ANNIE AND DIARY OF A WIMPY KID! - Woodstock Arts Non Equity Auditions

Diary of A Wimpy Kid

Creative Team -

Naoki Breger, Director - Music Director and Choreographer TBD

Annie

Creative Team

Brian Wittenberg, Director - Lucas Tarrant, Music Director - Alex Self, Choreographer

Age Range

10+, 8+ can submit virtually.

General Auditions

March 15th and 16th

Callbacks - Diary of A Wimpy Kid

March 21st

Callbacks - Annie

March 22nd

What To Prepare

Please prepare one minute of any song in the style of any show.

Payment

Actors 18 and up will be paid a stipend of $150 at the end of the run of performances

About

Audition form is at the bottom of the page!

DIARY OF A WIMPY KID

Middle school, ugh. It’s the worst. But Greg is determined NOT to be at the bottom of the popularity chart. He’ll leave that to his weird neighbor, Fregley. Or maybe Greg’s best friend, Rowley Jefferson. But it’s not going to be Greg… no way.

Rehearsals/Important Dates –

Rehearsals Start – March 31st Mon/Tues/Thurs from 6:30p-10p
First Saturday – May 30th from 9a-5p
Q2Q – Tues June 2 and Thurs June 4 from 6p-10p
Tech Week – Sat June 5 from 9a-5p Mon June 8&Tues June 9 from 6p-10p

Performances – June 10 – 24, 2026 (
Show Page)

ANNIE

With equal measures of pluck and positivity, little orphan Annie charms everyone’s hearts despite a next-to-nothing start in 1930s New York City. She is determined to find the parents who abandoned her years ago on the doorstep of a New York City Orphanage that is run by the cruel, embittered Miss Hannigan. With the help of the other girls in the Orphanage, Annie escapes to the wondrous world of NYC. In adventure after fun-filled adventure, Annie foils Miss Hannigan’s evil machinations… and even befriends President Franklin Delano Roosevelt! She finds a new home and family in billionaire Oliver Warbucks, his personal secretary, Grace Farrell, and a lovable mutt named Sandy.

Rehearsals/Important Dates –

Rehearsals Start – April 28th Mon/Tues/Thurs from 6:30p-10p
First Saturday – June 27th from 9a-5p
Q2Q – Tues June 30 & Thurs, July 2 from 6p-10p
Tech Week – July 6th – 9th from 6p-10p

Performances – July 10 – 26, 2026 (
Show Page)

Pay Rate –

We are able to pay actors aged 18+ a stipend of $150 for this production, with a $25 bump in pay for understudies/swings when going on for a performance, capped at $200.

PREPARATION

Woodstock Arts is deeply committed to building an inviting and inclusive arts community that celebrates the individual and diversity and treats everyone with fairness and respect. We invite artists of all genders, races, ages, sizes, and sexual orientations, as well as artists with disabilities to participate. We want to represent diverse communities in our organization and welcome you here.

Woodstock Arts is taking measures to ensure your safety and well-being. We want to make this experience as comfortable, safe, and fun as possible for everyone involved.

Auditions will be in-person on March 15th and 16th, from 5p.m (on the 15th) and 6 p.m (on the 16th) until 10 p.m.

Video audition submissions will be accepted until Sunday, March 15th, at 8:00p.m. Auditions received after this time may not be considered. You can send your Video Submission to
zach@woodstockarts.org. Please Slate before your video audition. (NOTE: you will still need to fill out the online audition form along with a video submission.)

In-person callbacks for DIARY OF A WIMPY KID will be on Saturday, March 21st, in the afternoon between 11 a.m and 5 p.m.

In-person callbacks for ANNIE will be on Sunday, March 22nd, in the afternoon between 2p.m and 8 p.m.

Information about callbacks will be emailed separately.

For your audition please prepare-Please prepare a one minute cut of a song that is in the style of either show. Please send your song cutting to Zach (zach@woodstockarts.org), and we will play it for you in the room during your audition.

