AUDITIONS

Be a part of an all-star cast and crew

Into the Woods Auditions: Saturday October 31 from 1:00-6:00PM; Sunday November 1 from 7:00PM-10:00PM; Youth Auditions on Sunday November 1 from 10:00AM-1:00PM

About the Show.
INTO THE WOODS
Music and Lyrics by STEPHEN SONDHEIM
Book by JAMES LAPINE
Originally Directed on Broadway by James Lapine
Orchestrations by Jonathan Tunick

One of Sondheim’s most popular works, Into the Woods is a musically sophisticated show with the opportunity to feature actors adept at dark comedy. The characters of Into the Woods begin as recognizable fairy-tale archetypes, but the musical gradually exposes the complicated human beings underneath as each face the consequences of getting their wish. Each enters the woods believing that fulfillment lies in obtaining a particular wish; what emerges is a more adult understanding of desire, responsibility, loss, parenthood, intimacy and transformation.

Director. Bryce Chaddick

Musical Director. Jenny Shiroma

About Auditions.
Please prepare a 32-bar cut of a contemporary musical theatre song that shows off your vocal range and acting skills. Relax and show us your personality – give us a glimpse of who you are as a human being. You may also have a second, contrasting song ready to sing as a backup during the audition, if requested. Please bring sheet music in your proper key (no onsite transpositions). An accompanist will be provided. No recorded music, or a cappella, please.

You may also prepare one of the cuts from the show – Click here to view the music for auditions

FOR YOUTH CALL*** We are looking for auditioners who are under 5 feet tall and can present as an 8-12 year old. If you do not meet these requirements, but are under 18 please submit an audition application for ADULT AUDITIONS. 

Those auditioning for the Children’s Ensemble during the YOUTH AUDITION session should prepare the ITW YOUTH AUDITION MUSIC CUT provided by Diamondhead located here. As identified on the music cut, Girls are asked to prepare GROUP 1, Boys are asked to prepare GROUP 2. All youth will be scheduled in groups for a 30 minute session. In the session you will be asked to sing the asked material and participate in a group activity (no preparation needed for that portion).

What to Bring. Please have a complete list of any conflicts or possible conflicts you may have with rehearsals and performances between November 3, 2026– February 14, 2027 . If you are cast in INTO THE WOODS, no additional conflicts, except those presented at your audition, will be accepted. Headshots and resumes preferred, but not required.

Audition Dates.
Saturday October 31, 1:00-6:00PM (ADULT AUDITIONS) on the Diamondhead Theatre Mainstage
Sunday November 1, 10:00AM-1:00PM (YOUTH AUDITIONS) in the Diamondhead Theatre Rehearsal Hall
Sunday November 1, 7:00PM-10:00PM (ADULT AUDITIONS) in the Diamondhead Theatre Rehearsal Hall

If you are out of town/unavailable for auditions and callbacks but available for the production, you may submit a tape by submitting an audition submission form and selecting ‘Virtual Submission.’ You will be contacted regarding specifics of virtual audition requirements. All virtual auditions will be due by October 31. Please contact productions@diamondheadtheatre.org with further questions.

Audition Sign Up. Auditions by appointment are preferred. “Drop ins” are permitted as time allows, but please do not expect to be seen immediately. Auditions will be held in the following locations:

Saturday October 31, 1:00-6:00PM – ADULT AUDITIONS – Diamondhead Theatre Mainstage (stage door entrance at top of staircase from rear parking lot)
Sunday, November 1, 10:00 AM – 1:00 PM – YOUTH AUDITIONS – Diamondhead Theatre Rehearsal Hall  (see casting breakdown for Children’s Ensemble)
Sunday November 1, 7:00-10:00PM- ADULT AUDITIONS – Diamondhead Theatre Rehearsal Hall (rear parking lot/costume shop entrance)

Click here to sign up to audition.

Callbacks.
Monday November 2, 7:30-10PM
Callbacks are on Monday, November 2 (by invitation only). Not being called back in no way infers final casting decisions. At callbacks, you may be asked to read scenes from the show or learn and sing songs from the show.

Rehearsal Dates. Rehearsals officially begin on Tuesday November 3. However, the rehearsal schedule will vary based on availability at the beginning of the process. Rehearsals are normally 6 days a week with alternating days off. Rehearsal times are Mondays – 7:30 – 10pm; Tuesday-Fridays 7:00-10:00pm; Saturdays 10:00-2:00pm; Sundays 2:00-5:00pm or 6:00-9:00pm. Please view the tentative rehearsal schedule for dates. There will be no rehearsal on Thursday November 26, Thursday December 24-Friday January 1.

Into the Woods Calendar

2026 Show Dates. January 21-February 14

CHARACTER BREAKDOWN

ALL ROLES ARE OPEN. We are committed to non-traditional casting, so all appropriate ages, body types, colors, ethnicities, disabilities and gender identities are encouraged to audition. Each cast member will also pledge to uphold our anti-bullying and anti-harassment policies before beginning rehearsals. We are dedicated to an open and inclusive create environment that fosters artistic and personal growth.

