Billy Stewart was born William Larry Stewart II in 1937 in Washington DC. He was the eldest of four brothers who sang Gospel together as the Four Stewart Brothers, starting when Billy was just twelve years old and the other brothers younger still! The group were good enough to get their own show on local radio station WUST.
Occasionally Billy was asked to sit in for the Rainbows, a group that Don Covay had set up locally. He also learned to play piano, performing locally. These opportunities brought him to the attention of Blues singer Bo Diddley, who took him to Chess Records in 1955, where he recorded one instrumental single, “Billy’s Blues Pt 1”, released in 1965, with Bo Diddley playing guitar. Stewart sings on part two on the B-side.
The following year saw Stewart recording “Billy’s Heartache” at OKeh Records, a song co-written Stewart and Ellas McDaniel, otherwise known as Bo Diddley. Backing vocals on the song were provided by the Marquees, featuring a young Marvin Gaye!
In 1962, he returned to Chess to work with Billy Davis, releasing a string of twenty-two singles between 1962 and 1969. Having started out singing and playing Blues, Stewart moved into Soul and R&B, achieving chart success with several of his songs, including “Fat Boy”/ “Reap What You Sow” (number eighteen R&B and number seventy-nine Pop), and “Strange Feeling” (twenty-five R&B and seventy Pop).
By the mid-sixties Stewart had perfected his trademark sound. To the smooth, layered textures of Chicago Soul he added trills and doubled words in the manner of a scat singer or a trumpet player. He was an excellent improviser, and the record-buying public liked his style. His biggest R&B success was “Sitting In The Park” in 1965, written by Stewart and arranged by Phil Wright as a smooth, bouncy ballad.
The song reached number four on the R&B chart. His biggest hit on the Pop chart was a cover of George Gershwin’s “Summertime”, which Stewart arranged, creating a new feel for an old standard. It is a virtuoso performance, which took him to number ten on the Billboard Hot 100 Singles Chart and number seven on the Billboard R&B Singles Chart. During his time at Chess, Stewart also recorded several albums, two of which entered the album chart: “I Do Love You” (1965) and “Unbelievable” (1966).
Billy Stewart was a big man, and, like Fats Domino, he made reference to that fact in some of his songs. Unfortunately, his weight caused health problems. He was also involved in a motorcycle accident in 1969. He died, aged thirty-two, in 1970, when he was driving in North Carolina. His car left the road, struck a bridge and fell into a river, as a result of a mechanical fault.
Like Minnie Riperton, he made a big impression because he had a special vocal ability.
