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Dean St. Hillaire: Reggae, calypso, and jazz musician

By Carolyn Males + Photos by Mike Ritterbeck

As we sit at a café on Skull Creek, Dean St. Hillaire is tapping out a reggae rhythm on the tabletop. For the last hour he’s been giving me a lesson in reggae, calypso and all their variations. Our waterside view is a fitting setting for these tropical beats. Normally he’d be on the deck of a Hilton Head resort, singing and strumming classics like Bob Marley’s “Stir It Up” or newer tunes like “Roller Skates,” making his listeners feel as if they’re sitting on the edge of the Caribbean on a coconut tree-lined beach.

But when he starts talking about playing jazz on his sax and his weekly gigs at the Jazz Corner’s Fat Tuesdays, the beat changes. And I’m transported back to Bourbon Street in New Orleans where music breaks out at every corner.

Like many creative folks, St. Hillaire has another profession as well. In fact, he had just come in from Sevierville, Tennessee, in the foothills of the Great Smokey Mountains where a boom in cabin sales has fueled his real estate career. However, his heart –– family and music –– are based here in the Lowcountry where he lives with his wife, Robin, and their two children, Kenneth and Deana.

[LOCAL Life] Grenada, where you grew up, has such a rich culture of music, especially calypso and its more upbeat, energetic cousin, soca. I imagine your life was infused with this sound.

[Dean St. Hillaire] We went to a small village church where, by age six, I was singing with my mom and her friends at Sunday services. We had tambourines but that was all. One day I told my friend, Reuben, “I’m going to play guitar in church.” He said, “Well, first you’ve got to have a guitar.” [St. Hillaire laughs.] It was intuition. I kind of knew in my head that once I got an instrument, I was going to play. I felt I had to do this.

When I was about thirteen, a friend gave me my first guitar. Then my godmother bought me a better one. We had no television so I had to do something, and I taught myself to play. Then I brought my guitar to church and began playing. Soon I got other friends with guitars to come, so I switched to a bass that the church bought me. More kids joined us, including a piano player. So that’s how we developed the Praise Team.

[LL] Tell me a little about the different kinds of Caribbean music you play.

[DSH] Calypso has different genres just like R&B has soul and funk. Classic calypso like “Day-O” are like folk songs. Social commentary calypso is slower, it’s educational and alerts you to something. [To illustrate he sings out Mighty Sparrow’s “Education A Must” which speaks of its importance to a rising population.] Soca, on the other hand, is fun dance party music. Sometimes there’s a bleeding over of both genres where a funny song can have a social education format. Calypso is always changing. I go back home and think I’m hip, and the young kids say, “Oh, Dean. We don’t do that anymore.”

There’s also parang, which has its roots in Trinidad and is played around Christmas. It celebrates not just the birth of Christ but Caribbean foods. [Here he starts beating out quarter notes divided into triplets.] You’ve heard parang, but you just don’t know it. [He starts singing “America” from West Side Story as he taps the beat.]

[LL] And reggae?

[DSH] Reggae, too, has changed. First you had roots reggae like Bob Marley’s “Stir It Up,” then later you have Yellowman doing dance hall reggae that makes you want to move and party. And there’s ragamuffin, with its harder more aggressive sound where guys growl. It’s in-your-face, like serious rappers.

[LL] You’re also a jazz musician.

[DSH] I’d always been interested in jazz. When I was growing up, Wednesday was jazz night on the radio station. I would stay up until midnight, listening to the old greats like Count Basie and Charlie Parker. Then when I was seventeen, a Peace Corps worker from Indiana came to our school. He was a science teacher, but he’d been a music major in college. Whenever I walked past his house, I’d hear this beautiful piano playing –– classical and jazz pieces like Duke Ellington and Cole Porter.

One day I opened the gate, went in and asked, “Can I come listen?” He said, “Sure.” So I went in, and he started teaching me music theory and how to play the piano.

[LL] So you played guitar, bass and now piano. How did you get to the sax?

[DSH] I used to have this recurring dream. I’d get up in the morning and tell my mom, “Hey, I had a dream,” and she’d say, “I know. You had a dream about playing the saxophone again.” Then one day I was at the teacher’s house and saw a box. “What’s this?” I asked. “Oh, that’s my saxophone,” he told me. When my face lit up, he said, “Do you want to play?” He took it out and from then on my piano lessons changed to saxophone lessons. Eventually my aunt gave me money to buy a saxophone, but they’re expensive in Grenada so I bought a Bundy, which was school grade. After I paid off my monthly balance, I thought “this sounds terrible.” Then my teacher said, “I don’t play anymore so you can have mine. My students can practice on yours.” His was a Vito, and it sounded amazingly good.

After high school I went straight into the military band and played saxophone there for two and a half years. Then one of my friends, who’d been in the band and now was working on a cruise ship, offered me a job. So for four years, I sailed around the Caribbean, the East and West U.S. Coasts and Bermuda, singing and playing reggae on bass guitar. It was fun but it got monotonous. I needed more.

[LL] How did you end up in Hilton Head?

[DSH] I had friends who had moved down here and told me, “You’ll like it.” I met my wife, Robin, and started gigs for Marriott, SERG and private jobs. I worked mostly solo, but I also played gigs with bass player Bobby Paschal and guitarist Craig Washington. Growing up in Grenada, I’d dabbled in steel drums, but when I came up here I realized people really loved the sound, so I decided to get into it a little more. Right now I’m raising money to start a steel drum orchestra in my old Grenada neighborhood so that young people there have an opportunity for a career in music like I’ve had.

[LL] So what is your repertoire?

[DSH] A mix. I play anything I hear that sounds good — reggae, jazz, calypso, Jimmy Buffett, James Taylor, Kenny Chesney, Norah Jones… whatever I gravitate to, I play. As long as it’s good music and it makes you feel good. LL


Good difficulties

The flight attendant announces over the intercom over the Atlantic, speaks difficultly of difficulty, technical in nature. She continues to announce apologies and keep seat buckles fastened

I search for bursts on the wing

The attendant’s measured voice regrets to inform the feature film will be twenty minutes delayed. Those watching won’t see the finale before the plane lands in fifteen

I burst out laughing

— Delia Corrigan

Tidal Flats by Cindy Chiapetta

Have a special artistic talent? Step into LOCAL Life’s and the Hilton Head Island Office of Cultural Affairs’ monthly Creative Conversations spotlight. Go to to apply.