Anna Caldwell
Latest News on Anna Caldwell:
The Peppermint Patties to Celebrate the Holiday Season With Two Shows in Chicago (Nov 25, 2025)
SING, SING, SING! CHICAGOLAND! With The Peppermint Patties to be Presented at Hey Nonny (Jul 8, 2025)
4th Annual International Women’s Day Concert to Take Place in Oak Park (Jan 28, 2025)
The Peppermint Patties to Celebrate the Holiday Season With Two Shows in Chicago (Nov 25, 2025)
SING, SING, SING! CHICAGOLAND! With The Peppermint Patties to be Presented at Hey Nonny (Jul 8, 2025)
4th Annual International Women’s Day Concert to Take Place in Oak Park (Jan 28, 2025)
BIO
Anna is a founding member of The Peppermint Patties, a professional jazz vocal trio. She performs regularly with Chicago-based companies and recently debuted with Chicago Fringe Opera in the city's premiere of Jake Heggie and Gene Sheer's Opera, Two Remain. She has performed in Italy with Musica nelle Marche. Regional credits include roles with The Genesis Theater Project, Ohio Valley Summer Theater, Mercury Summer Stock, and Actor's Moveable Theater.
Some past roles include Rose (Song of Singapore), Elsie (Yeoman of the Guard), Bessie u/s (Merrie England), Guenevere u/s (Camelot), Amalia (She Loves Me), Cinderella (Into the Woods), Adele (Die Fledermaus), Lily (Secret Garden), Marian (The Music Man), Giulietta (I Capuleti e i Montecchi), Emily (Our Town; the opera), Eurydice (Orphée aux enfers).
STAGE CREDITS
News
The Peppermint Patties to Celebrate the Holiday Season With Two Shows in Chicago
by Chloe Rabinowitz - Nov 25, 2025
The Peppermint Patties are ringing in the holidays with two very different live performances this December in Chicago. The season begins with A Christmas Carol Cabaret, a playful re-imagining of Dickens' classic tale told by the Patties.
by Chloe Rabinowitz - Nov 25, 2025
The Peppermint Patties are ringing in the holidays with two very different live performances this December in Chicago. The season begins with A Christmas Carol Cabaret, a playful re-imagining of Dickens' classic tale told by the Patties.
SING, SING, SING! CHICAGOLAND! With The Peppermint Patties to be Presented at Hey Nonny
by Chloe Rabinowitz - Jul 8, 2025
One night only The Peppermint Patties will return to Hey Nonny for a Chicago themed cabaret featuring local talent. Learn more and see how to attend here!
by Chloe Rabinowitz - Jul 8, 2025
One night only The Peppermint Patties will return to Hey Nonny for a Chicago themed cabaret featuring local talent. Learn more and see how to attend here!
4th Annual International Women’s Day Concert to Take Place in Oak Park
by Chloe Rabinowitz - Jan 28, 2025
On Saturday, March 8, 2025, beginning at 7:30 PM, award-winning female singers are centerstage for the 2025 International Women’s Day concert. Learn how to attend.
by Chloe Rabinowitz - Jan 28, 2025
On Saturday, March 8, 2025, beginning at 7:30 PM, award-winning female singers are centerstage for the 2025 International Women’s Day concert. Learn how to attend.
A CHRISTMAS CAROL CABARET Announced At Hey Nonny Live Music + Kitchen
by A.A. Cristi - Nov 13, 2024
Experience a festive evening with The Peppermint Patties in Arlington Heights as they present A CHRISTMAS CAROL CABARET. Enjoy close vocal harmonies and holiday classics inspired by Charles Dickens' tale.
by A.A. Cristi - Nov 13, 2024
Experience a festive evening with The Peppermint Patties in Arlington Heights as they present A CHRISTMAS CAROL CABARET. Enjoy close vocal harmonies and holiday classics inspired by Charles Dickens' tale.
The Peppermint Patties Return to The Venus Cabaret Theater
by Stephi Wild - Aug 29, 2024
One night only The Peppermint Patties return to The Venus Cabaret Theater for a Chicago themed cabaret featuring local talent.
by Stephi Wild - Aug 29, 2024
One night only The Peppermint Patties return to The Venus Cabaret Theater for a Chicago themed cabaret featuring local talent.
The Peppermint Patties to Return to The Venus Cabaret Theater and Hey Nonny Live Music + Local Kitchen
by Chloe Rabinowitz - Nov 10, 2023
Get ready for two unforgettable evenings of holiday music and fun with The Peppermint Patties at The Venus Cabaret Theater and Hey Nonny Live Music + Local Kitchen. Christmas with The Peppermint Patties features special guests The Feathered Beaus and pianist Michael Oldham.
by Chloe Rabinowitz - Nov 10, 2023
Get ready for two unforgettable evenings of holiday music and fun with The Peppermint Patties at The Venus Cabaret Theater and Hey Nonny Live Music + Local Kitchen. Christmas with The Peppermint Patties features special guests The Feathered Beaus and pianist Michael Oldham.
