Anna Caldwell
Anna Caldwell (b. 1986; she/her) is a Chicago-based soprano, writer, and senior marketing associate 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 engagement.
Recent roles include 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.
In Spring 2026, she returns to the role of Gianetta in The Gondoliers with The Gilbert and Sullivan Opera Co. of 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.
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, travelling, hiking, camping, reading memoirs and studying Italian and — after several dye jobs and hair cuts in recent years — will remain a committed redhead until she is too tired to keep covering up the grays (shhhhhhh.)
Marketing Inquiries: www.caldwellmediaarts.com
Instagram: @thesleepysoprano
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 engagement.
Recent roles include 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.
In Spring 2026, she returns to the role of Gianetta in The Gondoliers with The Gilbert and Sullivan Opera Co. of 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.
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, travelling, hiking, camping, reading memoirs and studying Italian and — after several dye jobs and hair cuts in recent years — will remain a committed redhead until she is too tired to keep covering up the grays (shhhhhhh.)
Marketing Inquiries: www.caldwellmediaarts.com
Instagram: @thesleepysoprano