Cross-Dressing in the Movies Trivia Quiz

Answer: Harvey Fierstein

Harvey Fierstein, an actor and a playwright, was born in 1952 in Brooklyn, New York, USA. He wrote the book for "La Cage aux Folles" (1983) which won him a Tony Award for Best Book of a musical.

Uncle Frank Hillard was played by Harvey Fierstein. Frank Hillard was Daniel's older brother and through his skills as a make up artist, he turned Daniel into Mrs. Doubtfire. Daniel (Robin Williams) and Miranda (Sally Field) had a bitter divorce, in which Miranda thought it would be best to stop Daniel from seeing the three children. With the help of both Frank and Jack, Daniel was transformed into Mrs. Euphegenia Doubtfire and was hired by Miranda to be a nanny to the three children. Daniel pulled off the masquerade with expertise because he was an expert at dubbing voices, so Miranda was unable to tell that Mrs. Doubtfire was actually Daniel. Over time, the children discovered the truth about Mrs. Doubtfire and so did Miranda, when they were all out to dinner along with Miranda's new boyfriend Stu Dunmeyer (Pierce Brosnan). Finally, Daniel was able to get a job dressed as Mrs. Doubtfire in a children's show. When this was discovered by Miranda, she went to Daniel and patched things up so he could be with the children again.

Matthew Lawrence played the role of Chris Hillard, Daniel's and Miranda's son.
Martin Mull played the role of Miranda's business partner.
Scott Capurro played the role of "Aunt" Jack Hillard, who was Frank's partner and aided Frank in the task of turning Daniel into Mrs. Doubtfire.

Answer: To enter religious training

Barbara Streisand played the role of Yentl Mendel, who was the only child of widower Rebbe Mendel, a teacher of Talmud (Jewish Law) to local boys. Girls were not permitted to learn those laws, at that time. When Rebbe died, Yentl was left all alone so she decided to disguise herself as a boy and take on the name of her deceased brother Anshel.

She managed to get admitted to a Yeshiva (Jewish educational institution), where she could study the Torah (Pentateuch, or Five Books of Moses) and the Talmud (central text of mainstream Judaism, such as laws, ethics, philosophy, etc. of the Jewish peoples), as well as other teachings that girls were not permitted to learn. Eventually Yentl (Anshel) made friends with Avigdor. Since Avigdor had a brother who committed suicide, his fiancee, Haddas's, family called off their wedding, which resulted in "Anshel" being asked to stand in as a substitute and become Haddas's husband. Of course the marriage was never consummated and over time Yentl revealed that she was a she and not a he. Through it all, Avigdor and Haddas eventually ended up back together and Yentl went to America to seriously study in Yeshiva, as a woman.

Answer: Dorothy Michaels

As an unemployed actor named Michael Dorsey, Dustin Hoffman donned the disguise of Dorothy Michaels, which landed him a role in a soap opera called "Southwest General" in the film "Tootsie". Through his time period as Dorothy, he became lost in the role and intrigued women all over the city.

His role as Dorothy inspired the women to break free from the controlling influences of men and to become more like the soap star played by the impersonator, Dorothy Michaels. Eventually Dustin Hoffman's role as Dorothy Michaels got him into some comical problems, because he fell in love with his female co-star, Julie Nichols (Jessica Lange), but the co-star's father, Leslie Nichols (Charles Durning), was in love with "Dorothy".

A male co-star in the soap opera, John Van Horn (George Gaynes), also wanted Dorothy's affections bestowed upon him. Eventually the guise was revealed. Julie was furious but in time, she forgave Michael, admitting that she missed Dorothy and asked, jokingly, if she could borrow some of Dorothy's clothes.

Answer: Just One of the Guys (1985)

Believing that sexism would be the main reason that she would be passed by for a summer internship at the local newspaper, Terry Griffith (Joyce Hyser) became determined to win that internship. She went undercover, as a boy at another high school. She resubmitted her article, in the guise of a boy and continued with her masculine disguise.

At the new high school she found herself having to ward off some bullies as well as a persistent female admirer. She met Rick (Clayton Rohner) and discovered that she liked him a lot.

When the senior prom took place, Terry's boyfriend Kevin (Leigh McCloskey) showed up, which forced Terry to reveal that she was not a he, but was indeed a she. Rick was furious with her and rejected Terry. Humiliated and with a broken heart, Terry wrote an article about the exploits, trials and tribulations of being a girl impersonating a boy.

She returned to her own school and her article was printed in the newspaper earning her the internship. When Rick, who was really angry with Terry, read the article he reconciled with Terry.

