Broadway Star Chester Gregory Speaks On ‘Sister Act’ Musical, Meeting Whoopi Goldberg + Drops New Mixtape ‘If U Only’

Chester Gregory is a refreshing new voice to the neo-soul generation. You may not know who he is musically, but as a hardworking thespian he recently starred in the Broadway musical Dreamgirls and is currently rehearsing for his role in Whoopi Goldberg’s theatre production of Sister Act. Last week we talked to the Gary, Indiana native about being on such an epic project and dropping his soulful music effort, If U Only… The Mixtape, on Valentine’s Day. -Niki McGloster

Tell me how you got on board with the Sister Act musical?
Well, while we were on the last leg of the tour, I had an opportunity to fly back to New York for a little bit. I heard about Sister Act coming and my agent called me in. They actually had seen me [playing] as Curtis, the mean boyfriend of Delores, but I asked them if I could come in for Eddie instead, the good guy cop who she falls for in the end. I went in to audition like four times, and after the fourth audition, they called me and extended the offer. It was right on time. I’m really thankful. The past eight years in New York that I’ve lived here, I’ve pretty much gone from job to job and Broadway show to Broadway show and I’m thankful.

That’s dope. What’s your relationship with Whoopi?
I don’t know her well personally but we do know each other. She had seen me a couple years back at a dinner for the mayor where I was invited to sing. I wasn’t sure who was there because it’s a really private event at his house, and I didn’t get to see anybody. When I walked upstairs and got ready to sing the song, there was Whoopi Goldberg sitting there. So, I sang and made sure that I went up to her and talked to her. We’d also met one time before when she was on Broadway; Whoopi was doing Ma Rainey’s Black Bottom. Then, at my third audition [for Sister Act] she was there. I walked in and didn’t expect her to remember me, but she did [laughs]. That meant a lot to me.

It’s good that she’s familiar with you. I mean, you know Whoopi. Only great things can come from that [laughs]. Now, how do you feel about the cast?
I must say, this is one of the most talented casts I’ve ever worked with. Everybody is amazing. 

Is there anyone you’re excited to work with?
Yeah, I’m excited to work with Patina Miller. We did the reading together and she was amazing. She and I clicked immediately when we met each other, and she was almost going to do Dreamgirls, so I’ve heard her name for the past two years. Now I’m finally getting the chance to meet her and work with her.

Cool. Now, I want to transition into talking about your music career a bit. Have you always wanting to sing?
Acting, singing and performing is all one category to me instead of three separate categories. It’s just what I’ve always to do since I was in elementary school, so I really admired performers who have had multiple genres happening in there career. Michael Jackson, Sammie Davis Jr., Gregory Hines and people who act and perform and have music going on all at the same time. It’s all I’ve ever wanted to do.

I haven’t gotten a chance to see you perform, but just from reviews I can tell you’re very talented. Plus, I heard your track “If U Only” and I can hear a very soulful sound. Is that the direction of your music?
I think I will always identify myself as being a soul singer, and by “soul” I don’t necessarily mean a certain genre, I just mean that there’s passion and experience behind what I’m singing about. First and foremost, I’m conveying the message of the song before it’s a vocal performance. I want people to feel what I felt when I wrote it or when I’m singing live. But as an artist, I want to have songs that have crossover appeal. It’s sort of like the rawness of the Stax recordings like Otis Redding, Carla Thomas, Isaac Hayes and those people. They would identify themselves as soul singers, but yet, they would be on the pop charts and the R&B charts.

Where did the inspiration come from for the acoustic version of the “If U Only” track?
Well there are a couple of people that come into play. Ledisi has become a great friend of mine but also someone who supports my music career and she heard my first album and told me how much she loved it. She saw me sing live a couple of times and she would always tell me, ‘You should do something with a guitar,’ so that was always in the back of my mind. Michael A. Cherry directed a short film called This Time, and he was looking for a song to feature in the film. When he described what he needed the song to say, I sent him “If U Only,” the original version from the album. So, he heard that and he loved the song, but said, ‘Do you have a version of the song where there’s just maybe some guitar?’ There the guitar thing was again and so I went to the studio, sang the vocals over, added some guitar and had the new version by the time we shot the video.

What can fans expect from the mixtape as a whole?
The mixtape itself will be one long continuous track of music. With this mixtape I want to go back to the original idea of the mixtape. DJ Mr. Mo is really going to cut and scratch in not only my vocals but vocals for the original songs or inspirations for the song. You just see an evolution of how music has evolved but yet how these things are universal.

Why did you choose Valentine’s Day to release this ‘tape?
With “If U Only” being a romantic song about expressing how much I love someone, you think about how much you appreciate that somebody. And with Valentine’s Day being about love and all that, there’s a nice acoustic version of the song and I thought it’s be nice to tie it all in. 

Well since this all came out on the “lovers’ holiday,” I have to ask… are you dating?
No, I’m just chillin’ [laughs].

Download the mixtape exclusively here.