With ‘Sister Act,’ Chester Gregory finally lets loose at the Broadway Theatre
Chester Gregory has remained a steady Broadway fixture since making his debut in 2003 in Hairspray. A replacement in the role of Seaweed, the Gary, Indiana native began a streak of supporting principal roles that included Terk in Tarzan, Dupree in Cry-Baby, Donkey in the Seattle tryout of Shrek The Musical, and James “Thunder” Early in the Dreamgirls national tour. Now Gregory is back on Broadway playing (Sweaty) Eddie Souther in Sister Act—the noble police officer who sends lounge singer Dolores (Patina Miller) to hide in a convent from her thug pursuers.
Gregory earned raves in 2000 when he starred in Chicago’s Black Ensemble Theater’s production of The Jackie Wilson Story. When the show toured in New York at the Apollo Theater, Hairspray creators Marc Shaiman and Scott Wittman were taken by Gregory’s energetic performance and immediately cast him as Seaweed in their hit musical. Since making his Broadway debut, Gregory has earned an adoring fanbase, but his stage journey has had notable low points. Tarzan opened to terrible reviews, Cry-Baby only lasted 68 performances, and the industry buzzed when Gregory was not cast as Donkey in Shrek’s Broadway transfer, after creating the role in Seattle.
Despite these potential setbacks, Gregory plunged forward, giving a well-reviewed performance in the national tour of Dreamgirls and creating a slick R&B/soul solo career. Gregory sat down with Stage Rush in his dressing room at the Broadway Theatre (coincidentally, where the musical about the ogre played) to discuss Sister Act, his history with the Apollo, and what happened with Shrek.
How did Sister Act come into your life?
Sister Act came into my life by way of my son’s mother, Kimberly Herbert Gregory, who is an actress as well [last seen in By The Way, Meet Vera Stark]. She saw the production in London and recommended I audition for it.
You were originally considered for the role of Curtis, the villain. Does it take major cajones to request another role, or do you find it accepted?
I’ve become a big fan of following my instincts in the past couple years. It just didn’t feel right. I feel better if I go in for a role that I feel really comfortable with, rather than trying to do something that doesn’t fit. I’m glad they were receptive to that, because a lot of times people aren’t.
Your character Eddie Souther is the one from the movie that gets a completely new characterization in the musical. Was it freeing to not have to live up to the movie portrayal and make it your own?
Definitely. Just following the direction of Jerry Zaks, whom I trust with all my heart and soul—he was great to work with. We just stripped it down to a really simple idea of him being “Sweaty Eddie” in high school, and it sort of resurfaces when Dolores comes around. It was a lot of fun to just take that real basic idea and add nuances with each performance.
How did you feel about the idea of Sister Act?
I was excited about it. Right when the Dreamgirls tour ended, two weeks later I was in rehearsals for the reading. It was just perfect timing. I heard the show was great. I was excited to be involved in a project with Whoopi Goldberg [who produces]. Plus, getting a chance to work with Patina Miller. We were this close to working together in Dreamgirls. Now I get a chance to spend time with and play opposite somebody I’ve heard about for so long.
VIDEO: Chester Gregory on his solo number, “I Could Be That Guy,” from Sister Act, and onstage mishaps
It will always remain as a big surprise to me that you didn’t continue with the Broadway transfer of Shrek, after playing the role of Donkey in out-of-town tryouts in Seattle. What did that time in your life feel like to you?
For me, it was a situation that ultimately, it was what it was. It wasn’t just me. There was a story about me and the dragon. But there was other stuff going on. Even if you look at the show now, they still revise who was involved with it and all that stuff. The unfortunate part of it was there was this big story about Kecia [Lewis-Evans, who played Dragon] and a little sentence about me. [Editor’s note: Reports from publications, such as Variety, stated that Gregory was dismissed due to negative reviews, and Lewis-Evans, due to the role being dramatically reworked for the Broadway run.] You know how stories are; they’re stories. The situation for me was a growing experience and I got a chance to experience another side of the business, and the situation ultimately worked out to my benefit. Four weeks later, I booked Dreamgirls. I had a year off with pay. I had a chance to get over the initial shock of my ego and throw all that aside and really enjoy life that year. It was a learning experience and I’m a better person because of it.
What does the Apollo Theater mean to you? It has such music history, but it also plays a part in your history? The Jackie Wilson Show played there and so did the Dreamgirls tour.
The Apollo is everything to me. So many icons have performed on that stage. The Apollo is my New York debut, coming from Chicago with The Jackie Wilson Story. We went on tour and our first stop in New York was the Apollo Theater. Right after the Apollo was my Broadway debut [in Hairspray]. So the Apollo is a very special place to me. Even when I go there now, it’s like seeing old family members. It’s a historic venue. I’m honored to be a part of its history.
Is it correct that you’ll be leaving Sister Act to do The Jackie Wilson Story again when Chicago’s Black Ensemble Theater opens its new venue in November?
[Gregory hesitates with a long pause, interspersed with nervous laughter.] We’ll see. We’ll see. [Editor’s note: The Chicago Sun-Times published an article, reporting that Black Ensemble Theater artistic director Jackie Taylor intends to star Gregory in a reprisal production of The Jackie Wilson Story when construction on the company’s new venue is completed.]
How long is your contract with Sister Act?
I’m signed for a year.
Regardless, your performance in the title role in The Jackie Wilson Story back in 2000 got you fantastic notices from the critics and launched your career.
I’m very proud of the Black Ensemble Theater. Jackie Taylor, the founder and artistic director, is gearing up to celebrate their 35th anniversary. They’re launching a new building in Chicago. It’s a new space with two theaters inside of it. It’s a very big deal. The first show they’d like to do is The Jackie Wilson Story to debut the space. Now, of course when dealing with construction and all that stuff, you never really know. We’ll see what happens when the time comes.
Do you feel a power struggle between your solo music and your stage career, or do you see them coexisting?
I see them coexisting now. In the past, I definitely struggled with playing one against the other and having two careers. It’s been my goal this year to work everything into one universal idea, with me doing Broadway shows and also doing music that’s appealing to both audiences. That’s what I’m going for.
What do you think of Chester Gregory’s story, Rushers? What has been your favorite role of his? Do you still find it surprising that he wasn’t cast in Shrek on Broadway? Would you like to see him carry The Jackie Wilson Story to New York? Leave your thoughts in the comments below, and tune into this week’s Stage Rush TV for more of my interview with Gregory!