If you loved the coming-of-age charm and heartfelt storytelling of 'Tomboy (1985),' you're in for a treat! This article explores 10 similar movies and shows that capture the same spirit of youthful adventure, self-discovery, and nostalgia. Whether you're a fan of 80s classics or modern tales with similar themes, this list will guide you to your next favorite watch.

Tootsie (1982)
Description: A comedic take on gender roles as an actor disguises himself as a woman to land a role, leading to personal and professional revelations.
Fact: The film was nominated for 10 Academy Awards, including Best Picture.


Victor/Victoria (1982)
Description: Explores themes of gender identity and performance through a woman pretending to be a male drag performer, blending comedy with social commentary.
Fact: The film was adapted from a 1933 German film and later became a successful Broadway musical.


Yentl (1983)
Description: Centers on a woman disguising herself as a man to pursue education and love, highlighting gender roles and societal expectations.
Fact: Barbra Streisand not only starred in but also directed, produced, and co-wrote the screenplay.


The Crying Game (1992)
Description: Delves into complex themes of identity, love, and deception, with a pivotal twist involving gender.
Fact: The film's plot twist was famously kept secret in its marketing campaign.


Orlando (1992)
Description: A visually stunning narrative that follows a nobleman who transforms into a woman, exploring themes of gender fluidity across centuries.
Fact: Based on Virginia Woolf's novel, the film spans over 400 years of history.


The Adventures of Priscilla, Queen of the Desert (1994)
Description: A vibrant road trip movie featuring drag performers, celebrating self-expression and challenging societal norms.
Fact: The film's iconic bus was sold at auction and later restored by fans.


Hedwig and the Angry Inch (2001)
Description: A rock musical that tells the story of a genderqueer East German singer, exploring themes of identity, love, and transformation.
Fact: The film is based on the off-Broadway musical of the same name, which became a cult hit.


Transamerica (2005)
Description: Follows a transgender woman's road trip with her previously unknown son, blending humor with deep emotional resonance.
Fact: Felicity Huffman's performance earned her an Academy Award nomination for Best Actress.


The Danish Girl (2015)
Description: A historical drama about one of the first known recipients of gender confirmation surgery, exploring identity and love.
Fact: The film is inspired by the lives of Danish painters Lili Elbe and Gerda Wegener.


Albert Nobbs (2011)
Description: A poignant story of a woman living as a man in 19th-century Ireland to secure work and safety, touching on themes of identity and survival.
Fact: Glenn Close, who starred in the film, had been trying to bring the story to screen for nearly 30 years.
