About Anna

Anna Caldwell is a Chicago soprano, producer, and writer known for work that bridges classical singing and theatrical storytelling. She performs throughout Chicago and the Midwest as a soprano soloist in opera, operetta, and musical theater, while also creating and producing original cabarets and devised performance work.

Anna’s Story

Anna Caldwell (she/her) is a Chicago-based soprano, producer and writer whose stage credits span more than 30 roles in opera, operetta, and musical theater across the Midwest.

Anna has performed with Chicago Fringe Opera, Belissima Opera, The Savoyaires, The Gilbert & Sullivan Opera Company of Chicago, Janus Concert Series (inactive), Actor’s Moveable Theater, Ohio Valley Summer Theater, The Genesis Theater Project, and Mercury Theater Company, among others.

Her concert and gig work includes appearances with The Caroling Party, Opera Inter Alia, Working in Concert and other Chicago-based ensembles and churches. She has also sung internationally on concert tours with Musica nelle Marche in Italy, performed with the Cleveland Orchestra Chorus, and appeared in the national tour of Star Wars in Concert during its Cleveland, Cincinnati and Pittsburgh engagements,

Recent roles include Gianetta in The Gondoliers with The Gilbert and Sullivan Opera Co. of Chicago, The Narrator in Joseph and the Amazing Technicolor Dreamcoat and Kate in Kiss Me, Kate at The People’s Bank Theater in Ohio; Krysia in Jake Heggie’s Two Remain with Chicago Fringe Opera; and Rose in Song of Singapore in Athens, Ohio.

Anna is a founding member of the award-winning vocal group, The Peppermint Patties a genre-fluid ensemble that produces it’s own shows and is highly sought after for gigs and events in Chicago and the Midwest.

This fall she will debut her first solo show, The View From Here an unabashedly personal cabaret about embracing midlife, with original songs and lyrics in collaboration with Michael Oldham on November 21st at The CheckOut in Chicago.

Offstage, Anna is a business manager, script writer, prop maker, arranger and jill-of-all trades for The Peppermint Patties — where she typically sings the top line harmony. She also works full-time as a Senior Content Marketing Associate for a Finance Company and is an SEO-trained copywriter. Her editorial work has been featured in outlets including Yahoo Finance, MSN, AOL, and regional and national news publications such as the Miami Herald, Lexington Herald-Leader and Charlotte Observer.

She lives in the Uptown neighborhood of Chicago with her partner, Ross, and their cats, Gustav and Matthew. When not performing or writing, she enjoys watching Star Trek, traveling, hiking, camping and reading memoirs. After several dye jobs and hair cuts in recent years she will remain a committed redhead for the foreseeable future.

See Full Resume

A woman singing on stage with a microphone, wearing a red blazer and dark sparkly pants, in front of purple curtains.

Actors on stage performing a scene dressed in historical costumes, with a man and woman smiling and holding hands, surrounded by other performers.

Two actors performing on stage in costumes, with a backdrop resembling a house with a wooden door and stone chimney, during a theatrical play.

Scene from a theatrical play featuring a man in elaborate historical costume and women dressed as fairies or spirits with wings and colorful costumes.

A man and a woman dressed in vintage clothing celebrating on stage with their hands raised, during a lively event.

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Theatrical stage performance with a group of women dressed in costumes resembling laundry, some kneeling and some standing, while musicians and a conductor are in the background.

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A theatrical performance scene with a woman standing at the center, speaking to children seated on the floor. The woman has red hair and is wearing a black dress and a long, sparkling, gold coat. The children are dressed in blue shirts and are lookin

Two women dressed as fairies or magical characters dancing happily on stage with a backdrop of trees and other performers.

A group of women on stage, with one woman in the center singing into a microphone, dressed in casual summer clothes with a dark background.

A theatrical stage performance with multiple actors in costume, performing a dramatic scene with a background that resembles an outdoor landscape with hills and trees.

Stage performance with actors in vintage 1950s-style dresses and striped shirts, some wearing hats, standing in a row during a theatrical show.

Three women dressed in brown costumes with head coverings, standing barefoot on stage, with a person playing a guitar in the background, during a theatrical performance.

A woman singing passionately in a vintage-style red dress, with a band playing in the background.

Stage scene with a woman singing or speaking, wearing a long sequined coat, surrounded by young people in blue shirts sitting cross-legged, with a blue backdrop.

Actors on stage performing a scene from a play with medieval or renaissance costumes, including women in long dresses and men in red uniforms with black hats, in front of a backdrop depicting a stone building and a set piece resembling a gallows or a

The image shows a theatrical stage with actors, including a woman with red hair, white sunglasses, and colorful clothing, and a man wearing a large fruit basket hat and casual attire, performing in a scene with an audience of children in the backgrou

A man playing a ukulele and a woman in a red dress performing on stage with a band and percussion instruments in the background.

Three older adults singing on stage in tropical-themed party costumes, with a band playing in the background.

Group of performers on stage during a theatrical production. One man dressed as an Egyptian Pharaoh in the center, holding hands with a woman in a gold and black outfit, while others sing or speak in the background.