Home » Black Music Sunday: Remembering singer Billy Stewart

Black Music Sunday: Remembering singer Billy Stewart

Billy Stewart was a stellar R&B singer with a unique vocal style of scatting and word doubling who doesn’t get enough props when we’re discussing the “greats” of the genre. We’re celebrating his birthday and remembering a performer who brought joy to all who heard him, though he has often been overlooked when discussing great soul singers.

Stewart was born on March 24, 1937, in the nation’s capital—which would be his home base for his entire life, though he recorded his major hits for Chess Records in Chicago. Tragically, his hit-making career was cut short in January 1970, when at the age of 32, he was in a tragic automobile accident that killed him and three of his band members: Norman P. Rich, William Cathey, and Rico Hightower.

But Stewart’s music lives on, and with hits like “Summertime,” “I Do Love You,” and “Sitting in the Park,” he carved a place in many of our hearts. Join me in celebrating his memory and his music today.

”Black Music Sunday” is a weekly series highlighting all things Black music, with over 200 stories covering performers, genres, history, and more, each featuring its own vibrant soundtrack. I hope you’ll find some familiar tunes and perhaps an introduction to something new.

Dr. Otis D. Alexander’s Black Past biography covers Stewart’s early years:

At the age of nine, Stewart played the piano. At 12, he began singing gospel with his three younger brothers. All of them were taught piano by their mother and they were known as “the Stewart Gospel Singers” under the direction of Idabel Stewart. In 1955, Billy Stewart graduated from Armstrong Technical High School, an all-black high school in then racially segregated Washington, D.C. 

The legendary guitarist Bo Diddley discovered Stewart’s gift and talent as a pianist in 1956 when he saw his performance with the R&B group, the Rainbows, and introduced him to Chicago-based Chess Records’ talent scouts.

The Rainbows were the subject of a 2003 story by Washington Post music critic Richard Harrington.

A Pot of Gold for Fans of the Rainbows

In the history of soul music in Washington, the Rainbows are remembered less for their several minor hits than for a trio of major talents who were, at one point or another, part of the vocal ensemble in the mid ’50s. One, Marvin Gaye, is a certified giant. Another is Don Covay, an often-overlooked artist whose song closet has been raided by everyone from Aretha Franklin to the Rolling Stones. The last is Billy Stewart, a superb vocalist who died more than three decades ago and is now sadly forgotten.


Pianist and singer Billy Stewart, the third of the Rainbows’ major talents who was inducted into the WAMA Hall of Fame earlier this year, was a distinctive stylist whose stuttering delivery and word-doubling technique earned him the nickname “Motormouth.” Born here in 1937, Stewart started in gospel, moved to secular music with Rainbows and, under the tutelage of Bo Diddley, cut his first single, “Billy’s Blues,” for Chess in 1956. He was backed by the Marquees on 1957’s “Billy’s Heartache.” Other early singles included “Fat Boy” (Stewart weighed 350 pounds) and “Reap What You Sow.”

I find the background on Washington, D.C., as a source of doo-wop and R&B talent to be quite interesting. Researching Stewart led me to The African American Music Association’s “The Nations Capital—DooWop from the Streetcorner to the Stage,” which led me next to a profile of Stewart.

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”.

Though I went to Howard University and hosted a radio show in D.C. for several years, I was much more aware of D.C. as the home of Duke Ellington. My New York City chauvinism led me to think of my hometown as the only home of doo-wop. 

I stand corrected. 

Here’s that recording of “Billy’s Blues,” with Bo Diddley:

According to his biographers, Stewart struggled with his weight issues and diabetes for his whole adult life. Two of his songs directly referenced his weight. He recorded “Fat Boy” in 1962, and the poignant “A Fat Boy Can Cry” in 1964.

“Fat Boy” is also the name of the documentary about his life. More on that in a moment.

Stewart left Chess Records to record on the Okeh label, and didn’t return to Chess until 1965. Michael Jack Kirby, music historian and oldies radio programmer at Way Back Attack, offers a detailed look at Stewart’s transition to hit records.

Billy was interested in returning to Chess, which by that time had employed Roquel “Billy” Davis, a former Detroit producer and songwriter (for Motown and a few other small labels); Davis had freelanced for Chess before becoming a permanent fixture and for Stewart the timing was right (a short,skinny guy, Davis has said he felt he complemented the hefty singer). In January 1962, a strong two-sider was recorded: “Fat Boy,”an autobiographical love song of sorts (‘…I was her pride and joy…and she was in love-a with-a fat boy…’), and “Reap What You Sow,” which set a standard for Stewart’s type of tongue-twisting exultation (‘Baby, baby, a-baby, a-baby come-a back-a home, wo-o-o-o,o-o-o-o-o-o-oooh…’); backing vocals were provided by the Four Jewels, a girl group from Washington, D.C. that had a hit, “Opportunity,”a couple of years later as The Jewels. After several months on the shelf, the single was issued and “Reap” became a top 20 R&B hit and minor pop charter.


A December 1964 recording session produced two big hits, both Stewart compositions enhanced by male vocal backing (his brother Johnny taking part). “I Do Love You” is an early example of the smooth Chi-soul trend developing at the time, Billy’s extra-syllable style running throughout. Going top ten R&B and top 30 pop in May 1965, the chart feat was repeated two months later with “Sitting in the Park,” sonically similar but lyrically more somber (‘Sitting here on the bench…with my back against the fence…wondering-a if I-I-I…have any sense, girl…’). The era’s “overweight lover” unapologetically tailored his music to female fans with “How Nice It Is,” the excessively bubbly “Because I Love You” (‘I’ll follow a rainbow…bring you a pot of gold…la-la-la-la…’), “Mountain of Love” and “Love Me.” Yet in 1966, Stewart grew tired of such passion plays and decided to try something a little different.

