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Cinderella
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Cinderella is at once beautiful, in a yet-to-be-discovered sort of way, and surprisingly clumsy and awkward. She persistently pursues her wish to go to the King's Festival, yet finds that "the Festival" ultimately does not meet her expectations. She should be able to sing well and be funny.
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Jack
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Jack's own mother expresses her fear that Jack may not be the brightest boy. The fact that Jack's best friend is the family cow, Milky White, further brings into question his intelligence. However, Jack may enter the woods as a simple boy, but he leaves much more grown-up. You'll want to cast an actor capable of this transition. In addition to having many lines, Jack is responsible for singing two of the best-loved songs, "I Guess This is Goodbye" and "Giants in the Sky." Therefore, he should be an excellent singer and a good actor. Further, it helps to have a young man whose voice has not yet changed, although the score allows for a changed voice. This is a role that could conceivably be played by a young woman without changing the intended gender of the character. Good actor, excellent singer, capable of transitioning from a simple boy to a more grown-up young man
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Jack's Mother
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This woman is overworked, a bit frazzled, and overwhelmed with the tasks of raising a young boy, running a farm, and making ends meet. Jack's Mother is described physically as "not quite pretty" and should be comfortable playing frumpy. This is mainly an acting role and therefore requires an actress with an easily projected, authoritative voice. Good actress, strong speaking voice
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Baker
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The Baker changes the most as a result of his journey through the woods. At first he is reluctant to seek the help of his wife. It is through the tribulations of gathering the Witch's items that the Baker realizes, in order to achieve his wish, it will take the help of his wife. The Baker has one of the most difficult roles. He must be strong willed, yet the audience must like him; while he's denying the help of his wife, he must also portray a sense of needing and even wanting her help. The audience should never doubt the Baker is a good-hearted person, trying to do what is right. Strong actor, good singer
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Baker's Wife
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Into the Woods is truly an ensemble show. However, it is the Baker's Wife who drives the show forward and ties the characters together. The Baker's Wife is strong, determined, and patient. The audience should identify with her and root for a successful fulfillment of her wish. The role requires excellent singing and acting, plus a good sense of comic timing. Excellent singer and actress, comic timing, determined and patient, drives the play forward
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Little Red Ridinghood
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Pushy, bratty, over-fed, and spoiled best describe this character at the opening of the show. Her journey teaches her some very important lessons regarding strangers and trust. Little Red must be able to be loud vocally (think ANNIE gone very bad) and an actress able to be all the above, and still draw the audience's sympathy. Good actress, strong voice, pushy, bratty and spoiled
Witch
The Witch begins the show as ugly, old, extremely aggressive, sarcastic, and powerful. Ultimately, she sacrifices her power for beauty. The Witch should be mysterious and mischievous, and yet we learn that she is really only doing what she thought was best for her child. The Witch is perhaps the ultimate "character" role and should be played by an actress able to physically and vocally interpret the role. Good actress, strong singer, mysterious, mischievous, mother to Rapunzel
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Cinderella's Mother
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This role is a one scene wonder. The voice should be pleasant. Cinderella's Mother is a collection of remembered mannerisms and sayings
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Mysterious Man
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This role is all that the name implies. The role may be doubled by the Narrator, as on Broadway, or may be played by a different actor.
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Narrator
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This is the character who describes the action, but eventually gets involved...may be played by a woman- Engaging, charismatic, strong speaking voice, some singing, may double as Mysterious Man.
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Wolf
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The Wolf can be played any number of ways. However, he should be properly slimy and a bit creepy. This role may be doubled by one of the Princes.
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GRANNY Good speaking voice, fiesty and fierce, may be doubled with Cinderella's Mother
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Rapunzel
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Rapunzel must stand up to her mother and eventually leave her for the world. The role requires an excellent high soprano voice.
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Steward
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This servant to Cinderella's Prince is a nice featured role. Featured role, good singer
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Cinderella’s Family
the stepmother Good actress, good singer, selfish, mean and nasty
lucinda
> Good actresses and singers, stepsisters to Cinderella-spoiled brats florinda
Cinderella’s father Some group singing, seemingly no interest in his daughter's well-being, in one scene
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Rapunzel's Prince and cinderella's prince
Pompous, conceited, and self-absorbed are the best ways to describe these brothers. They should be able to carry themselves with confidence that defies the Richter scale. They also have a bit of sibling rivalry! Both should be good, solid singers.
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