These 15 screen roles span comic disguise, theatrical gender play and portrayals of transgender characters. They are not one interchangeable category: a character hiding their identity for a plot is different from a trans character living as themselves. The selection is subjective, not a definitive ranking; its last entry features two actors.
What “opposite gender roles” means in this list
The phrase is informal. Some characters disguise themselves or perform a role within a role; others are played through drag or deliberate gender ambiguity; two entries portray trans characters. The distinction matters especially for trans roles: a trans person’s gender is their identity, not a disguise or costume.
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The examples below are grouped by the dramatic work gender presentation does in the story, rather than ranked from best to worst.
Comic disguises and roles within roles
1. Robin Williams as Mrs. Doubtfire in Mrs. Doubtfire
Williams plays Daniel Hillard, a father who disguises himself as an older woman to spend time with his children after a divorce. The comedy depends on the contrast between Daniel’s familiar personality and the convincing household persona he constructs as Mrs. Doubtfire.
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2. Dustin Hoffman as Dorothy Michaels in Tootsie
Hoffman plays actor Michael Dorsey, who adopts the identity of Dorothy Michaels to get work. The disguise is also the film’s lens on how women are judged: Hoffman later said that seeing his screen test made him confront his assumptions about women’s beauty standards. In an account of his American Film Institute interview, ABC News reported that Hoffman said, “I went home and started crying, talking to my wife, and I said, ‘I have to make this picture.’” He also described Dorothy as a woman he might have overlooked at a party because she did not meet the physical demands he had been brought up to associate with women he would approach. ABC News, July 11, 2013.
3. John Travolta as Edna Turnblad in Hairspray
Travolta plays Edna, Tracy Turnblad’s mother, in a musical comedy where the role is presented through theatrical performance and costume. Edna is a character in her own right, not a person using a disguise to achieve a plot objective.
4. Eddie Murphy in The Nutty Professor
Murphy plays multiple members of the Klump family, including matriarch Mama Klump. The gender-crossing performance is part of a broader multi-character comic feat, built through shifts in voice, physicality and makeup rather than a single character’s disguise plot.
Rank #2
5. Julie Andrews as Victoria Grant / “Victor” in Victor/Victoria
Andrews plays a woman who performs as a man impersonating a woman. The nested act is central to the comedy: the audience tracks both Victoria’s identity and the stage persona she presents as Victor.
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6. Jack Lemmon and Tony Curtis in Some Like It Hot
Lemmon and Curtis play musicians who disguise themselves as women to escape danger and join an all-female band. Their characters’ efforts to sustain those identities drive the farce. This is one entry featuring a pair of actors.
Drag, theatrical gender play and gender-ambiguous characters
7. Cate Blanchett in I’m Not There
Blanchett portrays one version of Bob Dylan in a film that distributes the musician’s persona across several characters. Her role is not a conventional disguise story; it uses gender-crossing casting as part of a deliberately fragmented, theatrical portrait.
Rank #3
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8. Cillian Murphy as Patrick “Kitten” Braden in Breakfast on Pluto
Murphy plays Kitten, a young Irish person whose self-presentation and search for belonging shape the film. The character should not be reduced to a man in costume: the story follows Kitten’s own identity and life, with gender expression central to the character study.
9. Glenn Close as Albert Nobbs in Albert Nobbs
Close plays a woman who has lived and worked as a man in order to survive in the film’s historical setting. The role is a sustained character study of concealment and the constraints that make it consequential, rather than a comic costume change.
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Swinton plays a character who lives across centuries and changes sex during the story. The film’s gender play is bound up with its meditation on identity and time, not a simple case of one character pretending to be another.
Rank #4
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11. Barbra Streisand as Yentl in Yentl
Streisand plays a young woman who disguises herself as a man to pursue religious study in a setting that excludes women from that opportunity. The disguise gives the plot its premise, while the story also explores the cost of the restrictions Yentl faces.
12. Patrick Swayze as Vida Boheme in To Wong Foo, Thanks for Everything! Julie Newmar
Swayze plays Vida, a drag performer travelling with fellow performers Noxeema Jackson and Chi-Chi Rodriguez. The role is a drag performance within a road comedy; it is not presented as a trans character’s identity.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Trans characters and the casting debate
13. Eddie Redmayne as Lili Elbe in The Danish Girl
Redmayne portrays Lili Elbe, a trans woman, in a story based on her life. Lili’s identity is not a disguise. The film depicts her gender self-discovery and transition, and its casting has been debated because a trans woman was not cast in the lead. PBS SoCal’s filmmaker interview says trans women advised the production and trans performers appeared in small roles; director Tom Hooper also described the film as a reminder of how men have historically prescribed women’s gender roles. That is Hooper’s interpretation of the film’s themes, not a neutral historical finding. PBS SoCal filmmaker interview.
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In 2021, Redmayne said, “No, I wouldn’t take it on now,” and called making the film “a mistake,” while explaining that he had acted with the best intentions. CBS News. In a 2023 interview with The Guardian, he said he believes the part should have gone to a trans performer. He also discussed the tension between actors’ desire to play any role and communities that have historically lacked representation, saying there are parts he would not play “until there’s a levelling.” Those are Redmayne’s views, not a universal rule for casting. The Guardian interview.
14. Hilary Swank as Brandon Teena in Boys Don’t Cry
Swank portrays Brandon Teena, a trans man. This is not a disguise role: Brandon is a man, and the film’s story concerns his life and the violence he faced. The role belongs in a different category from characters who temporarily adopt another gender presentation to fool others.
How to compare these performances
Costume, voice and movement can be part of a performance, but they do not tell the whole story. A useful comparison asks what gender presentation does in each film: create a comic misunderstanding, enable access to an opportunity, shape a stage persona, or express a character’s identity. The films also come from different eras and treat gender differently, so a performance can be technically memorable while its framing or casting prompts questions today.
That is why “nailed” works best as an editorial judgment about a role’s performance and dramatic effect, not a claim that all 15 portrayals are equivalent or beyond criticism.
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