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It Shoulda Been You!

Wakefield Repertory Theater proudly announces auditions for the area premiere of the new musical “It Shoulda Been You!”


Wakefield Repertory Theatre is thrilled to bring our spring 2017 production to our stage. The charming, funny and original new musical, It Shoulda Been You invites you to a wedding day that you'll never forget, where anything that can go wrong does, and love pops up in mysterious places. The bride is Jewish. The groom is Catholic. Her mother is a force of nature. His mother is a tempest in a cocktail shaker. And, when the bride's ex-boyfriend crashes the party, the perfect wedding starts to unravel faster than you can whistle "Here Comes the Bride!" It's up to the sister of the bride to turn a tangled mess into happily ever after in this musical comedy for anyone who ever had parents.

A non-stop, 90-minute laugh-riot, It Shoulda Been You is a guaranteed crowd-pleasing hit. This is a true ensemble show, featuring a dozen standout roles from old to young, making it a terrific choice for theatres wanting to feature their outstanding talent.


  • Audition Info
  • Characters
  • Staff

Auditions March 5th and 6th at 7PM
Where Wakefield/Lynnfield Methodist Church, 273 Vernon St, Wakefield, MA 01880
Callbacks March 8th
Performances May 19th-28th

To audition please prepare 32 measures of a contemporary musical theatre piece (Preferably not from ‘It Shoulda Been You’).
Callbacks will be by invitation only and will feature cold reading and vocal selections from the show.

Rehearsals will be held Sunday/ Tuesday and Thursday's

Albert Gender: Male Age: 35 to 55The wedding planner. Albert is an acerbic and delightful comic role. Always prepared for any and every possibility, this is a wedding sure to test his well-honed skills. Albert is featured throughout the show and has a wonderfully comic number called ‘Albert’s Turn’.
Annie Sheps Gender: Female Age: 25 to 30Annie is the co-maid of honor and best friend of the bride. She is friendly with Greg and together they combine their toasts into an over the top satire of 80’s power ballads. Annie also shares in a secret that bring about a big plot twist… Originated on Broadway by an African-American woman, however the role of Annie open to all races.
Brian Howard Gender: Male Age: 25 to 30Brian is the groom and is hoping the wedding will go off without a hitch. He has a tense relationship with his father and has always been a bit of a mama’s boy.
George Howard Gender: Male Age: 40 to 65Father of the groom. George is concerned about the family name and fortune and puts his already strained relationship with his son to the test when he demands the bride signs a prenup.
Georgette Howard Gender: Female Age: 40 to 65Mother of the groom. Georgette is a society lady who is dreading seeing her baby boy get married. She drowns her sorrows in boozes, backhanded compliments and memories of when Brian was a child.
Greg Madison Gender: Male Age: 25 to 30Greg is the Best Man and best friend of the Groom. He is friendly with Annie and together they combine their toasts into an over the top satire of 80’s power ballads. Greg also shares in a secret that brings about a big plot twist…
Jenny Steinberg Gender: Female Age: 30 to 35Co-maid of honor and bride's older sister. Jenny is a juicy role for a plus-sized actress. Overlooked by her family, Jenny has accepted her duties as the plain-looking sister but longs to be seen as beautiful. She is strong, feisty and goes on a journey of acceptance and growth throughout the course of the show. She has multiple show stopping moments.
Judy Steinberg Gender: Female Age: 55 to 65Mother of the bride. Judy is a strong, overbearing mother who does not mince words and loves her children… if only they would listen to her. Her nerves are tested by her daughters soon to be in-laws and is not good at playing “nice”. Beneath her tough exterior Judy also has a love of family and a heart of gold. She has several show-stopping moments.
Marty Kaufman Gender: Male Age: 30 to 35Bride's ex-boyfriend who Jenney calls by accident and he rushes to the wedding uninvited causing the family to worry that he is going to try and stop the wedding. Marty is a great role for a comedic actor who also has heart. He is one of many twists in the show as his intentions do throw the wedding plans awry.
Mimsy/ Aunt Sheila Gender: Female Age: 35 to 55Mimsy is a waiter at the hotel and one of Abert’s assistants & bride's aunt. Aunt Sheila is the over the top aunt of the steinbergs. She’s a many eater, flashy dresser and the hot mess of the wedding.
Murray Steinberg Gender: Male Age: 45 to 65Father of the bride. He is a kind man who is used to being overshadowed by his wife’s large personality. Murray is an affable man of good humor who loves his family and is trying to ensure the wedding goes off well.
Rebecca Steinberg Gender: Female Age: 25 to 30The bride. Rebecca is a bit high strung on this day of days but is determined to see the wedding go through without a hitch. Under the surface she guards several secrets which threaten to erupt at any moment and ruin the wedding. She is a kind, young woman who is uncertain of her future and what will make her happy. She is featured throughout the show and has an defining 11 o’clock moment.
Walt/uncle Morty Gender: Male Age: 45 to 55Walt is a waiter at the wedding and one of Albert’s assistanst & Morty is bride's senile uncle.

Directed by Adam Schuler

Stage Managed by Monica Bruno