The Peppermint Patties Present SING, SING, SING! A Summer Cabaret At The Venus Cabaret Theater
by A.A. Cristi - Aug 1, 2023
The Peppermint Patties present their summer cabaret special, Sing, Sing, Sing! at The Venus Cabaret Theater. The show combines various genres and features reimagined Andrews Sisters covers, jazz standards, musical theater favorites, retro hits, and more.
by A.A. Cristi - Aug 1, 2023
The Peppermint Patties present their summer cabaret special, Sing, Sing, Sing! at The Venus Cabaret Theater. The show combines various genres and features reimagined Andrews Sisters covers, jazz standards, musical theater favorites, retro hits, and more.
Celebrate Valentine's Day With The Peppermint Patties At Borelli's Restaurant
by A.A. Cristi - Feb 10, 2023
Join The Peppermint Patties for dinner and a show as they perform 'Won't You Be My Galentine? An Evening of Love Songs at Borelli's Restaurant.
by A.A. Cristi - Feb 10, 2023
Join The Peppermint Patties for dinner and a show as they perform 'Won't You Be My Galentine? An Evening of Love Songs at Borelli's Restaurant.
CHRISTMAS WITH THE PEPERMINT PATTIES- A Heartwarming Holiday Concert Announced At Venus Cabaret
by A.A. Cristi - Nov 4, 2022
Enjoy a heartwarming evening of holiday music with The Peppermint Patties! Their 90-minute show features close harmony arrangements of your favorite Christmas songs like White Christmas, Jingle Bells, and Cool Yule, as well as jazz standards, retro hits, a cappella numbers, and musical theatre favorites.
by A.A. Cristi - Nov 4, 2022
Enjoy a heartwarming evening of holiday music with The Peppermint Patties! Their 90-minute show features close harmony arrangements of your favorite Christmas songs like White Christmas, Jingle Bells, and Cool Yule, as well as jazz standards, retro hits, a cappella numbers, and musical theatre favorites.
The Peppermint Patties Return To Chicago With Summer Show at the Venus Cabaret Theater
by Stephi Wild - Jul 7, 2022
The Peppermint Patties return to Chicago with a lineup of classic close harmony arrangements including reimagined Andrews Sisters covers, jazz standards, retro hits, acapella numbers, musical theater favorites and more.
by Stephi Wild - Jul 7, 2022
The Peppermint Patties return to Chicago with a lineup of classic close harmony arrangements including reimagined Andrews Sisters covers, jazz standards, retro hits, acapella numbers, musical theater favorites and more.
The Peppermint Patties Bring Close Harmony Classics To Hey Nonny Stage In Holiday Cabaret
by A.A. Cristi - Nov 3, 2021
The Peppermint Patties return to the stage with a 90-minute lineup of holiday favorites and classic close-harmony hits made famous by The Andrews Sisters, Chordettes, Lennon Sisters, and more.
by A.A. Cristi - Nov 3, 2021
The Peppermint Patties return to the stage with a 90-minute lineup of holiday favorites and classic close-harmony hits made famous by The Andrews Sisters, Chordettes, Lennon Sisters, and more.
Metropolitan Room Welcomes Denise Spann Morgan & The 'Marvelous' Marvelettes Tonight
by BWW News Desk - Jul 16, 2015
The internationally acclaimed jazz cabaret Metropolitan Room and Diva Dynasty Productions is proud to present Denise Spann Morgan and The 'Marvelous' Marvelettes in Come and Get These Memories, starring Annette Bland McCoy and LaRita Gaskins, and the Diva Dynasty Band featuring Anna Caldwell (piano), Joe Ham (drums), Kim Clarke (bass), and Kevin James Perry (guitar).
by BWW News Desk - Jul 16, 2015
The internationally acclaimed jazz cabaret Metropolitan Room and Diva Dynasty Productions is proud to present Denise Spann Morgan and The 'Marvelous' Marvelettes in Come and Get These Memories, starring Annette Bland McCoy and LaRita Gaskins, and the Diva Dynasty Band featuring Anna Caldwell (piano), Joe Ham (drums), Kim Clarke (bass), and Kevin James Perry (guitar).
Metropolitan Room to Welcome Denise Spann Morgan and The 'Marvelous' Marvelettes, 7/16
by Tyler Peterson - Jul 6, 2015
The internationally acclaimed jazz cabaret Metropolitan Room and Diva Dynasty Productions is proud to present Denise Spann Morgan and The "Marvelous" Marvelettes in Come and Get These Memories, starring Annette Bland McCoy and LaRita Gaskins, and the Diva Dynasty Band featuring Anna Caldwell (piano), Joe Ham (drums), Kim Clarke (bass), and Kevin James Perry (guitar).
by Tyler Peterson - Jul 6, 2015
The internationally acclaimed jazz cabaret Metropolitan Room and Diva Dynasty Productions is proud to present Denise Spann Morgan and The "Marvelous" Marvelettes in Come and Get These Memories, starring Annette Bland McCoy and LaRita Gaskins, and the Diva Dynasty Band featuring Anna Caldwell (piano), Joe Ham (drums), Kim Clarke (bass), and Kevin James Perry (guitar).
