Growing up in Awendaw and attending schools in Mt. Pleasant, Charlton Singleton was an aspiring pianist as a youngster. He started taking lessons at the age of three and played regularly before picking up the violin in grade school. He never seriously considered learning jazz or the trumpet until he caught Dizzy Gillespie in concert.

“When I was in the sixth or seventh grade, Dizzy came to town and played at the Gaillard Auditorium,” remembers Singleton, who is currently the artistic director and conductor of the Charleston Jazz Orchestra. “I’d heard of him, of course, but I really wasn’t much into the trumpet back then. The piano was my main instrument. My father took me to the concert. I remember him playing this one particular song called ‘Birk’s Works.’ His mute sounded really nice. I was very inspired.”

And Gillespie wasn’t the only jazz cat who inspired Singleton that night. “[Saxophonist] Lonnie Hamilton, one of the jazz hierarchy in Charleston, was the opening act that night, and he really impressed me, too. I didn’t really know what I was watching, but I liked it,” he says.

As fate would have it, Singleton’s parents were close friends with Lonnie Hamilton, the man who opened for Gillespie that night, as well as other Lowcountry jazz artists. During Singleton’s high school years, his folks encouraged him to catch Hamilton and his band, the Diplomats, at Henry’s House and other local jazz venues.

Singleton switched gears and put his efforts into learning the horn while attending Laing Middle and Wando High schools, landing the top chair in the all-county and all-state middle school and high school bands.

“Like anything that you do, if you want to be good at it, you absolutely have to practice,” says Singleton, who still maintains a disciplined daily practice regimen. “Like, if I wanted to be a musician in an orchestra, I know I’d have to know all my rudimentary things, my scales, arpeggios, and a certain repertoire — and that’s even before I get the job. It’s all practice, and that goes for any profession. If you want to be noticed and admired, you have to work at your craft.”

After a stint at the Berklee College of Music in Boston, he dove into the marching band and ensemble work at S.C. State University and earned his degree in music in 1994.

Through the late 1990s and 2000s, Singleton performed music almost as often as he taught it to students. Back then, he was just as comfortable in jeans and a T-shirt with ska-funkers Skwzbxx or funk cover band Plane Jane on stage at a local watering hole as he is now in front of a sold-out crowd in a theater clad in full tuxedo and tails.

“Being a student of music who likes all types of music, take it all in. I make myself available,” Singleton says. “That’s the key to versatility and entertaining. I think being versatile and prepared for any type of musical situation that you’re put into is like being a versatile actor who can play any part. I want to be that type of musician.”

As the leader of the Charleston Jazz Orchestra and the vice president of Jazz Artists of Charleston, he’s literally the poster boy for local jazz (see any JAC flyer from their last two seasons, including the handbill this week’s show with Quiana Parler).

And whether they’re delivering a swingin’ set of classic Count Basie, Duke Ellington, or Dizzy Gillespie tunes or an exotic set of Latin-themed or cinematic numbers, the CJO performances at the Charleston Music Hall are consistently powerful and entertaining.

“Part of making those shows work is in engaging your audience,” says Singleton. “The more you engage the audience, the better they can relate, share, and be a part of the experience. They can laugh and clap and have some sort of connection to the music.”

And Singleton should know. After all, a live performance by Dizzy Gillespie changed his life forever.