Southside native Gregory Stewart brings a captivating and dynamic sound to R&B, Jazz, and Soul. Still, in his twenties, he has performed for many audiences ranging from Osaka, Japan, weddings in Barbados, and his hometown of Chicago.
Since returning to Chicago, Gregory has begun to establish his roots as a professional entertainer performing at various venues throughout the Chicagoland area. In addition, he has established himself as a cross-cultural entertainer that appeals to a wide range of audiences with his renditions of historical artists that have made indelible marks in the music industry.
Stewart’s expansive and thrilling range helped him land the role of Philip Bailey in the recent Black Ensemble Theater tribute show Reasons: A Tribute to Earth, Wind & Fire. The Chicago Tribune‘s music review called Stewart a ‘tour de force.’ His show-stopping rendition of “Fantasy” was worth the price of admission.
As Gregory establishes his roots as a professional entertainer, he’s a staple at the Untitled Supper Club, where he has performed a tribute to Nat King Cole and showcased his vocals singing covers of many popular male vocalists and groups.
N’DIGO is thrilled to chat with Gregory and see what’s next for him, and the universe prepares him to be Chicago’s next music star!
N’DIGO: Where were you born, and when did you start singing?
Does anyone in your family sing?
Gregory Stewart: I was born in the Southside of Chicago and was always singing since I was a young child. Like almost every singer out there, I started singing in the church, and I believe my first solo was at six years old. Nobody else in my close family sings, but they can hold a note. My grandmother used to sing when she was younger, so I feel I get it from her.
When did you know that you had a passion for singing?
I knew I had a passion for singing when I was in grade school. I did a talent show and sang “The Closer I Get to You by Luther Vandross, and when the crowd applauded me, I knew that I wanted to do this for the rest of my life.
Do you have any musical training? Attend a performance college, perhaps?
I was blessed to have multiple styles of training. From classical to choral to gospel, I learned it all. I also did music theory when I was in high school. I stayed in choir all of my education years. So my training from my instructors has been beneficial in my career.
Where did you hone your skills?
I started to hone my skills when I would go to open mic nights at Refuge Live in the South Loop. It was a safe space where I was able to take risks and find my true voice. I learned how to interact with the crowd and learn how to put on a performance, and I am so grateful for them.
How important is it to have your family’s support?
It’s extremely important. My family is my rock. They have been supporting me since I was a baby. Literally, I have four older sisters, and they all play an important part in my career. I probably would not have gone this far without them if I did not have had them. My mother’s love and support are undeniably sent from God. I’m just really blessed to have them.
Tell me about your music experience in China. How did that come about?
A friend of mine told me about Universal Studios in Japan, Osaka. They were telling me that I must audition. So I did and was cast. I was there from February 2018 to February 2020. It was an experience that I will never forget. I was doing what I loved in a different country. The culture is so beautiful, and to experience a different culture than mine was very beneficial to me.
What did you take away from that experience? And what did you learn about yourself?
It was there that I gained the stamina and endurance to perform. We were doing four to five shows daily, five days a week outside in all seasons. I was singing and dancing to hundreds and thousands of people daily, which was amazing. I went away from that experience knowing God had me at the right place at the right time.
So, you came back to Chicago from Osaka, Japan, and have been working ever since. Tell N’DIGO readers about what you have been doing.
Well, I came back during the pandemic, and I was really just doing what everyone else was doing, staying home and working from home. Then when things got better, I started to do more of my own personal shows at different venues such as Untitled Supper Club, Tavern on LaGrange, and many more.
I was then sought out by this band I regularly sing with as the co-lead singer, Maggie Speaks. I’ve been performing with them for two years now.
Recently I stepped back into my theater world and was cast in Reasons: A Tribute to Earth, Wind & Fire as Philip Bailey at the Black Ensemble Theater. This show has been a true blessing to me and my career. We had the pleasure of meeting Verdine White and got his stamp of approval for the show. So it’s been great thus far.
What advice would you give aspiring singers/actors trying to make it in the music business?
Know your worth. Study and enhance your craft enough that people will never deny your talent. Most importantly, appreciate every moment because God can and will take things away if we don’t appreciate them.
Why Chicago? Do you think the other markets (LA, New York, Nashville) are over-saturated?
Chicago has been all I’ve known. I grew up in Chicago, which has taught me much about entertainment. I always say that if you can make it in Chicago, you can make it anywhere. New York and LA will always be there,, and I see myself going there for work. But when God says I’m ready for it, ill be making my way there. But I still have some work to do here in Chicago.
What’s your favorite affirmation?
I am in the right place at the right time, doing the right thing!
Best advice ever given to you?
It’s not about you but for God. Always be humble enough to let God use the gift that He gave you to make room for you so He can be glorified.
What’s your favorite Chicago restaurant?
Provare is by far the best black-owned restaurant in Chicago! Hands down!
What do you do for self-care?
Rest, rest, and more rest. If I don’t have a day of work or performing, I try to get as much rest as possible. Sleep is my best friend! It also helps preserve the vocal cords, so that’s always great!
Where do you see yourself in 5 years? What’s next for Gregory Stewart?
In the next five years, I see myself even more successful in the theater world. I hope to do more film work but, most importantly, have my own music out and thriving everywhere. I just want to make music and continue to bless people with the gift that God gave me.
Where can N’DIGO’s readers follow or find you?
You can follow me on Instagram @gregorystewartjr_ as well as Facebook Gregory Stewart Jr. I post all of my show dates and more information on those pages.
