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Hey, I’m

Jessica 
Caldwell

Actor / Singer / Dancer

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About Me

I am a singer, actor, and dancer based in NYC and originally from Portland, OR.  My love for performing started at a young age. I loved playing make believe, coming up with skits and dances and forcing every adult (and child) to watch me perform them. My grandpa kindled my love for theatre by showing me every old MGM movie musical, especially anything with Judy Garland. Disney princess movies had me in a chokehold, and after I saw The Phantom of the Opera, I was hooked (I may or may not have gone through 6 CDs of the movie cast before I turned 9).

While I love Golden Age theatre, I believe the shows were written with strong male characters and not always strong, independent female characters. I want to take those roles, which were written to support a male through line, and give them the power and growth that they deserve.  If I'm not performing or at rehearsal, I can be found trying new restaurants and recipes. I'm a huge foodie! My big fixations right now are running (I'm training for a half marathon), reading (Mysteries and Thrillers are my go to), and podcasts (usually of the true crime variety). 

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What's New?

A Fiddler on the roof, sounds crazy, no?

I'm so excited to be back at The Fireside in Fort Atkinson, Wisconsin doing Fiddler on the Roof! I am playing the dear Grandma Tzeitel and getting to change marriage arrangements 7 times a week! We just opened on February 29th and we run until April 14th. I love my cast and creative team so much and I'm honored to tell this classic and touching story with them.

What's New?

Videos

Showreel

Photos

Photos

Reviews!

​"Such songs from the show as “Everything is Coming Up Roses” and “Let Me Entertain You” have become well known on their own, and Woodminster doesn’t disappoint with Deborah Del Mastro (Rose) doing a knockout version of the former and Jessica Caldwell (Gypsy) lending her beautiful soprano to the latter." (Sally Hogarty, Gypsy at Woodminster Summer Musicals)

 

"Caldwell, while beautiful as Gypsy Roses Lee, gives her most heartfelt performances as her younger self with an especially poignant rendition of 'Little Lamb.'" (Sally Hogarty, Gypsy at Woodminster Summer Musicals)
 

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