“I Do Love You” brings back lots of memories for me. It got played at every “blue light” party I went to that summer.

This amazing live version of “I Do Love You” was recorded in Philadelphia in 1967, at a show at the Nixon Theater put together by Philly DJ Jimmy Bishop

The full album is available on YouTube.

Stewart followed his first major hit with another, “Sitting In The Park,” also in 1965.

Blogger boppinbob at “From The Vaults” wrote about how Stewart’s cover of “Summertime” got made in late 1965, when A&R man and producer Billy Davis thought “Stewart doing an album of standards in his vocal style” would bring him into the mainstream and appeal to pop music listeners. The song, from “Porgy and Bess,” had brought him a victory as a teen in “a local contest.”

“Way Back Attack’s” Kirby adds his take on “Summertime”:

Billy’s lyrical twists aren’t easy to describe, but his extended tongue-stutter certainly must be one of the most recognizable song intros of all time and his ad-libbed line ‘Little darlin’ do not let a tear fall-a from your eye-eye-eye-eye-eye…’ makes for a spectacular ending. Rules were bent; Davis instructed the session band to follow whatever Billy did, adjust on the fly, make it work! (Seeing it all unfold, he must have thought, “What kind of a monster are we creating?”). Even though the song had been performed on the stage for three decades and in the Academy Award-winning 1959 film starring Sidney Poitier and Dorothy Dandridge, despite its having been a top seller several times (for Billie Holiday in 1936, Sam Cooke in ’57 and in 1960s remakes by The Marcels, Rick Nelson and instrumental act The Chris Columbo Quintet), this latest “Summertime” was the hottest version yet, Billy Stewart’s biggest hit, a pop and R&B smash, top ten in the heat-scorched month of August 1966. Anyone who’s heard it…even just once…has never forgotten it!

This live performance is from the Dick Clark-produced “ Where The Action Is” in 1967.

As promised earlier: A long-awaited documentary on Stewart is helping ensure he doesn’t fade into obscurity. John Kelly wrote about “Fat Boy: The Billy Stewart Story” for The Washington Post in 2021.

A new documentary celebrates Billy Stewart, D.C.’s unique R&B singer

Stewart played piano in Bo Diddley’s band, then struck out on his own. He looked impressive — his “Fat Boy” nickname was not ironic — and sounded impressive, with a distinctive vocal style he based on his love of Caribbean music.

“That’s what he told Dick Clark,” [director Beverly] Lindsay-Johnson said.

You hear it best on his version of the Gershwin song “Summertime,” in which Stewart trills and scats to a horn-driven background. Quentin Tarantino included the song on the soundtrack to “Once Upon a Time in Hollywood.”

To record his songs, Stewart traveled to Chicago, the home of Chess Records, but he always lived in Washington.

“Billy was a native Washingtonian to his heart,” Lindsay-Johnson said.

The documentary grew out of a program Lindsay-Johnson co-hosted in 2016 at the Martin Luther King Jr. Memorial Library. It explored the careers of Stewart and another musical Washingtonian, Van McCoy. With funding from Humanities DC, she started work on Stewart’s story in 2019, interviewing relatives, musicians he worked with at Chess and one he shared a bus with in a Dick Clark Caravan of Stars tour: Jerome Anthony “Little Anthony” Gourdine of Little Anthony and the Imperials.

Music journalist T. Watts reviewed the film for California’s Lake County News in 2021.

Award-winning documentarian turns to the story of Billy Stewart

Emmy Award-winning documentarian Beverly Lindsay-Johnson is the director/producer of the new film on Soul/Rhythm & Blues legend Billy Stewart.

Stewart, to the uninitiated, was the ebullient, rotund, piano-playing crooner from Washington, D.C., whose highly original style of singing has not been replicated before or since. One writer described Stewart’s vocal stylings as the R&B equivalent of scat singing. His take on two songs in particular; Gershwin’s “Summertime,” and “Secret Love,” made famous by Doris Day, altered the auditory receptors of American musical taste. 


Skillfully woven in are interviews with many stars of R&B and Doo-Wop who witnessed the artistry of Stewart; Anthony Gourdine of Little Anthony and The Imperials, Herb Fame, of Peaches & Herb, Mitty Collier (“I Had A Talk With My Man Last Night”), The Bay Area’s Own – Queen of the West Coast Blues Sugar Pie DeSanto, (DeSanto wrote a song for Billy Stewart during her seven-year tenure with Chess), Grace Ruffin of the Jewells, Music Journalist Mike Boone, and Emanuel Raheim of the Disco/R&B group GQ. The resulting marriage of the filmmaker’s vision of the preservation of yet another epoch of Black expression is richly deserving of the international acclaim PBS is affording this documentary

Watch the entire film here, courtesy of PBS. It’s worth 56 minutes of your time!

The documentary explores the journey of the singer from his days as a piano player to a famous R&B balladeer. His style of singing was untouchable as he mastered word doubling and scatting throughout his songs and performances. 

I hope you’ve enjoyed this celebration of Billy Stewart on his birthday. And I’m curious: Was this tribute an introduction for you, or a fond memory? Meet me in the comments to let me know, and for a ton more great music!

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March 2024