Yentl

Barbra Streisand directed, co-wrote, co-produced, and starred in this 1983 film about a Jewish girl in Poland who becomes a Wholesome Crossdresser so she can receive an education. The movie is set in the early 20th Century and was partially filmed in Prague. As the lead character, Streisand got to belt out several memorable songs.

Yentl secretly is instructed in Talmudic Law by her father, a path that is disallowed to women of the time. When her father dies, Yentl makes the decision to cut her hair, take the name of her dead brother Anshel and disguise herself as a boy so she can enter a yeshiva (Jewish religious school). There she becomes friends with her roommate Avigdor, who is engaged to marry a sweet, gentle, and beautiful woman named Hadass.

Complications arise: One day while many of the men are gone swimming, Yentl realizes she is falling hard for Avigdor and can't act on it without blowing her cover. Then suddenly, Hadass's family breaks off Avigdor's engagement. Avigdor had lied about his brother dying of consumption where in truth his brother had gone insane and committed suicide, and the family feared the sickness might run in the family. Distraught, Avigdor comes up with what he thinks is an excellent idea - as his best friend, Anshel should take his place as the groom, and as a result he won't be cut off from Hadass completely. Yentl balks, but she doesn't want to lose Avigdor (who almost leaves the town in disgrace) and Hadass is a nice enough woman. In the ensuing scenes filled with her terror and a few close calls, she ultimately goes through with the marriage.

Since Hadass is nervous about the arrangement, still attached to Avigdor and and in no more hurry to consummate the marriage than Yentl is, things settle down for a bit. However, when the three of them are together, Yentl watches Avigdor staring longingly at Hadass and starts to realize that he's too deeply attached to her to ever reciprocate what Yentl feels for him. Meanwhile, inspired by Yentl's wit and brains, the innocent Hadass starts to express an interest in academic study, which Yentl, recognizing the thirst, is all too glad to indulge. What she didn't intend was for Hadass to start to love her because of it, and when Hadass starts to come on to her, Yentl realizes she can't keep up the charade. She reveals the truth to Avigdor, who is initially furious, then accepting, and even admits he was hiding some feelings for her too. Avigdor and Hadass get back together and Yentl leaves for America where she might have a chance at perusing her opportunities more openly.

The script was based on a 1968 play written by Leah Napolin which was itself based on a short story from the early 1960s by Isaac Bashevis Singer. Singer ultimately panned the movie production, but it became a box office hit. The movie won an Academy Award for Best Original Score; the movie won a Best Picture Golden Globe in the musical/comedy category and Barbra Streisand became the first woman to win a Best Director Golden Globe Award for the film. Amy Irving, who played Hadass, has the rare distinction of being nominated for both the Best Supporting Actress Oscar as well as the Golden Raspberry Award for Worst Supporting Actress - only the latter of which she "won". (The Razzies also nominated Barbra for Worst Actor and the movie for Worst Score, which is either a sign that they're meant to be tongue in cheek or a sign that some people are deeply divided about its merits.)

This film contains examples of:
"He loves her, she loves him, he likes me, I like her, and I've reason to think she likes me.
 * All Love Is Unrequited: Both Yentil for Avigdor and Avigdor for Hadass (though she loves him, they're prevented from consumating it).
 * Chick Flick: of the drama variety
 * Dawson Casting: Barbra Streisand was 40 at the time of filming. In the original short story by I.B. Singer, Yentl seems to be younger than 20, although Streisand made the character 28 years old in the movie. Interesting in that the plot revolves around the main character disguising herself as a boy to study in a yeshiva, which when done by a 40-year-old woman stretches the imagination a bit. Then again, so does Streisand's Brooklyn accent in a movie set in Poland around the turn of the century. Well, Streisand does have some difficult singing to do; you couldn't really expect her to do it in a Polish accent.
 * Different for Girls
 * I Am Becoming Song: "No Matter What Happens", "A Piece of Sky"
 * I Want My Beloved to Be Happy: Avigdor for Hadass when his engagement to her is broken off by her parents and proposes that Yentl marry her. Yentl for Avigdor when she decides to reveal herself and leave Hadass to him while she leaves for America.
 * I Want Song: "Where is it Written?"
 * Incredibly Long Note: Barbra Streisand's final number (Papa Can You Hear Me/A Piece of Sky); her last note clocks in at over 20 seconds. Babs in general is famous for these.
 * The Ingenue: Hadass
 * Ironic Echo: There are two: "Nothing's impossible!", first uttered to the titular character by her study partner Avigdor after he asks her/him to marry his ex-fiancee, later uttered by her when Avigdor almost leaves town after she refuses the favor. The other is "God will understand. I'm not so sure about the neighbors," first said by Yentl's father when asked why he is closing the windows if God will understand that his teaching her Talmudic law, which was forbidden to women at the time, is not with ill intent. It is said again by her to Avigdor's ex-fiancee (now her legal wife) in the same context.
 * Love Triangle: A slightly unconventional one. As Yentl puts it:

She keeps him, he keeps her, I keep things as they were, it's a perfect arrangement for three!"

""I didn't want to touch you. I didn't know why. I thought there was something wrong with me. I loved you... ""
 * It gets more complicated later when Hadass starts to fall in love with Yentl/Anshel.
 * Sweet On Polly Oliver: After the heroine reveals her, ahem, "self" to her love interest, he bitches her out for a while, and then reveals the following to her:


 * Justified. Yentl's disguise is pretty crappy (much worse than the equivalent in Tootsie or Mrs. Doubtfire for example.) The miracle is that anyone thought she was a man, not that a straight man was attracted to her. It more makes you wonder about Avigdor's fiancee.
 * Sweet Polly Oliver: The main character became a man in order to attend a school in Jewish Talmudic Law, which was forbidden for women at the time. It made for some really weird love triangles.
 * Twelfth Night Adventure: The film was set during a time when women were not to become educated.