Welcome to the first edition of Unsung Musicians, a series of articles that put a spotlight on those musicians that often have not received the acknowledgement they have earned throughout their career, having had meaningful contributions to music and an impact on the artists we know and love.
You can’t have a conversation about Jazz music without discussing Frank Sinatra, Billie Holiday, or Louie Armstrong. All superstars in their own right. However, there is another artist who took audiences by storm in his day.
Billy Stewart was born in Washington, D.C. in 1937. At the age of 12, he began singing with his younger brothers Frank, James, and Johnny. Collectively, they were known as The Four Stewart Brothers. As time went on and they become more familiar in the community, they were able to secure their own radio show at WUST-AM in Washington, D.C. The radio program would last five years.
Billy would eventually start making connections in the industry by way of filling in for local acts, further elevating his status in the community. He was discovered playing piano by Bo Diddley in Washington, D.C. in 1956 and Diddley would invite him to be one of his backup musicians. This would lead to his first big break, a recording contract with Bo Diddley’s label, Chess Records. The two struck up a friendship and Diddley would ultimately play guitar on Stewart’s track Billy’s Blues in 1956.
By the mid 50’s he secured a deal with Chess Records that lasted a few years before moving to Okeh Records. At Okeh, he would record Billy’s Heartache that featured backup vocals by the Marquees, a doo-wop group that featured none other than a young Marvin Gaye.
Stewart hit both the Pop and R&B charts big in 1965 with the songs I Do Love You and Sitting in the Park. He developed a unique style with his improvisational technique of doubling-up, scatting his words and trilling his lips.
Eventually, the desire to appeal to a broader audience came to be, and Stewart recorded the album Billy Stewart Teaches Old Standards New Tricks in 1966. The first single was his interpretation of the George Gershwin classic Summertime, which instantly became a top ten hit on both the Pop and R&B charts.
His music has been admired by the likes of Bob Dylan, referencing him, and playing his music often on his radio show, Theme Time Radio Happy Hour. Furthermore, he would go on to inspire one of the greatest musical minds and performers in history, Sir Elton John. John would write in his book, while speaking of music he collected as a child, “My favorite was Billy Stewart, an absolutely enormous guy from Washington, DC, signed to Chess Records. He was an amazing singer.”
Stewart died on January 17, 1970, in a car accident at just 32 years old. He died way too young, but his music lives on forever. Stewart was inducted into the Washington Area Music Association Hall of Fame in 2002. His music has also been featured in several films throughout the years, including Quentin Tarantino’s 2019 blockbuster Once Upon A Time In Hollywood. Several family members continue to pay tribute to him, performing his hits during their concerts and keeping his legacy alive.