For THIS production of Into the Woods will be seeking strong actors (who sing) to portray the following characters.  While all characters are archetypes and there are many comedic moments, all should possess genuine emotional stakes and avoid caricatures – even the cruel or selfish characters should have an internally coherent understanding of themselves.   

Please note THIS production will also cast a CHILDREN ENSEMBLE (details below).

 

Commanding, intelligent, charming, articulate, and reassuring, the Narrator occupies the psychologically comfortable position of the observer: he understands life by narrating it rather than fully participating in it. As the story grows darker, however, his certainty becomes increasingly fragile, and not nearly as detached or secure as he pretends to be.

The Mysterious Man, by contrast, is messy, evasive, guilty, and personal. The Narrator can describe abandonment, fear, desire, and consequence from a safe intellectual distance. The Mysterious Man has actually lived through those failures.

Vocal Range: G2–E4

Brilliant, formidable, emotionally wounded, funny, possessive, and capable of both tremendous love and tremendous cruelty, the Witch sees dangers and hypocrisies that others would rather ignore. Her relationship with Rapunzel is rooted in genuine devotion distorted by fear: having experienced betrayal and loss, she attempts to eliminate uncertainty through control, preferring Rapunzel safe and resentful to independent and vulnerable. Her tragedy lies in confusing protection with possession and being needed with being loved, forcing her to confront the painful truth that loving someone deeply does not grant the power to keep them from leaving.

Vocal Range: F3–G5

A decent, loving, anxious man whose insecurity has convinced him that responsibility means handling everything himself, the Baker is far more comfortable solving practical problems than exposing emotional vulnerability. His inherited family shame makes him suspicious of dependence and fearful that he may repeat the failures of the father who abandoned him. Though deeply devoted to his Wife, he can become controlling or withdrawn when overwhelmed.

Vocal Range: Ab2–G4

Warm, capable, intelligent, pragmatic, and emotionally curious, the Baker’s Wife genuinely loves her marriage while also sensing that parts of herself remain unexplored. Her desire to become a mother begins the journey, but the woods awaken ambition, sensuality, independence, and a fascination with lives she might have lived. More psychologically flexible than her husband, she adapts quickly and often rationalizes choices when desire becomes compelling, ultimately confronting the mature truth that a person can be grateful for the life they have while still mourning or longing for possibilities they did not choose.

Vocal Range: F3–G5

Thoughtful, sensitive, perceptive, and far more complex than the passive fairy-tale heroine she first appears to be, Cinderella has learned to survive neglect and humiliation through patience, fantasy, and accommodation rather than confrontation. She deeply desires another life but struggles to trust her own wishes enough to act on them, often becoming immobilized by her ability to see competing truths. Her journey is ultimately about developing agency: learning that maturity does not mean finding the perfect choice, but accepting responsibility for the choices she makes.

Vocal Range: G3–G5

Open-hearted, impulsive, imaginative, and standing awkwardly between childhood and adulthood, Jack experiences the world with enormous emotional immediacy and wonder but has not yet developed a mature understanding of consequence. His adventures give him a sense of competence, identity, and emerging masculinity, yet his actions often outpace his moral comprehension. His coming-of-age lies in discovering that courage alone does not make someone an adult; adulthood also requires accountability for the effects one’s choices have on others. Note: In this production, JACK will be cast as an adult playing younger.

Vocal Range: B2–G4

Bright, assertive, impulsive, funny, and convinced she understands far more about the world than she actually does, Little Red begins with the confidence of a child who has not yet encountered enough danger to understand vulnerability. Her encounter with the Wolf violently disrupts that innocence, and she responds by adopting suspicion and toughness as forms of self-protection. Her apparent fearlessness after the experience is therefore both genuine resilience and psychological armor, marking one of the show’s clearest transformations from childhood certainty into a more complicated awareness of danger and consequence. Note: In this production, LITTLE RED will be cast as an adult playing younger.

Vocal Range: Bb3–F5

Sensitive, romantic, emotionally intense, and profoundly sheltered, Rapunzel has been loved but never allowed to fully become a separate person. The Witch’s overprotection has deprived her of opportunities to develop autonomy, emotional regulation, and an identity independent of her mother, making her yearning for the outside world an urgent need for individuation rather than merely romantic longing. When freedom finally arrives, the reality of the world overwhelms the fantasy she created around it, and her emotional volatility reflects isolation and arrested development rather than simple foolishness.

Vocal Range: B3–A5

Privileged, competitive, emotionally immature, and deeply dependent on external validation, Florinda and Lucinda have absorbed their mother’s belief that attention, beauty, and status are scarce resources. Cinderella’s natural grace threatens them because they have learned to measure themselves comparatively, making another person’s success feel like evidence of their own inadequacy. Beneath their vanity and cruelty lies insecurity, dependence on maternal approval, and a desperate need to be chosen, while their sisterly relationship shifts constantly between alliance and competition. Note: Actors chosen for these roles may also understudy other roles.

