Sixteen years before the world would learn her nickname from Duke Ellington himself, Lil Greenwood was teaching elementary school in Prichard, the daughter of a Baptist minister who never imagined the voice she used in church would one day fill some of the country’s most storied jazz stages. Her story, largely unknown to many in the region she called home, was revisited in 2010 through the Mobile Bay Musician of the Month series, which named Greenwood its inaugural honoree for April of that year.
The recognition drew on Greenwood’s own account of her life, compiled from her website and interviews she had given over the years, and it traced a path from a Prichard classroom to the Purple Onion nightclub in San Francisco, and eventually to a recording session with Ellington and Billy Strayhorn that earned her a nickname she carried for the rest of her career: “One Take Lil.”
From a Prichard Classroom to a Train West
Greenwood was born in Prichard in 1924. Prichard, a city that sits just northwest of Mobile in Mobile County, was for much of the twentieth century a working-class community shaped by the rail and shipping industries that also drove much of the greater Mobile Bay area’s economy. Like many Gulf Coast communities of the era, its Black churches served as centers of both spiritual and cultural life, and it was in that setting — as the daughter of a Baptist minister — that Greenwood first learned to sing.
She went on to attend Alabama State College, now Alabama State University, a historically Black institution in Montgomery that has produced generations of Alabama educators, ministers and civic leaders since its founding in 1867. After completing her studies, Greenwood returned to Prichard to teach elementary school, a common path at the time for young Black women from the region who pursued higher education.
In 1948, at 24 years old, Greenwood left that teaching job and boarded a train for San Francisco. She had planned to reunite with her husband, who was completing his service in the Army, and to begin a new chapter of married life on the West Coast. According to her account, that reunion did not go as planned. Her husband reportedly asked her to return to Prichard to raise a family, a request she declined. Their relationship remained complicated in the years that followed; when he died, one of his final wishes was for Greenwood to sing at his funeral.
Finding a Voice in San Francisco’s Jazz Clubs
Rather than return home, Greenwood stayed in San Francisco and found work singing at the Purple Onion, a nightclub in the city’s North Beach neighborhood that, through the 1950s and into the 1960s, became known as a launching pad for entertainers working in comedy, folk and jazz. The venue would later be associated with performers such as the Kingston Trio and a young Phyllis Diller, reflecting the eclectic, competitive club scene Greenwood entered as a newcomer from Alabama.
By her own account, Greenwood quickly discovered that the hymns and spirituals she had grown up singing in Prichard’s churches were not what San Francisco jazz audiences wanted to hear. She adapted, learning new material and eventually writing her own songs. Among the compositions she developed during this period was “Walkin’ and Singin’ the Blues,” a song that would later become central to the most consequential night of her career.
Greenwood also began recording during these years. She cut rhythm and blues singles for Modern Records in 1950, and followed with sessions for King Records and its subsidiary Federal Records in 1952 and 1953. Modern, King and Federal were among the most active independent labels recording Black artists in R&B and blues genres during the postwar era, part of a wave of small labels — also including Chess, Specialty and Atlantic — that captured and commercialized sounds emerging from Black communities across the country. Those early Greenwood sides were largely forgotten for decades until Ace Records, a British reissue label known for compiling vintage American R&B and rock and roll recordings, collected them in 2004 on the CD “Walking and Singing the Blues.”
A Chance Encounter With Duke Ellington
The turning point in Greenwood’s career came in 1956, when Duke Ellington caught her performance at the Purple Onion. Ellington, already one of the most celebrated bandleaders and composers in American music, led an orchestra that had been a fixture of jazz since the 1920s, built on collaborations with musicians and arrangers who helped define the swing and big-band eras. Chief among his collaborators was Billy Strayhorn, the composer and pianist whose partnership with Ellington produced some of the era’s most enduring jazz standards.
According to Greenwood, Ellington approached her about a week after seeing her perform and invited her to Manhattan to meet him and Strayhorn. When she arrived at Strayhorn’s apartment, she found that the two men had already added new lyrics and verses to her song “Walkin’ and Singin’ the Blues.” After a dinner together, they invited her to sit in on a midnight recording session. The session reportedly required only a single take, prompting Ellington to give her the nickname that would follow her for the rest of her performing life: “One Take Lil.”
The pace of what followed, by Greenwood’s telling, was remarkable. Within days she was performing with the Ellington Orchestra in Boston, and within two weeks she was on stage at the Newport Jazz Festival, one of the most prestigious jazz gatherings in the country. First held in Rhode Island in 1954, the festival quickly became a proving ground for jazz artists and a showcase where legendary live recordings — including Ellington’s own celebrated 1956 Newport performance — helped shape the genre’s postwar resurgence. “Walkin’ and Singin’ the Blues” was subsequently released as the B-side of a single, giving Greenwood’s composition national distribution through one of the era’s most prominent bandleaders.
