With just as much passion as you would find in any of his many stage performances, Chester Gregory joined me on a call to share a little bit about his life and career. A native of Gary, Indiana, Chester is a multi-award-winning performer who most noticeably captivated audiences as the troubled yet talented Jimmy Early in the Broadway production of Dream Girls. Appearing nationally and internationally in plays ranging from The Jackie Wilson Story to Hair Spray, he’s also managed to release his debut mixtape titled In Search of High Love. Now, just in time for Valentine’s Day, Gregory released the video for his If U Only mixtape and single. Here’s our Chester Gregory interview.
Parlé Magazine: Chester how are you? I’m glad you could spare a moment for this Chester Gregory interview, between acting and recording your If U Only mixtape, you must be really busy.
Chester Gregory: I’m great, well we’ve just finished up Dream Girls, which was an amazing time, as you know I played Jimmy Early and we went through about 30 cities and now I’m in rehearsal for my next role which I am very excited about.
Parlé: I’ve read that you’ve won an award for your work as Jimmy Early, similar to Eddie Murphy being nominated for playing the same role in the film adaptation of Dream Girls, have there been any comparisons between the two of you?
Chester: It’s actually kind of a funny thing you asked that. I’ve sort of had a link to Eddie Murphy during my career not only did we share Jimmy Early in Dream Girls but the character I will play in my next show is named Eddie as well as I was cast as Donkey in Shrek, a role that he originated. I have had the chance to meet him while on tour in L.A. and he’s a great person and while people do make comparisons I try to bring the best performance to serve the story in my own way.
Parlé: You mentioned your new role, can you share a little more about that for this Chester Gregory interview?
Chester: Well my character’s name is Eddie and I play a good guy cop in Whoopi Goldberg’s production of Sister Act. He helps out the main character Delores much like the movie version.
Parlé: That was definitely a favorite of mine growing up, I imagine it will be a lot of fun.
Chester: It’s amazing so far, we are rehearsing a lot now getting things together.
Parlé: You were also in another favorite childhood movie of mine by the name of Tarzan, one of several soundtracks you’ve loaned your vocals to. Now on the verge of having two albums under your belt and the If U Only mixtape on the way, is it safe to say in this Chester Gregory interview that you’re very passionate about your singing as well?
Chester: It’s kind of all in one to me. I’ve never wanted to just be a singer or dancer or actor, I’ve always wanted to do them all, ever since I was a little boy I loved to do everything. It’s a package.
Parlé: A career in performing theater, such as being Jimmy Early in Dream Girls, isn’t an easy one to master, how did you start out on your journey and what led you to where you are now?
Chester: My mom was an elementary school teacher and she would ask me to help out with her productions and people noticed little things I was good at and she encouraged me and supported me when I chose a career as an entertainer. I went on to audition for art schools and after three times I finally got in and studied for years and years taking every advantage I could. I auditioned for plays and talent shows and continually practiced. I knew that I wanted to make sure that my passion matched my skill.
Parlé: And skilled you are, listening to some of your music from previous performances as well as your first album I couldn’t help but get a very neo-soul feeling from your personal music. Can you share in this Chester Gregory interview if there’s a direct influence for that?
Chester: It’s kind of a mix of things and feelings. I’ve covered a lot of songs in the past that required different styles and that kind of bleeds into how this project is. I tried different songs and sounds and for each song there was a different sound so I will sing in the voice that the song feels like. For my single “If U Only,” it was originally sung sans the guitar until a good friend of mine, a singer by the name of Ledisi mentioned an acoustic version and I decided to try that which led to the current production of the single.
Parlé: If U Only mixtape is scheduled to release this Valentine’s Day, what can fans and Chester Gregory interview readers expect to get from you that they would normally not see on stage?
Chester: They will be able to get more of an infusion of my personal life. Acting allows me to share someone else’s story with the audience whereas my music allows me to share my story and get people to relate to me.
Parlé: And I understand you have a video as well for the If U Only mixtape?
Chester: Yes, I’m very excited about it. We finished shooting in L.A. about a month ago and I just saw the final clips which were great. It was a good experience. It really conveys the message of the song and prepares you for the rest of the album. The director was great as well, I actually had to shoot a chorus backwards so that it could be played a certain way so I believe it will definitely entertain.
Parlé: Would you ever consider a career as just a recording artist?
Chester: You know, I’m fortunate enough to be doing both acting and singing right now and they allow me to share my life and my experience and allow others to relate. I’m very excited about sharing my reality in music but still love performing and being able to bring a story to life.
Parlé: Having won several awards, traveled the world, and produced two albums, what would you say was the best moment of your career?
Chester: The best is yet to come, I try and enjoy every moment of it and I’m thankful for the opportunities I have so every moment has been a great moment.
Parlé: And if you had a motto or a saying that helped you get to this point in your life what would that be?
Chester: The sooner you discover what your personal legend is, the sooner you’ll follow your heart, mind, and soul. Growing up not everyone told me I was good, that I could act or sing and if I listened to those people I would have allowed them to destroy my dream. So I had to follow my heart because I knew this is what I wanted.
Parlé: On top of your much-deserved success I wish you more success and thank you for speaking with us for this Chester Gregory interview. Good luck in your new role!
Chester Gregory interview image credit: Instagram
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