Vocal Range: C4–Ab5

A cow.

But this part requires an actor more than a comic puppeteer or mime; he / she is Jack’s first attachment object, his companion, and one of the clearest embodiments of innocence in the musical and should be treated with emotional seriousness, because her presence quietly asks whether something must be useful, productive, or valuable in order to deserve love.

NOTE: The following roles may be cast with a single actor or may be split into separate roles and may understudy other roles:

Jack’s Mother – Vocal Range: Bb3–Gb5
Exhausted, practical, fierce, and shaped by years of scarcity and responsibility, Jack’s Mother has lived so long in survival mode that her love frequently emerges as criticism, frustration, and control. She sees danger where Jack sees possibility because she has spent years anticipating consequences he cannot yet imagine. Beneath her impatience is profound fear for her son’s safety and future, making her struggle a painful parental paradox: to shield him from the world or to allow him his own journey.

Cinderella’s Stepmother – Vocal Range: A3–F#5
Socially ambitious, emotionally hard, and determined to secure advantage for herself and her daughters, Cinderella’s Stepmother views the world as fundamentally competitive and believes status, desirability, and security must be fought for. Cinderella threatens her because she possesses qualities—beauty, grace, youth, authenticity—that cannot easily be controlled or manufactured, and rather than nurture what she fears, the Stepmother attempts to diminish it. Her cruelty is therefore not arbitrary but rooted in insecurity, social calculation, and a worldview in which affection is conditional and worth is measured through victory over rivals.

NOTE: The following roles may be cast with a single actor or may be split into separate roles and may understudy other roles:

THE WOLF – Vocal Range: Bb2–Gb4
Charismatic, predatory, and driven entirely by appetite, the Wolf understands desire without conscience and instinctively recognizes how to make danger feel enticing. Psychologically, he represents appetite unconstrained by empathy—the impulse to consume simply because something is desirable—and is most unsettling when played with genuine charm rather than obvious menace.

CINDERELLA’S PRINCE – Vocal Range: B2–F4
Magnetic, entitled, romantic, and fundamentally addicted to pursuit, Cinderella’s Prince has been raised to believe that wanting something and deserving it are nearly synonymous. He excels at courtship because pursuit allows him to experience himself as passionate, heroic, irresistible, and transformed by longing, but he struggles when fantasy becomes ordinary life.

NOTE: The following roles may be cast with a single actor or may be split into separate roles and may understudy other roles:

CINDERELLA’S MOTHER – Vocal Range: E4–F4
A maternal presence existing somewhere between spirit, memory, and Cinderella’s internalized sense of unconditional love, she represents emotional safety, ancestry, intuition, and a connection to a time before Cinderella learned that affection had to be earned through obedience.

GIANT’S WIFE
Immense, grieving, relentless, and far more emotionally comprehensible than the characters initially allow her to be, she enters the story as an apparent monster but is fundamentally a bereaved spouse demanding accountability for a violent loss. Her scale makes her frightening, yet her psychology is recognizably human: grief has narrowed into rage, and rage into a need to identify someone who can be made responsible.

GRANNY
Warm, vulnerable, practical, and emblematic of the older generation, Granny represents the ordinary human fragility that fairy tales often treat casually. Unlike the more symbolic maternal figures in the story, she is grounded in domesticity and dependence, making the violence done to her feel intimate rather than abstract.

NOTE: The following roles may be cast with a single actor or may be split into separate roles and may understudy other roles:

RAPUNZEL’S PRINCE
Vocal Range: C#3–E4
Romantic, privileged, competitive, theatrical, and deeply invested in experiencing himself as a heroic lover, Rapunzel’s Prince is drawn to obstacles because they intensify both his desire and his sense of importance. Like his brother, he has learned to equate yearning with love, but his romantic suffering is amplified by sibling competition, with each Prince treating passion almost as proof of personal greatness.

THE STEWARD
Controlled, dutiful, pragmatic, and morally evasive, the Steward is a man who has spent his life serving systems of authority and has learned to confuse obedience with virtue. When confronted with a crisis, he makes a brutal decision and rationalizes it as a necessity, revealing how easily responsibility can disappear behind hierarchy, protocol, and fear.

3 Males + 3 Females.
These are non-speaking roles, but who will sing and act. Seeking expressive, mature, but younger looking actors who can present as 8 to 12 years of age and are preferably under 5 feet tall. Note: Please register for Sunday morning auditions only.

1 Male | 1 Female

INTO THE WOODS is presented through special arrangement with Music Theatre International (MTI).
All authorized performance materials are also supplied by MTI.
www.mtishows.com

Cast of volunteers

Oahu’s abundance of talented performers light up our stage show after show. Diamond Head Theatre’s productions also feature guest artists and Broadway performers.