Broadway star Chester Gregory: Michael Jackson is timeless

Chester Gregory
Chester Gregory Handout

Broadway’s Chester Gregory (Dreamgirls, Sister Act, Hairspray) is a triple threat: he’s got drive, energy and talent. The entertainer needs all of that and more to take on his lead role in The Eve of Jackie, playing 1950s-’60s pop/R&B star Jackie Wilson, aka Mr. Excitement, known for such hits as (Your Love Keeps Lifting Me) Higher and Higher, Doggin Around and Lonely Teardrops.

What can we can expect from the performance?

The Eve of Jackie is an intimate concert of Jackie Wilson in 1975 during the final leg of his national comeback tour. He has a scripted show, but he deviates from it and follows his instincts as he feels compelled to reveal the true nature of show business. What he doesn’t realize is that it is his final complete performance. The next day he collapses from a heart attack onstage and was never the same.

How personal is this to you?

Extremely. I’ve portrayed Jackie Wilson in several productions both on stage and in film [TV’s American Dreams]. I know what it’s like to make a lot of money and I know what it’s like to be broke. I know what it’s like to have people smile in your face and betray you. I know what it’s like to get the most devastating news of your life, then have to go out on stage and smile in front of an audience. All of these moments surface during The Eve of Jackie. It’s a multidimensional show that ultimately reveals the humanity behind the pop legend.

What do you want us to know about Jackie Wilson?

I want more people to be actively involved in celebrating his legacy as much as someone like Elvis Presley. In this day and age, it’s easy to watch footage of him and buy his music. I guarantee the more you learn about him, the more you’ll want to know.

How do you prepare for a role like this?

My preparation is incorporated into my lifestyle. I make sure I get plenty of rest and hydration. I have a vegan diet and I exercise regularly.

You are from Gary, Indiana — Michael Jackson’s hometown. The King of Pop was also said to be inspired by Jackie. To what do you attribute Jackson’s staying power?

Michael Jackson is classic. Timeless. Pure magic. Children have no bias. They will let you know immediately if they like something or not. When you play his music for kids, they instantly like it. This has already been happening for generations. That tells you something.

Who is on your iPod?

I have a playlist of several thousand songs. Everything is there from Frank Sinatra to Ella Fitzgerald; from (of course) Jackie Wilson to Kendrick Lamar; from Mozart to J Dilla.

What do you like to do when you’re in Miami?

Breathe! Miami’s tropical air is the best for singers.

The show goes through Sunday at the Carnival Studio inside the Arsht Center. Tickets: 305-949-6722,