PROFILE: Chester Gregory

Breakout Broadway star Chester Gregory is all the proof you need that dreams can become reality.

by Nancy Dunham Photography by Lenox Fontaine Styling by Douglas Hickman

Chester Gregory grew up watching Michael Jackson videos and listening to his music, soon finding his own performances winning him major praise – and standing ovations – from the King of Pop, Isaac Hayes, Phil Collins and many other luminaries.


Yet the Gary, Indiana native doesn’t credit his five-octave voice, dancing prowess or brilliant acting to his success, which includes major Broadway roles in productions ranging from The Jackie Wilson Story to Dreamgirls. In a revealing interview from his Harlem home, Gregory talks about breaking through in the entertainment business and how others can, too.


YRB: You’re native to Gary, Indiana. That’s a long way from Broadway. What inspired you to become an entertainer?

Chester: Gary is a city that really, really appreciates the arts. I went to a performing arts high school and from there I received a lot of training in three areas (music, theatre and dance). Also, Gary is the hometown of Michael Jackson [so I was inspired] just growing up, listening to Michael Jackson’s albums, watching his videos. He is a huge inspiration for the city. So for me, also having a love of the arts, I wanted to pursue them.

YRB: Were your parents very supportive?

Chester: Yes. My mother was and is an arts lover and so she took me to Chicago to see various shows (including The Wiz and Annie). When I told my parents that I wanted to be an entertainer, they were excited about it, and they supported me.

If they heard me sing and it didn’t sound good, then they would put me in voice lessons. If they saw me do a routine and the ending wasn’t good, then they would tell me that. They told me the truth, which I liked a lot. That really helped me, and it [sweetened my] feeling of success when they did praise me.

YRB: You’ve said that you’ve met some of the people you saw on stage when you were young. That had to be amazing.

Chester: Yes, I ended up meeting Stephanie Mills, Andre DeShields and other people I watched back then. Those are people I now know who paved the way for me. It was great meeting Andre DeShields – what an honor. He gave me some pointers I have applied to this day. Basically, he told me the audience is like a pack of hungry wolves. If you feed them everything all at once then they will eat you alive, but if you give them controlled portions then you stay in control. I thought that was brilliant. I went the next day and had the greatest show of my life. Since then, I have been really applying this technique.

YRB: It’s fascinating that you have a career apart from theatre as a singer-songwriter. What was your motivation to start that?

Chester: It all seemed to fall in line with me. My love for the arts pretty much runs through every area except visual arts. I’m not able to draw so I stay away from that! Along with singing and studying music, songwriting was a natural evolution. I was studying the arts so it all started with me listening to music. I think a friend of mine in college gave me a track and I played it over and over and I started to say, “This could go like this, instead.” At the time, I had a little home recorder and I [rerecorded] it. My friends said, ‘That sounds good,’ so I kept writing.

YRB: Tell us about your new album.

Chester: I’m really at the beginning stages of this new project. I’m working with a lot of people who have sold a lot of records. Dot Da Genius, who worked with KiD CuDi and is a multi-platinum producer, and 88-Keys, who has done work with Mos Def. I’m taking it back to old school. By that, I mean recording in an actual studio. I know what I want the music to sound like. I know there is so much in the world to draw inspiration from, but the sound I want to achieve comes from a raw place. I want to do a modern-day version of Stax recordings. I was on tour with Dreamgirls and got the chance to go to the Stax Museum and [revisit the recordings of] Otis Redding, Isaac Hayes and all those wonderful Stax artists. A lot of what they did was on one track. They got together in the studio, agreed what the song would be and went for it. Today, everyone is into perfecting music as opposed to going into the studio and everyone doing their part. Now, it’s easy to make it exactly perfect and tuned, but something else is missing – the soul of the music. What I am doing is going into the studio and really finding the soul for the music by living there and creating.

YRB: So you’re on Broadway and recording this new album in New York, yet you’ve done work in Los Angeles. What’s it’s like to balance the different personalities and cultures, especially between N.Y. and L.A.?

Chester: I haven’t spent much time on the West Coast, really. I mainly work in New York. Still, some of the stereotypes have some ring of truth to them. In New York, everything is now and very, very urgent. Everyone has to say exactly how they feel, and in a city very overly populated, people have a sense of desperation. A lot of people in New York are not from New York. They come to New York to make their dreams happen. In Los Angeles, people go there to make dreams come true as well – but in L.A., things are a little bit more laidback. Everything is at least a 20-minute drive away and you can get in your car and not deal with people until it’s time to. You have more power over [how much time you spend with people]. One time I was in New York and working really hard on Broadway for a year straight with no off days. As a vacation, I flew to L.A. for a few days just because it was so completely opposite of New York.

YRB: So many people would do anything to have the success you’ve achieved. Is there a misconception that keeps some people from achieving their goals?

Chester: To me, the misconception is thinking that talent is going to get you where you want to go. It takes a lot more than talent. You have to acquire skills.  You take your talent, learn what it is, find your strongest point and weakest point and showcase your strongest points and work on your weakest points. You have to develop your skills. You also have to show your dedication. Get to work on time and give 110 percent at every performance at every show. Just what you are doing is moving beyond yourself. I don’t look at talent as a gift from me. I look at talent as a vessel and a gift that comes through me.

YRB: You saw that firsthand when you watched Michael Jackson perform, right?

Chester: Absolutely. Michael Jackson was the reason, one of the main reasons, I decided to get into this business. It was his inspiration, not [only] as such a great artist, but such a humanitarian and understanding he is a regular human being. I’ve always had that mentality that when you step on stage, that’s when you display your super powers. When you’re off stage, there’s nothing more special about you than anybody else. When I met Michael that was exactly what I got from him. Getting to perform for him was a dream come true. When I got a chance to meet him and shook his hand and he looked directly in my eyes and said, ‘Great work,’ I was sitting there and shaking his hand and stuttering. He sat there and listened and was very, very humble and gracious. If the greatest entertainer of all time is that humble, what right does anyone else have to be arrogant?

YRB: When will you know you’ve achieved enough, that you can relax?

Chester: Never. Yes, I’ve had some success, but this, to me, is still the beginning. Knowing that I am using my art to help inspire people gives me the reason to continue. My stopping point is death.

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