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Who is Roberta Miles?

Roberta was trained as an opera singer. She began her professional jazz career when she was hired to sing at Club Mon, a glamorous Japanese nightclub on the third floor of Chicago’s Playboy Club. Her set of popular Japanese hits (which she sang phonetically) was interspersed with American jazz classics. It didn’t take long for her to get hooked – she switched her focus from opera to jazz, and never looked back.

“A sultry stylist”
— June Sawyers, The Chicago Tribune

Miles recorded her album, Body and Soul, with producer Dean Rolando. She has worked with some of Chicago’s most talented jazz musicians – artists such as Bob Moreen, Jim Cox, Neal Seroka and Charles McFarlan.

Chicago artist, Roberta Miles, is a graduate of the American Academy of Art. Currently Miles teaches Art after Dark at Dewey School in Evanston. As a teacher at The Art Center of Highland Park, where she worked as an art teacher for 18 years, she also served as the teacher liaison on the board of directors. Miles is the founder of “Young at Art,” a program for bringing art to seniors. She is part of the teaching staff at Evanston Art Center in Evanston, Illinois.Roberta Miles is an accomplished jazz singer, with a degree in Opera Performance. She received the Illinois Collegiate Entrepreneur Award in 1997, and is listed in Who’s Who of America in 2000, and Biltmore Who’s Who in 2007-2008. Miles is also known for her writing and performance work. Her credits also include writing and performing for Steppenwolf Theatre in Chicago. She produces two long time running shows in Chicago; Loose Chicks and Cafe Cabaret. Miles has also written and performed two off color solo shows based on the richness of her life.
ROBERTA MILES’ award-winning autobiographical monologues touch on growing up in Chicago in the 70’s and her life’s indiscretions and romantic regrets.

Roberta chronicles her quest for mental and physical health with brutally hilarious candor. She has crafted her monologues into the one-woman show, I Want a Banana, and Other Desperate Love Stories, which she has performed at Strawdog Theatre and BoHo Theatre.

As the co-creator and producer of Loose Chicks and producer of Cafe Cabaret, Roberta continues to push the envelope with a wide range of memorable performances.

Loose Chicks is a collective of courageous women who share experiences that most women keep to themselves. Each show features exceptional writers and performers who allow themselves to be vulnerable as they share with uncommon honesty.

Cafe Cabaret is a classic variety show featuring dance, comedy, storytelling, music and more. We feature a rotating cast of Chicago favorites and new talent. From poignant to funny, mirth to disaster, and everything in between, Cafe Cabaret promises an electric night of eclectic entertainment.

Roberta also produces A Gathering of Outrageous Souls, an event to benefit the MS Society.

A Gathering of Outrageous Souls is an afternoon full of creativity and bounty. It’s a come as you are and when you please event featuring entertainment by some of the city’s most engaging comedians, musicians and dancers, an exciting live auction of premium items from local businesses,  and an Artisan Market with one of a kind goods and services from local artists.

What does Roberta do?

To find out more about the different events & shows Roberta produces, her art, or her music, visit the sites below.


cafe cabaret

Contact Roberta Miles

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