Sam Singleton and Oscar Rivers didn’t expect to meet each other. Thankfully for them, school is one of the best places to make friends. Singleton, an accomplished genre-spanning singer, was starting his new gig as a substitute teacher at Simmons-Pinckney Middle School in September when he bumped into Rivers, a long-established and esteemed jazz instrumentalist, who was also subbing. The two struck up a conversation about Charleston and its music scene in the school lobby, and, upon realizing they had similar experiences in the music industry and life, forged a strong friendship.

Oscar Rivers is a familiar name to How Art Thou Jazz Lounge and Tapas Bar regulars and anyone who’s shown an interest in Charleston’s jazz scene over the past several decades. His group, Oscar Rivers Jazz, has gained local popularity for their jazz jams and musicianship, but Rivers’ career neither began nor peaked in the Lowcountry. After graduating from South Carolina State University, he obtained his master’s degree in music from Roosevelt University in Chicago. Being in such an important jazz hotspot like the Windy City in the ’60s and ’70s was the perfect place for Rivers to build an impressive resume (and autograph book). He’s played alongside many musical legends, including Quincy Jones, Etta James, B.B. King, Stevie Wonder, The Jackson 5, and The Temptations, just to name a few. “I think one of the greatest moments of my life is when I played with the Quincy Jones Orchestra and when I played with Sonny Stitt and Gene Ammons,” says Rivers. His most recent collaboration has been with his new friend, Sam Singleton.

Singleton was born in Charleston and raised in New Jersey. In his high school days he was part of a doo-wop group, and in his college years he was a singer for a funk band. After attending the University of Nebraska at Omaha, having kids, going to grad school at Central Michigan University, and completing a career in non-profit management, he retired to Charleston to be closer to his family. That was where his music career really began. “Music was always something I loved to do, but it wasn’t going to pay for [my kids] Chris and Kevin,” explains Singleton. But, with both sons out of the house, Singleton took the leap in 2006 and began performing, recording, and producing. His first album, Enchanting Songs of Love, was released that year.

After their chance meeting in Simmons-Pinckney Middle School, Rivers invited Singleton to sing with his band for a night and it turned into a regular live show, occurring on the second Sunday of each month. “He has been very supportive in relation to my musical presentation,” says Singleton.

“We’ve had three good runs on Sundays at the How Art Thou Jazz Lounge. It was just another beautiful comradeship with Sam and a mutual experience for the Oscar Rivers Jazz Trio,” says Rivers.

While Singleton is quick to point out that he sings many different styles including jazz, pop, soul, and the blues, he often brings an R&B vibe to his nights with Oscar Rivers Jazz. Both genres, as Singleton notes, have similar roots in gospel music. “I think the flavor is already there … The basis of all of it is found in the roots of this country.”

This month’s show will see the two musical veterans continuing their trend of stacking genres by adding holiday tunes to their repertoire. Classics like “White Christmas,” “I’ll Be Home For Christmas,” and “Have Yourself A Merry Little Christmas” will be performed in a jazz vernacular, alongside non-Christmas-referencing classics like “Mustang Sally” and “What’s Going On.”