Auditions: Annie and Diary of A Wimpy Kid!

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 16th and 18th, from 6 p.m until 10 p.m.

Video audition submissions will be accepted until Tuesday, March 17th, 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 6 adult actors, and 14 student actors (including swings). Most ensemble roles will double in some fashion. 

Adult Roles – 

FRANK HEFFLEY Male Greg’s put-upon father, who possesses an interest in U.S. history and a deep distrust of teenagers. Uncomfortable speaking with tweens, Frank is always trying to toughen Greg up and get him to “go be active,” perhaps in an effort to keep his son from following in his own wimpy footsteps. Strong, comedic performer and singer.

SUSAN HEFFLEY Female Greg’s chipper, loving, and overly-supportive mother, Susan is a former Pre-school teacher who is constantly looking for “teachable moments” with her boys. Though she always sees the best in her kids (sometimes blinding her to reality), she is also quick to become the household disciplinarian when necessary. Strong, comedic performer and singer.

MR. WINSKY/BILL WALTER  – MALE IDENTIFYING, ANY ETHNICITY Plays: MR. WINSKY Faculty advisor of the school’s ‘Safety Patrol.’ He takes his job super seriously, as though he’s head of the FBI or Special Ops. BILL WALTER 35 year-old, unemployed rocker dude who still lives with his folks and plays in Rodrick’s high school band, Löded Diper. Strong, comedic performer and singer.

MRS. CLAYTON/FREGLEY’S MOM – FEMALE IDENTIFYING, ANY ETHNICITY Plays: MRS. CLAYTON Greg’s no-nonsense English teacher. Loves to host the Winter Talent Show every year. FREGLEY’S MOM A creepy, frail, and occasionally terrifying elderly woman. She could be a ghost. Strong, comedic performer and singer

Student Roles – 

Greg Hefley – Male – 11 year-old, first year middle-schooler, driven with a burning desire to achieve popularity and acclaim at any and all costs. Equal parts cocky and insecure, Greg’s single-focus on popularity often makes him short-sighted and immature, almost costing him his closest friendship. Strong, comedic young performer with a powerful, unchanged singing voice.

Rowley Jefferson – Male – 11 year-old, first year middle-schooler, with a determinedly sunny disposition and über positive outlook on life. Almost blindly devoted to Greg, but ultimately capable of standing up for himself. Strong, comedic young performer with a powerful, unchanged singing voice.

Rodrick Hefley – Male – Sullen, sarcastic 16 year-old, older brother of Greg, and his main tormentor. Brash and obnoxious, Rodrick is the front-man of the heavy-metal, garage band; Löded Diper and delights in torturing Greg and taxing their parents goodwill. Strong, comedic young performer with a powerful, singing voice.

Manny Heffley – All Genders –  Impossibly adorable and spoiled baby brother of Greg and Rodrick. Manny enjoys exalted status as his parents dote on him and make constant excuses for his behavior. Strong comedic young performer of any gender, to portray a toddler.

Chirag Gupta –  Male – Greg’s quick-witted and wily classmate, who is enthusiastically engaged in a years-long prank-battle with Greg. Strong, comedic young performer with a powerful unchanged singing voice.

Patty Farrell –  Female – Ambitious, driven, and overachieving classmate of Greg. Always out to best him at every turn since he poured glitter-glue down her back in second grade, Patty sees success as the only destination. Strong, comedic young performer with a powerful singing voice.

Fregley –  Male – Greg’s deeply odd-ball classmate, who is sensitive to sugar and unapologetically interested in his own boogers. Strong, comedic young performer with a powerful, unchanged singing voice.

Bryce Anderson – Male – Dreamboat classmate of Greg’s, who enjoys unfettered adoration and popularity. Infamous for his cutting remarks and cute-butt status, Bryce has hit his growth-spurt early and presents as more mature than many of his peers. Strong, comedic young performer and singer.

Joshie –  Female/Male –  European teen pop star and Rowley’s idol. A cross between a boy-band star and KidsBop performer, Joshie is obviously manufactured to make responsibility sound cool to 6-8 year old girls. His motto: follow your dreams and respect your parents! Strong, comedic young performer and singer with pop chops.

Chris/Christine Hosey & Lionel/Leona James – Female/Male – Two of the most unpopular and nerdy kids in Middle School. Strong, comedic young performer and singers.

Paulene & Yvette –  Female –  Patty Farrell’s minions. They like what she likes and dislike whatever she dislikes – aka Greg. They are perfect in every way, but always look up to Patty. Strong, comedic young performer and singers.

Claire –  Female –  A ‘Wednesday Addams’-lite, goth-in-training middle schooler. Claire is the keeper of the lore of the Cheese Touch and takes it upon herself to make sure nobody starts the dreaded curse again. Strong, comedic young performer and singer.

ANNIE Character Breakdown

We are able to cast a company of 14 adult actors and 8 student 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

AUDITION FORM