The Four Stewart Brothers appeared on their own radio show Sunday mornings in Washington DC for five years. The oldest of the brothers was Billy, who was only 12 years old when they began singing together in the early fifties. Billy was an excellent piano player and sometimes filled in at shows by the Rainbows. Bo Diddley witnessed Billy playing piano at one of his shows and recruited Billy to join his backup band. Billy began recording for Chess Records, and Bo played guitar on his 1956 recording of Billy’s Blues.
Billy recorded a few singles that reached #79 and #70 on the Hot 100 in 1962 and 1963. He finally cracked the top forty in 1965 with two singles he wrote himself. His first top forty single was I Do Love You, which reached #26 on the Hot 100. The follow-up single, Sitting In The Park, did even better, and I instantly recognized it even though it peaked at only #24.
His next single quickly came and went, but later in 1966 he had the biggest hit of his career. He covered the song Summertime from the 1935 play Porgy And Bess. He did a more uptempo version of the song and included some scatting throughout, and his single reached #10 on the Hot 100. The record also made it to the top ten on the R&B chart. He included a longer version of the song on his next album.
Doris Day topped the Hot 100 in 1954 with her version of Secret Love. Billy recorded a cover of the song for his next single, using an arrangement that was similar to his previous hit. Sadly, Billy’s version could get no higher than #29. Freddy Fender later covered the song in 1975, and his Tex-Mex single reached #20 on the Hot 100.
Billy kept recording through the rest of the sixties, but never had another major hit.
Billy’s weight began to cause him health problems, and he developed diabetes in the late sixties. He suffered injuries from a motorcycle accident in 1969. He and three passengers in his car died in 1970 after he accidentally drove his car off a road near a bridge and the car landed in a river.
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