Life Among Jazz’s Biggest Names
Greenwood worked with the Ellington Orchestra, and later with Mercer Ellington, Duke’s son and eventual successor as the orchestra’s leader, into the early 1960s. Touring and performing alongside the Ellington organization placed her in the orbit of many of the era’s most significant jazz figures. Greenwood said she performed and socialized with artists including Billie Holiday and Sarah Vaughan, two of the most influential vocalists in American music history, though she maintained she never smoked, drank or used drugs during those years.
“I always imagined that my Daddy was looking over my shoulder and I never wanted to let him down or disappoint him,” Greenwood said of that period. “I never preached to my friends about their habits, but I did usually leave the parties before they did.”
After her years with the Ellington organization, Greenwood continued to record, though less frequently, for labels including NRC, Reprise and Tangerine — the latter a label founded by Ray Charles in the early 1960s to give the singer greater creative control over his output and, in some cases, to support other artists he championed. Greenwood also expanded into television during this era, appearing on programs including “The Tonight Show,” “Good Times” and “The Jeffersons,” three of the most-watched network television programs of their respective periods and an indication of how her career had broadened beyond live jazz performance and recording into mainstream entertainment.
A Return to the Gulf Coast
In 2002, the retrospective collection “Walking and Singing the Blues” brought renewed attention to Greenwood’s early 1950s recordings, introducing a new generation of listeners to material that had been out of print for decades. Around this period, Greenwood returned to the Mobile area, reconnecting with the region where her career had begun as a young teacher and church singer decades earlier.
In 2007, she recorded “Back to My Roots” with David Amram, a composer, conductor and multi-instrumentalist known for his wide-ranging career across jazz, classical and folk music, as well as his associations with Beat Generation writers and musicians in the 1950s and 1960s. The collaboration reflected Greenwood’s continued connection to the musical roots she had carried with her since childhood, even as her career had taken her far from Prichard and back again.
By the time of her selection as the inaugural Mobile Bay Musician of the Month, Greenwood had continued performing regularly at local festivals and small venues, including Serda’s, a longtime Mobile coffeehouse that has served as an intimate performance space for musicians across genres. Her continued presence on the local circuit offered area audiences a rare opportunity to hear a direct link to the golden era of American jazz and rhythm and blues, performed by an artist who had shared stages with some of the genre’s most celebrated names.
A Musical Legacy Rooted in South Alabama
Greenwood’s career illustrates a pattern common to many Gulf Coast musicians of her generation: a foundation built in local churches and schools, a departure to pursue opportunity in larger cities, and — for some — an eventual return home that reconnects national or international careers with the communities that shaped them. Mobile and the surrounding Gulf Coast region have produced a number of musicians whose influence extended well beyond South Alabama, and local recognition programs such as the Musician of the Month designation have served to document and celebrate those contributions, particularly for artists whose achievements might otherwise go unrecorded in mainstream music histories.
For a city and county with deep musical roots — from church choirs and brass bands to blues clubs and jazz combos — stories like Greenwood’s serve as a reminder that the Gulf Coast’s contribution to American music runs through individual lives as much as through institutions. Her journey from a Prichard classroom to a midnight session with Duke Ellington, and back again to the coffeehouses and festival stages of her home region, stands as one such thread in that broader history.
2010 Health Update: A Stroke and an Indefinite Hiatus
An update on Greenwood in late 2010: earlier that year she suffered a stroke and had been recovering at a local healthcare facility, placing her performing career on indefinite hiatus. Visitors who saw her that fall reported she was recovering well and in good spirits.
The news arrived as Greenwood marked a milestone birthday — she turned 86 on November 18, 2010. Friends and fans across Mobile wished her a continued recovery and hoped to hear that voice again before long.
Lil Greenwood, 1923-2011
Update, July 2011: Lil Greenwood has died at 88. The Prichard-born singer passed away on July 19, 2011, closing a career that carried her from an elementary-school classroom in Prichard to the Purple Onion in San Francisco, R&B sides for Modern, King and Federal Records, and two years touring with Duke Ellington and his orchestra — where a one-take midnight session with Billy Strayhorn earned her the nickname “One Take Lil.”
The stroke she suffered in 2010 had already ended her performing days. She returned to Mobile late in life and recorded Back to My Roots there in 2007 with David Amram, including a 2007 performance of that material with the E.B. Coleman Orchestra at the Saenger Theater. Her early-1950s recordings remain available on Ace Records’ 2004 collection Walking and Singing the Blues.