TITUS ANDRONICUS Set for Free Performances at The Schapiro Theatre This Weekend
by BWW News Desk - Jan 10, 2014
The lamentable tragedy of TITUS ANDRONICUS by William Shakespeare will perform free shows at The Schapiro Theatre, located at 605 W. 115th Street, New York, NY. The production runs today, January 10-12, 2014.
by BWW News Desk - Jan 10, 2014
The lamentable tragedy of TITUS ANDRONICUS by William Shakespeare will perform free shows at The Schapiro Theatre, located at 605 W. 115th Street, New York, NY. The production runs today, January 10-12, 2014.
TITUS ANDRONICUS Set for Free Performances at The Schapiro Theatre, 1/10-12
by BWW News Desk - Jan 3, 2014
The lamentable tragedy of TITUS ANDRONICUS by William Shakespeare will perform free shows at The Schapiro Theatre, located at 605 W. 115th Street, New York, NY. The production runs January 10-12, 2014.
by BWW News Desk - Jan 3, 2014
The lamentable tragedy of TITUS ANDRONICUS by William Shakespeare will perform free shows at The Schapiro Theatre, located at 605 W. 115th Street, New York, NY. The production runs January 10-12, 2014.
Photo Flash: First Look at John Stiens, Jen Walker and More in Black Ship's FOREVERENDIA
by BWW News Desk - Nov 27, 2012
The Black Ship Co. announces the Chicago premiere of Foreverendia, by Brian Tuttle and directed by The Black Ship Co.'s Artistic Director Nicki Mazzocca, November 28 - December 23, at the Athenaeum Theatre's newly remodeled Studio 2, 2936 North Southport Avenue. Press night is Wednesday, November 28 at 8 p.m. The performance schedule is Thursdays through Saturdays at 8 p.m. and Sundays at 2 p.m. Tickets are $16 - $24 and are on sale now at www.blackshipco.org or by calling the Athenaeum Theatre box office at 773-935-6875. BroadwayWorld has a first look at the production below.
by BWW News Desk - Nov 27, 2012
The Black Ship Co. announces the Chicago premiere of Foreverendia, by Brian Tuttle and directed by The Black Ship Co.'s Artistic Director Nicki Mazzocca, November 28 - December 23, at the Athenaeum Theatre's newly remodeled Studio 2, 2936 North Southport Avenue. Press night is Wednesday, November 28 at 8 p.m. The performance schedule is Thursdays through Saturdays at 8 p.m. and Sundays at 2 p.m. Tickets are $16 - $24 and are on sale now at www.blackshipco.org or by calling the Athenaeum Theatre box office at 773-935-6875. BroadwayWorld has a first look at the production below.
Photo Flash: First Look at Black Ship Co's FORVERENDIA
by BWW News Desk - Oct 23, 2012
The Black Ship Co. announces the Chicago premiere of Foreverendia, by Brian Tuttle and directed by The Black Ship Co.'s Artistic Director Nicki Mazzocca, November 28 - December 23, at the Athenaeum Theatre's newly remodeled Studio 2, 2936 North Southport Avenue. Press night is Wednesday, November 28 at 8 p.m. The performance schedule is Thursdays through Saturdays at 8 p.m. and Sundays at 2 p.m. Tickets are $16 - $24 and are on sale now at www.blackshipco.org or by calling the Athenaeum Theatre box office at 773-935-6875. BroadwayWorld has a first look at the production below.
by BWW News Desk - Oct 23, 2012
The Black Ship Co. announces the Chicago premiere of Foreverendia, by Brian Tuttle and directed by The Black Ship Co.'s Artistic Director Nicki Mazzocca, November 28 - December 23, at the Athenaeum Theatre's newly remodeled Studio 2, 2936 North Southport Avenue. Press night is Wednesday, November 28 at 8 p.m. The performance schedule is Thursdays through Saturdays at 8 p.m. and Sundays at 2 p.m. Tickets are $16 - $24 and are on sale now at www.blackshipco.org or by calling the Athenaeum Theatre box office at 773-935-6875. BroadwayWorld has a first look at the production below.
FREQUENTLY ASKED QUESTIONS
How many Broadway shows has Anna Caldwell been in?
Anna Caldwell has appeared on Broadway in 1 shows.
How many West End shows has Anna Caldwell been in?
Anna Caldwell has not appeared in the West End.
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