Anna Caldwell is a Chicago-based singer, producer and writer.

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Up Next: The View From Here

Nov. 21st 7:30PM - The CheckOut Chicago

Birthday Cabaret & NAMI Chicago Fundraiser

Tickets

About Anna

Anna Caldwell (she/her) is a Chicago-based soprano, producer, and writer whose work spans opera, operetta, musical theater, and original cabaret. She has performed more than 30 roles across the Midwest and internationally, appearing with companies including Chicago Fringe Opera, The Gilbert & Sullivan Opera Company of Chicago, and Ohio Valley Summer Theater. Her performance work ranges from mainstage productions to concert tours in Italy and appearances with the Cleveland Orchestra Chorus and the national tour of Star Wars in Concert.

In addition to performing, Anna is a producer and creative collaborator, developing original theatrical cabarets and devised work. She is a writer and content manager, with editorial work featured in Yahoo Finance, MSN, AOL, and major news outlets across the United States.

She is a founding member of the award-winning vocal group The Peppermint Patties, a genre-fluid ensemble known for its cabarets and gig work throughout Chicago and the Midwest.

See Full Bio

They’re joined by the lovely and graceful Anna Caldwell, as Gianetta, and Grace Ryan, as Tessa, the two newlywed wives of the handsome leading Gondoliers. These four accomplished singers make the rafters ring with their glorious voices.

—Chicago Theater Review
Gianetta (Anna Caldwell, who is superb) and Tessa (Grace Ryan, in a wonderful debut with the company)...are captivating with their vocal power and lush sound.

—Evantston Round Table
The large cast is led by Anna Caldwell, an impassioned and shining Emily.

—Cleveland.com
Anna Caldwell can sing anything. Everyone in Chicago knows this. She sings all seven of her octaves in this thing and lands a Christmas Always Finds Me that you will never forget. Anna tells our current collective story with this song, and it is beautiful and heart-rending.

—Aaron Hunt, theater critic
Ms. Caldwell enchants with a most gorgeous rendition of the ballad ‘The Sun, Whose Rays Are All Ablaze.’… Matched by tenor Tejas Gururaja, this pair dazzle with their melodramatic comedy, solos and duets.

—Chicago Theater Review

November 21st 7:30 PM

The View From Here
A coming-of-age cabaret for a 40-year old theater kid.

The CheckOut Chicago
November 21st 2026
7:30 PM

Buy Tickets!

Join Anna Caldwell and special guests for a whimsical cabaret celebrating her 40th birthday!

Through songs and stories, I'll explore what it means to be a middle-aged theater kid, and how entering this phase of life reshapes your dreams, deepens your perspective, and makes you a little more comfortable with life's unanswered questions.

The evening features an original song I wrote with Michael Oldham, an original arrangement with Cody Michael Bradley, and several of my own parodies, alongside songs by Jonathan Larson, Rodgers and Hammerstein, Stephen Sondheim, Jerry Herman, Bock and Harnick, and many more.

This special performance is a fundraiser for NAMI Chicago.

All net proceeds will be donated to NAMI Chicago, the Chicago affiliate of National Alliance on Mental Illness, which provides free mental health support, education, and resources to individuals and families throughout the Chicago area.

In addition to ticket-supported giving, additional donations to NAMI Chicago can be made here.

Support NAMI Fundraiser

Production Photos

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.

Copy of 2026.03.05 GSOC The Gondoliers-06.jpg

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.

Copy of 2026.03.05 GSOC The Gondoliers-11.jpg

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.

Performance Reel

Time Stamps

With So Little To Be Sure Of from Anyone Can Whistle
I Can't Remember from Song of Singapore
Sunrise from Song of Singapore
The Sun Whose Rays Are All Ablaze from The Mikado (Reimagined)
It's a Lovely Day Today by Ella Fitzgerald
What's The Use of Wonderin' from Carousel
Light from Next to Normal
Now Marco Dear from The Gondoliers
Selections from She Loves Me
I Hate Men from Kiss Me Kate
Gimme Gimme from Thoroughly Modern Millie

Upcoming Performances

Full Calendar

The Peppermint Patties

Anna is a founding member of an award-winning vocal ensemble called The Peppermint Patties, that specializes in tight harmonies inspired by the Andrews Sisters and Golden Age Music Theater.

They perform original, theatrical cabarets and are sought after artists for gigs, private parties and corporate events.

Learn More

Anna Caldwell is a Chicago-based singer, producer and writer.

Up Next: The View From Here

Nov. 21st 7:30PM - The CheckOut Chicago

Birthday Cabaret & NAMI Chicago Fundraiser

About Anna

They’re joined by the lovely and graceful Anna Caldwell, as Gianetta, and Grace Ryan, as Tessa, the two newlywed wives of the handsome leading Gondoliers. These four accomplished singers make the rafters ring with their glorious voices.

Gianetta (Anna Caldwell, who is superb) and Tessa (Grace Ryan, in a wonderful debut with the company)...are captivating with their vocal power and lush sound.

The large cast is led by Anna Caldwell, an impassioned and shining Emily.

Anna Caldwell can sing anything. Everyone in Chicago knows this. She sings all seven of her octaves in this thing and lands a Christmas Always Finds Me that you will never forget. Anna tells our current collective story with this song, and it is beautiful and heart-rending.

Ms. Caldwell enchants with a most gorgeous rendition of the ballad ‘The Sun, Whose Rays Are All Ablaze.’… Matched by tenor Tejas Gururaja, this pair dazzle with their melodramatic comedy, solos and duets.