stepson, Scot, but they are quickly upset about how Scot chooses to express himself.

• Breakfast With Scot is based on the 1999 novel by the same name written by Michael Downing.

Scot's preference in clothing and hobbies falls outside the typical gender norm for boys, so Eric and Sam try to change Scot's behavior so they can remain closeted. By the end of the film, though, Scot helps teach Eric about love and self-acceptance, and Breakfast With Scot teaches people to be okay with who they truly are.

1 Dr. Jekyll & Sister Hyde Is as Scary as It Is Fascinating

One of the underrated gems in the library of Hammer horror films, Dr. Jekyll & Sister Hyde features a familiar concept, though in this iteration the scientist transforms him into a gorgeous woman. However, instead of the usual comedic hijinks, Sister Hyde fully a horrific story as intriguing as it is thrilling.

• The film is known to not only feature Dr. Jekyll transform into a woman but the film also included Jack the Ripper and two other cases from history intertwined in the plot.

Sister Hyde is more than simply a gender-swapped version of Jekyll & Hyde. It delves deeper into the psychological side of the story, where Jekyll and Hyde's minds meld to the point where they both feature aspects of each other. By the end of the film, both sides can come off as either the victim or the villain, making it difficult to side with either persona.