1937 - 1970
March 24, 1937-January 17, 1970
William Larry Stewart II was born and raised in Washington, D.C. Known by his stage name Billy Stewart, he was a talent far beyond most R&B singers of the 1960's, having a signature sound, which no one could imitate. His rolling tongue, scatting, and vibrato gave a uniqueness to his songs.
Billy Stewart began singing with his brothers, Johnny and James Stewart, and cousin, Norman Smith, in a gospel group, The Stewart Family, in the 1950's. His mother, Emma Stewart, taught Billy how to play the piano at an early age. He went to Armstrong High School in DC, where he began singing the hit tunes of the Doo-Wop era. Early in Stewart’s singing career, he sat in for Ronald “Poozie” Miles of the DC Doo-Wop group, The Rainbows, during a performance at the Royal Theater in Baltimore.
Stewart's passion for singing in his early years made him a DC legend as he sang in many DC area nightclubs from U Street to the local favorite The Shelter Room in Northeast, Washington, DC. Stewart was known to break out singing on the sidewalks of DC. He was a favorite at the Howard Theater in DC, The Apollo Theater in New York, and other concert theaters along the "Chitlin' Circuit".
Stewart was noticed by legendary rock and roll guitarist Bo Diddley when he lived in DC, which led to him backing Diddley as a pianist and touring with Diddley’s band for several years. Not only was Bo Diddley a legendary recording artist for Chess Records in Chicago, but he was also an A&R man for the label scouting for R&B talent to bring to the record company. In 1956, Billy’s first songs were for Chess Records in Chicago, where he recorded “Billy’s Blues (Parts 1 and 2), and for Okeh Records in New York where he recorded “Billy’s Heartache”.
In the early 1960's, Billy Stewart returned to Chess Records and recorded his charted tune “Reap What You Sow” with his cousin Grace Ruffin’s group The Four Jewels singing background. His charted songs at Chess Records - such as "I Do Love You", "Sitting in The Park", "Reap What You Sow", "Fat Boy", “Cross My Heart”, and stunning remakes of George Gershwin compositions, "Summertime" and “Secret Love” - made him a national singing sensation.
During his life, Billy Stewart battled health problems including issues with his weight, but it never stopped him from giving all he had on stage. That came to an abrupt halt, however, when Stewart tragically died on January 17, 1970, after his car plunged into the Neuse River in Smithfield, North Carolina. He and his band were in route to a performance in Columbia, South Carolina. Stewart, along with three of his band members riding in his car, were killed as the vehicle sank into the river. The remaining band members were driving in a separate car, which was not involved in the accident.
In 2020, a documentary film, “Fat Boy: The Billy Stewart Story”, was produced and directed by Emmy Award-winning documentary filmmaker, Beverly Lindsay-Johnson, of Kendall Productions, LLC. The long-awaited documentary has been broadcast on at least 102 PBS stations nationwide. In 2021, the "Fat Boy" documentary won the "Communicator Award" for Excellence in the Television Documentary category.
“Yes, I'm sitting right here waiting for you my dear, wondering if you ever want to show up "
- Sitting in the Park