Answer: Sylvia Scarlett (1935)

In the 1935 film "Sylvia Scarlett", Henry Scarlett (Edmund Gwenn) had to escape from France and go to England because of embezzlement charges. In order to prevent being detected Henry had his daughter Sylvia (Katherine Hepburn) disguise herself as Henry's son with the name Sylvester. Conman Jimmy Monkley (Cary Grant) joined Henry and Sylvester and they ventured into a short career of crime.

When they ended up going on the road with a traveling caravan show, Sylvia/Sylvester fell in love with Michael Fane (Brian Aherne), a handsome artist and decided to abandon her disguise.

Answer: Got shot and killed

Brandon Teena was a transgendered teenager who much preferred a male identity instead of a female identity. As Brandon, Hilary Swank's character was one of they guys in a tiny town in Nebraska. As a male, charming the girls was easy and life was going really well. Nobody knew that Brandon Teena was really a girl. Brandon's best friend Candace (Alicia Goranson) discovered that Brandon Teena was really Teena Brandon, went to a bar and revealed the news to John Lotter (Peter Sarsgaard) and Tom Nissen (Brendan Sexton III).

Although Lotter and Nissen chased Brandon/Teena and raped her, she escaped and eventually filed a rape report. Nissen and Lotter became enraged, set out and found Brandon hiding at Candace's farm house. Sadly, Nissen and Lotter shot and killed Brandon/Teena and Candace.

Answer: Robin Williams

"The Birdcage" (1996) starred Robin Williams as Armand Goldman, owner of a drag club called The Birdcage. Dan Futterman played Val Goldman, Armand's son from a brief affair many years ago. Nathan Lane played Armand's drag queen companion Albert Goldman.
Val came home one day and announced that he was getting married and was engaged to Barbara Keely (Calista Flockhart). She was the daughter of Senator Kevin Keely (Gene Hackman). Armand and Albert decided to take on a more serious role to make things appear as straight laced as possible, for the benefit of Val. Val's birthmother, Katherine, agreed to masquerade as Val's mother in order to make things appear normal when meeting the Keelys, but she got caught in traffic. Albert had no choice but to dress up as a woman and take on the role of Val's mother. The Keelys believed the charade until Katherine arrived and eventually the Keelys were dressed up in drag to be able to avoid the press. Despite all of the mix up and masquerade mess ups, Val and Barbara got married with everyone present.
Robin Williams is an American actor known for his role as Mork in the television series "Mork and Mindy" (1978-1982). Some of the movies starring Williams include "Good Morning, Vietnam" (1987), "Awakenings" (1990) and "Dead Poets Society" (1989).

Answer: Jack Lemmon and Tony Curtis

Jerry/Geraldine (Jack Lemmon) and Joe/Josephine (Tony Curtis) were a pair of musicians who were struggling. They witnessed a murderous crime and had to run for their lives. They got out of town. Dressed as women, they got jobs in an all-girl band. The vocalist was Sugar Kane (Marilyn Monroe) and both men were smitten with her. Eventually the gangsters ended up at the same hotel where the band was performing.

They saw Joe and Jerry and many chases ensued. Sugar fell in love with Joe while Jerry had to reveal to Osgood Fielding III (Joe E. Brown) that he was a man and could not marry Osgood, who had proposed earlier. Jack Lemmon starred in over sixty films and is well known for his role as Felix Unger in "The Odd Couple" (1968) and for his part in "Grumpy Old Men" (1993). Tony Curtis acted for sixty years and was known for his roles in "Houdini" (1953) and as Albert DeSalvo in the 1968 film "The Boston Strangler".

Answer: Nuns on the Run (1990)

Brian Hope/Sister Euphemia (Eric Idle) and Charlie McManus/Sister Inviolata (Robbie Coltrane) were part of a gang but when their boss found out that they wanted to quit, they were marked to be killed during a robbery. Brian and Charlie decided to go through with the robbery but fled with the goods. Since their getaway didn't quite work out as expected the boys decided to hide out as nuns in a teacher training school.

The gang boss Casey (Robert Patterson) put a bounty on the heads of Brian and Charlie. Eventually they had to reveal to the nuns what had happened to them.

While booking a flight to Brazil along with Faith (Camille Coduri), who loved Brian, a security guard asked to speak to anyone called Hope or McManus. That request quickly persuaded the duo to disguise themselves as flight attendants and make their escape.

Answer: Just Like a Woman (1992)

Adrian Pasdar played the role of a yuppie transvestite in his thirties. When his wife arrived home unexpectedly early, she discovered female clothing spread around their apartment. She misunderstood what was going on and threw Gerald out, along with all of the female attire. Gerald rented a room at Monica's (Julie Walters) house where, over time, they became friends and then lovers. Monica learned about Gerald's alter ego, Geraldine, and she both accepted and supported Gerald.

When Gerald got arrested, while wearing a dress, Monica went to his rescue and helped him to regain his self-respect.