Spicing up Monk Charleston Jazz Orchestra to Latin-ize the music of Thelonious Monk

Jazz pianist Thelonious Monk performs at the Newport Jazz Festival in Newport, Rhode Island, in 1963.

As the musical director and conductor of the Charleston Jazz Orchestra, trumpeter and vocalist Charlton Singleton values the opportunity to tinker with classic jazz standards and put new twists on the great songs and compositions of the jazz world. Working with his jazz orchestra colleagues, many of whom create their own arrangements for the band, Singleton digs up cool deep cuts, experiments with musical structures and restyles various formats every season.

This Saturday, Singleton and the Charleston Jazz Orchestra (CJO) will present a special rendition of Latin Night, one of their most popular annual themed events, at the Charleston Music Hall under the billing of “Monk, No Chaser: The Latin Side of Thelonious Monk.”

Presented by the independent musical nonprofit the 19-piece Jazz Artists of Charleston (JAC) as part of the CJO’s seventh season, the Holy City’s veteran big band will perform two individual sets of well-loved and somewhat obscure pieces by innovative bebop pianist and composer Thelonious Monk.

According to Singleton, the CJO will spice things up with an extra Latin rhythms and melodic reinterpretations of Monk’s music: from salsa, rumba and bossa nova to Afro-Cuban styles and beats.

“When we come to this year’s Latin Night program,” Singleton says, “we knew that we’d already done a Cuban-themed show, and a Brazilian-styled show with the music of Jobim, and we’d brought in a Calypso/Caribbean style. I thought of trying some Thelonious Monk.”

The CJO regularly celebrates the works of featured jazz composers with thematic programs from season to season, including material by the likes of Herbie Hancock, John Coltrane, Horace Silver, Billy Strayhorn and many others. Tackling the vibrant and challenging music of Monk seems to fit the pattern nicely.

Born in North Carolina and raised in New York City, the late Thelonious Monk was an eccentric composer, pianist, and bandleader with an unorthodox approach to technique and a penchant for advanced rhythms, strange harmonies and occasionally joyful dissonance.

During his heyday in the 1940s, ’50s and early ’60s, a period in which he collaborated with or played alongside such jazz champs as Dizzy Gillespie, Charlie Christian, Kenny Clarke, Charlie Parker, Clark Terry, Miles Davis, and Art Blakey, Monk was somewhat misunderstood and undervalued in the jazz world, but music critics and jazz fans eventually came to admire and revere Monk’s unique genius over the years.

“Some people don’t realize that next to Duke Ellington, Thelonious Monk is the most recorded jazz composer ever,” Singleton says. “And he really doesn’t have a whole lot of songs compared to many other composers. Monk has a great catalog of hits, popular standards that are so dynamic and recognizable.”

“There aren’t many arrangements for Monk material in a Latin style out there, so that gives us the opportunity to showcase the arranging skills of locals here in the jazz community,” Singleton adds.

Both performances on Saturday will feature newly penned arrangements by a handful of CJO members, including saxophonist/woodwind players Jack Pettit (“’Round Midnight”), Robert Lewis (“Ruby, My Dear,” “Criss Cross”), Jon Phillips (“In Walked Bud”) and Mark Sterbank (“Evidence,” “Ask Me Now”), among others. Singleton himself will conduct his own reworking of Monk’s highly popular “Straight, No Chaser.”

“The loyal CJO followers and season ticket-holders in our audience really get it and understand the significance of an arrangement of a song,” Singleton says. “How often do you hear ‘Straight, No Chaser’ played in a Latin style?”

The roster of CJO musicians for the shows will include Singleton on trumpet and conducting in front of a horn section comprised of trumpeters Chuck Dalton, Stephan Berry, Dan Bellack and Kevin Hackler and a trombone line of Phil King, Ken Foberg, Jay Jehl, and Stephen Spaulding. The woodwind section will be situated up front with Robert Lewis, Jon Phillips, Mark Sterbank, Jack Pettit and John Cobb handling saxophones and flutes.

The orchestra’s rhythm section will feature electric guitarist Tyler Ross, upright bassist Jeremy Wolf, drummer Ron Wiltrout, percussionist Gino Castillo and pianist Gerald Gregory.

Much of the spotlight will certainly aim at Gregory as he handles the keys during Saturday’s event. Fortunately, Singleton and the CJO have plenty of confidence in the pianist’s skill and musical instinct.

“Gerald is probably one of the most creative musicians I’ve ever watched and performed live with,” Singleton says. “He’s one of the best pianists in Charleston, between his solo work, duo work, trio work and ensemble work. He’s the guy everyone wants on their gig.”

Though he’ll be in the spotlight, Gregory says he isn’t feeling the heat.

“I don’t feel a lot of pressure,” Gregory says. “I trust musicians in this band, and they make me play better. At the same time, I am conscious of the fact that I’m no Thelonious Monk, but I’m not trying to be. I would just like to honor his music the best I can.”

“I wish I had more time to practice,” he laughs.

Over the last 10 years, since graduating from the College of Charleston with a bachelor’s degree in jazz performance and composition, Gregory has been performing professionally in a wide variety of musical settings around the local scene and up and down the East Coast.

He’s been a core member of the Charleston Jazz Orchestra’s rhythm section from the ensemble’s earliest days in 2008, and he currently jams, composes and performs with the Charleston Latin Jazz Collective and several experimental combos and projects ranging from traditional jazz to funk, rock and Brazilian-based styles.

“Monk was one of the first pianists I checked out,” Gregory says. “I started listening to him around 11 or 12. I had been listening to Erroll Garner, Oscar Peterson and others of that era on cassette tapes that my mom had prior, so hearing Monk was a revelation. His approach, harmony, and rhythmic differences were very apparent to me, but I had no idea why. I wasn’t informed enough musically to understand but I knew I loved it.”

While most of Monk’s recordings featured him at the piano with the backing of small combos, Gregory doesn’t expect it to be too tricky or difficult to render some of the tunes as a full-sized big band on Saturday.

“I think because Monk’s harmonies were specific, and, in some cases, big and lush, it was not too hard interpreting his music for a big band,” Gregory says. “There’s an album called ‘Monk Big Band and Quartet’ recorded at the Lincoln Center, so this is not the first time it’s been done.”

“We have a lot of great talent in the CJO, as far as arrangers for the band,” Gregory adds. “I heard the music come alive for the first time last weekend. There are a lot great charts. There didn’t seem to be a lot of difficulty ‘Latin-izing’ these tunes from an arrangement standpoint. The melodies are so strong, they seem to work well with any groove you put behind them.”

It will be exciting to hear how Gregory and his bandmates rework and celebrate selections from the Monk repertoire on Saturday. From his soft ballads to his high-tempo workouts, Monk had a very distinctive style. Revamping some of those key songs with a new sense of Latin elegance is a feat Singleton and the CJO look forward to achieving.

“It’s all about the presentation of the music,” Singleton says. “We have talented musicians who are world-class on their instruments, so the band can handle even the most creative and challenging arrangements in the set. We’ve been so fortunate to be able to pull off some crazy ideas, and we’re very lucky that our audience really trusts us.”