CASTING BREAKDOWNS- All roles are open ethnicity unless otherwise stated.

DIARY OF A WIMPY KID Character Breakdown

We are able to cast a company of 22 actors (including swings). Most ensemble roles will double in some fashion.

ANNIE Character Breakdown

We are able to cast a company of 14 actors (including swings). Most ensemble roles will double in some fashion.

Even though these characters are derived from a comic strip and fit into several common character archetypes, this production will treat them as true human beings with complex and multifaceted lives. In general, play into the honesty of their lived circumstances rather than into stereotypes or camp.

Annie – Annie is a complex, tough, streetwise urchin who is surprisingly vulnerable when she thinks she might lose what has become most important to her: her newfound “family.” She has a ton of spunk and is the natural leader of the orphans. She is simultaneously motherly towards the orphans and a spitfire ready to go after her hopes and dreams – and encouraging others to do so as well. Female-presenting, Child to play 10-12. Range: G5 – A3

Oliver “Daddy” Warbucks – A successful businessman with a warm heart. Rich, stiff-collared, bullish. He is a captain of industry, but underneath his intense and sometimes prickly exterior, he has a huge heart that cares for the people who work for him and eventually the young girl who comes to live with him. Male-presenting, to play 40-50. Range: Gb5 – B3

Miss Agatha Hannigan – The orphanage matron who hates children but is fond of liquor. Very disillusioned, bitter, and cold. The job at the orphanage is the only one that would take her, and she takes out her anger at her circumstances on the orphans, especially Annie. Female-presenting, to play 30 – 40. Range: F5 – A3

Rooster Hannigan – Miss Hannigan’s brother and a conman constantly looking for the next, best way to get a quick buck. He’s sleazy and slick and will do whatever it takes to get what he wants. Male-presenting, to play 30 – 40. Range: G5 – B3

Lily St. Regis – Rooster’s girlfriend who has joined in his schemes to con people out of money. Beneath her polished confidence lies someone who understands survival all too well, masking hard-earned street smarts with effortless glamour. Female-presenting, to play 20 – 30. Range: G5 – B3

Grace Farrell – The poised, intelligent secretary to Oliver Warbucks, balancing professionalism with genuine warmth and compassion. Elegant and level-headed, she serves as a nurturing, empathetic presence in Annie’s life, often bridging the gap between Warbucks’ stern nature and Annie’s optimism. Female-presenting, to play 25 – 35. Range: G5 – Bb3

ORPHANS – Despite their circumstances, the orphans are all spirited, resilient children who face hardship with humor, mischief, and unwavering hope. Though they bicker and tease one another like siblings, they share a deep bond of loyalty and dream of finding love and belonging beyond the orphanage walls. All female-presenting children to play 6 – 12.

Duffy – Tough, loyal, oldest, and most protective

Pepper – Bossy, bold, mischievous, and a natural ringleader.

Molly – The youngest, sweet, innocent, and most trusting

Kate – Shy, gentle, quiet, and soft-hearted

Tessie – Dramatic, emotional, loves attention and flair

July – Quietly rebellious, sarcastic, independent thinker.

ENSEMBLE ROLES (To also play various roles as Hooverville citizens, NYC tourists and sellers, servants, etc.)

Bert Healy – a charismatic radio personality whose polished charm masks a sharp awareness of how to captivate an audience and shape public morale

Franklin Delano Roosevelt – A confident and reassuring leader who projects steady optimism while carefully weighing the challenges facing the nation

Drake – Warbucks’ composed and efficient chauffeur, observant and discreet, with a quiet sense of humor beneath his formal exterior

Mrs. Pugh – The Warbucks household’s firm but fair housekeeper, practical and organized, who keeps everything running smoothly behind the scenes

Star-to-Be – A determined young performer driven by ambition and a relentless belief that her big break is just around the corner