His parents, Sally (1815–1880) and Bill Calloway (1805–1860+), were slaves on the plantation of George Hartwell Traylor (1801–1881), a white cotton grower.
While the end of the war ensured his legal emancipation, Traylor remained entrapped in the economic structures of the South's Jim Crow laws.
[citation needed] While documenting the details of Traylor's early life remains difficult, scholars have noted that he fathered a number of children over his lifetime.
"[5] For 75-year-old Traylor, it would prove to be a challenging new beginning, but he rented a room and later a small shack, and found work to support himself.
In February 1940, New South, a cultural center that Shannon founded, launched the exhibit Bill Traylor: People’s Artist.
Notably, Alfred Barr, the director of MoMA, offered to purchase several drawings for the museum’s collection, as well as his own personal one.
As a collection, Traylor’s drawings depict his experiences and observations from rural and urban life in pared down repeated symbols, shapes, and figures.
While some pieces focus on a single animal, like a dog or snake, other paintings offer composed scenes of individuals gathering by a fountain or working on a farm.
[citation needed] His works range from simple single-figured depictions to more compositionally complicated pieces of multiple silhouetted figures.
[citation needed] In 1979 Richard H. Oosterom agreed to hold a solo exhibit featuring Bill Traylor's pieces.
[13] It wasn’t until Traylor's 1982 debut at the Corcoran Gallery of Art in Washington D.C. that the audiences started to note the significance of his work.
Curators Jane Livingstone and John Beardsley included 36 of Traylor's pieces in the landmark exhibition Black Folk Art in America 1930-1980.
Scholars and curators have moved away from labeling him as a "primitive" or "outsider" artist, and have instead chose to focus on his prominence and significance within 20th-century American art.
In 2005 the Studio Museum in Harlem launched the exhibit Bill Traylor, William Edmondson, and the Modernist Impulse.
Roberta Smith, from The New York Times, described the coupled exhibits as "offer(ing) total immersion in his late-life burst of genius.
[21] In 1942, when detailing Traylor's exhibitional debut, local journalists heralded the "primitive" and "African" quality of his artwork.
The Montgomery Advertiser published an article entitled "The Enigma of Uncle Bill Traylor: Born A Slave, Untutored in Art, His Paintings Are Reminiscent of Cave Pictures – And Picasso.
In 2013 the American Folk Art Museum hosted a full-day symposium, Bill Traylor: Beyond the Figure, to discuss his complicated legacy.
"To discount" his personal struggles "is to ignore what makes Traylor not only a noteworthy artist, but also an eloquent annalist of a nation’s history: its brutality.
[28] The symposium held in 2019, in conjunction with the Traylor retrospective at Smithsonian Museum of American Art, discussed how new information about his visual record of African-American life could provide insight into the story of the US.
[32] The 2009 publication of Mechal Sobel's book Painting a Hidden Life: The Art of Bill Traylor sparked considerable controversy.