In His Eyes: Chester Gregory


Some people may know him as the dashing young man that played the lead roles in “The Otis Reading Story” and “The Jackie Wilson Story.”  Others may know him as Terk from the broadway run of Tarzan or as James “Thunder” Early in his NAACP Award winning role in the broadway run and national tour of DREAMGIRLS. Currently starring as Eddie Souther, the male lead in the broadway run of “Sister Act,” his real name is Chester Gregery. He’s not only an actor, but a singer, songwriter, Apple tech geek and a businessman! Read more about him and his thoughts on natural hair here.


by Weusi

Q: Where are you from? Did you grow up around women that had perms or natural hair styles?
I’m from Gary, Indiana where the vast majority of women get their hair permed. But, it is also common for women to wear their natural hair. Also, I know a lot of women who don’t get their hair permed, but prefer to wear it straight.

Q: How did that influence your ideas of physical beauty?
My mother doesn’t have a perm, but she does have her hair straightened. Growing up in a predominately Black city, I just learned to appreciate the diversity of hairstyles.

Q: Who were some of the people/celebrities that you saw as beautiful growing up (natural, straightened or chemically relaxed hair)?
Halle Berry. The Jacksons were, of course, also from Gary, Indiana and had a vast range of hairstyles, each and every one of them. The hairstyles changed from year to year, which, looking back, indicates to me the decade in which we were living.

Q: Are there any character traits that you connect with a woman’s hairstyle?
I’m a sucker for a woman with big/curly hair. I notice that, not only do hairstyles change by the decade, they also change depending on what part of the country or even what city you’re from. But that part has been consistently sexy to me.

Q: Do you prefer permed or natural hair? Why?
I prefer a whatever hairstyle a woman seems most comfortable with. Hair is interchangeable, but if she finds a hairstyle that compliments her beauty, style, and grace, it’s icing on the cake.

Q: Are there any natural hair styles that you like the best?
Curly, wavy, big.

Q: When you are in a relationship, do you keep up with your women’s hair regimen? Do you know how often she washes her hair, conditions, colors, deep conditions, etc.?

Q: Do you keep track of what she uses on her hair? If you were walking down the beauty aisle would you know what to pick up for your lady?
Not at all.

Q: Have you ever dated a sister that has to wear “headgear” to bed? How do you deal with that? What’s your preference (bonnet, scarf, do rag, hat)?!
Yes. And, if she had to wear something to bed, then of course the bonnet or scarf.

Q: Have you ever been in a situation where you couldn’t put your toothbrush down because there were hair care and beauty products everywhere? If so, can you tell the story of how you dealt with it?
No, I haven’t.

Q: You have a wash and go. But I can imagine that, with the lights of a Broadway stage beaming on you 6 days a week, that can be damaging. I also know that you are a health conscious person and prefer to use natural products in your life. Are there any precautions that you take? What products do you use?
I wash my hair with Aveda Shampoo and I use Miss Jessie’s Curly Buttercream.

Q: As one of your friends, I know that you and your boys weren’t sitting around talking music, politics, theater and technology and someone suddenly said, “ Yo Chess … your hair is looking kinda dry. You should try ‘xyz.’ It worked wonders for me!” So, how did you learn about natural hair care?
My son’s mother told be about Miss Jessie’s Curly Buttercream. She tried it because she wears her hair natural and she recommended it for me. We both tried it and loved it. Once I discovered it, I haven’t found any other product that compares to it! If I’m having a day where my hair is dry and looking a mess, it’s only because I haven’t used Miss Jessie’s. It’s that serious.

Q: How do you feel about the state of brothers’ hair? I mean, we don’t do much with our hair. Should we be doing more?
Actually, out of all my friends, I’m the one who takes the least amount of care with my hair. Because my hair is naturally curly, I am automatically placed in the “pretty boy lane” and I try to resist that as much as possible! LOL! I get a haircut, on average, once a month. And when I do, I give the barber strict instructions not to line the front of my hair. Those super duper sharp edges ain’t me! A little water, Miss Jessie’s and a brush and I call it a day.

Q: You are a very fashion forward brother. Can you share some fashion “do’s and don’ts” for brothers that may be very comfortable in baggy jeans and t-shirts?
I actually don’t consider myself fashion forward at all. I pretty much just try to dress comfortably and neat. The only thing that bugs me is all these “Pants To The Ground.” Where’s General Larry Platt when you need him?

Q: Are there any sites or designers that you frequent or favor? Why are these special?
Of course I like Polo and classic casual wear. But, I also love a tee-shirt with a random design.

Q: We know that you can sing from your work on Broadway. You’re also getting a lot of attention on your musical projects. I saw one of your videos on VH1 Soul the other day. What’s up with you music career?
I’m excited to release a new project in the Spring and show growth musically. This is completely different from how folks may hear me every night on the Broadway stage.

Q: You seem to stay involved in a variety of projects. What do you have going on now?
Outside of performing in “Sister Act” on Broadway eight shows a week, I’m in the studio working on a new project and helping develop a new project for the theater as well. My other project is creative, but is outside of the performing arts. I’m a bit of an Apple enthusiast and have been for some time. I also like word games. They keep my mind sharp and keep my vocabulary from being stagnant. So … I’ve helped to develop a word game app call UnWord, which was recently approved and is available for iPhone and iPad users.

Q: Where can people check out your musical projects?
Join me at and follow me on Twitter at #ChesterGregory.


4 responses »

  1. Pingback: Sexy Curly Men We Can’t Take Our Eyes Off Of

  2. Pingback: ▷ Hombres rizados y atractivos de los que no nos podemos sacar los ojos | ❤️

  3. Pingback: Sexy Curly Men We Can’t Take Our Eyes Off Of - Naturally Curly

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s