Biography
Billy Stewart, born William Larry Stewart II on March 24, 1937, in Washington, D.C., emerged as a distinctive voice in American rhythm and blues during the 1960s. Raised in a musically gifted family, Stewart began performing at age 12 with his brothers as The Four Stewart Brothers, singing gospel and hosting a weekly radio show on WUST-AM in Washington, D.C. This early exposure, combined with piano lessons from his mother, laid the foundation for his musical career. Stewart transitioned to secular music by filling in for The Rainbows, a local vocal group, where he connected with future stars like Don Covay and Marvin Gaye.
Stewart's big break came when rock and roll legend Bo Diddley discovered him playing piano in Washington, D.C., in 1956. Diddley invited Stewart to join his band and helped secure a recording contract with Chess Records, where Stewart's debut single, 'Billy's Blues,' featured Diddley on guitar. Stewart's unique vocal style—marked by rapid word doubling, scatting, and improvisational trills—set him apart from his contemporaries. He achieved commercial success with hits such as 'I Do Love You,' 'Sitting in the Park,' and his radical, virtuosic rendition of George Gershwin's 'Summertime.' Despite his growing acclaim, Stewart's career was cut short when he died in a car accident in North Carolina on January 17, 1970, at the age of 32.
Stewart's legacy endures through his innovative vocal techniques and his influence on the soul genre. He was posthumously inducted into the Washington Area Music Association Hall of Fame in 2002 and the National Rhythm & Blues Hall of Fame in 2021, recognized as a creative genius and a visionary whose contributions helped shape the sound of classic soul and R&B.
Fun Facts
- Billy Stewart's radical version of 'Summertime' is considered one of the most innovative soul interpretations of a standard, featuring his signature trilling and scat singing.
- He and his brothers hosted their own live radio show every Sunday for five years on WUST-AM in Washington, D.C., while still teenagers.
- Stewart was discovered by Bo Diddley while playing piano in a Washington, D.C. club—a chance encounter that launched his recording career.
- He suffered from diabetes and weight problems throughout his life, which, along with a tragic car accident, contributed to his early death at age 32.
Musical Connections
Mentors/Influences
- Bo Diddley - Discovered Stewart playing piano, invited him to join his band, and facilitated his first recording contract. ('Billy's Blues' (1956, Chess Records)) [1956–late 1950s]
- His mother - Taught Billy and his brothers piano and led the Stewart Gospel Singers. (Stewart Gospel Singers performances) [1940s–1950s]
Key Collaborators
- The Four Stewart Brothers - Early gospel group with his siblings; performed on radio. (WUST-AM radio show) [1949–mid-1950s]
- Don Covay - Bandmate in The Rainbows, a D.C. vocal group. (Performances with The Rainbows) [mid-1950s]
- Marvin Gaye - Met and performed with Stewart in The Rainbows and The Marquees. ('Billy's Heartache' (backed by The Marquees)) [late 1950s]
- Billy Davis - A&R man at Chess Records who worked with Stewart on his early 1960s recordings. ('Fat Boy', 'Reap What You Sow', 'Strange Feeling') [early 1960s]
Artists Influenced
- Contemporary soul and R&B vocalists - Stewart's unique vocal techniques—scatting, trilling, and word doubling—became influential among later soul singers. (General influence on soul genre) [1970s–present]
Connection Network
Discography
Albums
| Title | Release Date | Type |
|---|---|---|
| I Do Love You | 1965-01-01 | Album |
| Cross My Heart | 1974-01-01 | Album |
| Unbelievable | 1965-01-01 | Album |
| At His Best | 2018-01-30 | Album |
| Essential Classics, Vol. 786: Billy Stewart | 2025-04-23 | Album |
| Billy Stewart Teaches Old Standards New Tricks | 1967-08-01 | Album |
| I Do Love You | 2023-01-06 | Album |
| At His Best | 2018-01-30 | Album |
| Unforgettable | 2017-10-11 | Album |
| Wedding Bells | 2016-08-12 | Album |
| Fat Boy | 2014-08-23 | Album |
| Chanting Rock | 2013-12-06 | Album |
| Unbelievable + Cross My Heart (2 Albums on 1) | 2011-01-01 | Album |
| I Do Love You | 1997-01-01 | Album |
Top Tracks
- Sitting In The Park (I Do Love You)
- I Do Love You (I Do Love You)
- Cross My Heart (Cross My Heart)
- Sitting In The Park - Single Version (One More Time : The Chess Years)
- I Do Love You (One More Time : The Chess Years)
- Strange Feeling (I Do Love You)
- Summertime
- Summertime
- Summertime (Unbelievable)
- Sitting In The Park - Single Version
External Links
Tags: #2008-universal-fire-victim, #chicago-soul, #jazz-pop
References
Heard on WWOZ
BILLY STEWART has been played 2 times on WWOZ 90.7 FM, New Orleans' jazz and heritage station.
| Date | Time | Title | Show | Spotify |
|---|---|---|---|---|
| Nov 13, 2025 | 15:39 | Fat Boyfrom 20TH CENTURY MASTERS - THE MILLENNIUM COLLECTION; BILLY STEWART | Bluesw/ DJ Giant | |
| Oct 30, 2025 | 14:11 | SITTING IN THE PARKfrom SINGLE | Bluesw/ DJ Giant |