Salt, 2010

Jolie played the role of CIA officer Evelyn Salt, suspected of working for Russian intelligence. According to the plot, the female officer has to transform into a man. Angelina Jolie had to spend several hours in the dressing room to achieve such a plausible transformation.

In this dramatic film by a classic of Spanish cinema, Pedro Almodóvar, Gael García Bernal plays a transvestite. Work on the female image became a new experience in Bernal’s career.

The Danish Girl, 2015

The drama takes place in the 1920s and tells the story of the artist Einar Wegener, who posed for his wife as a woman. Eventually, Einar realizes he no longer wants to be a man and decides to undergo the world’s first sex-change operation. Eddie Redmayne was great in both roles, and the movie about the world’s first transgender turned out to be strong, philosophical, and lyrical.

Breakfast on Pluto, 2005

Breakfast on Pluto is one of the most iconic and complex works in the career of Cillian Murphy. The actor’s character goes from an androgynous teenager to a glamorous blonde.

Jack & Jill, 2011

In the comedy Jack and Jill, Adam Sandler played an employee of an advertising agency (Jack) as well as his crazy sister (Jill). Jill comes to visit Jack and turns his life upside down. For the role in this movie, the actor received two Golden Raspberry Awards — for the worst male and female roles.

3 Generations, 2015

Elle Fanning played a teenager determined to change sex. Those closest to the girl (Naomi Watts and Susan Sarandon) cannot accept that she has decided to become a boy.

Boys Don’t Cry is a dramatic film based on real events. Hilary Swank’s character was born a woman but felt like a man from an early age. In order to get used to the role, the actress cut her hair, worked on her body to make it look more like a man’s, and even lived in the image of a man for a month. Swank received an Oscar for this role.

Mrs. Doubtfire, 1993

Mrs. Doubtfire is known and loved by many of us. And the image of an elderly Mrs. Doubtfire, used by Williams’s character to be hired as a nanny by his ex-wife to see his children every day, cannot but bring a smile.

Hairspray, 2007

In Hairspray, John Travolta plays the role of Edna Turnblad, who works as a laundry lady and hasn’t left her house for 10 years, being shy about her extra weight. It was rather unexpected to see Travolta, usually associated with brutal characters, in such a role.

She’s the Man, 2006

This comedy is a free adaptation of the play Twelfth Night, and it tells how difficult it is to be two people at the same time. Amanda played Viola and her twin brother Sebastian. Amanda’s character wants to teach her ex-boyfriend a lesson and prove that soccer is not only a man’s game.

To Wong Foo Thanks for Everything, Julie Newmar, 1995

Patrick Swayze received the Golden Globe for Best Actor in To Wong Foo Thanks for Everything, Julie Newmar. In this comedy, he played the drag queen Miss Vida Boheme.

Some Like it Hot, 1959

This famous movie doesn’t need a description of the plot. Everyone loved the adventures of two loser musicians forced to pretend to be women, and Jack Lemmon received an Oscar nomination for his role in this film.

Tootsie, 1982

The story of a talented actor who decided to play a female role, turning himself into a woman with the help of clothes and makeup, is another favorite film of many generations. Dustin Hoffman was nominated for an Oscar for Best Actor.