A former student at Frankfurt’s Kentucky Normal and Industrial Institute for Colored Persons (now Kentucky State University), Wilson left Kentucky for Chicago. He attained a degree at the Art Institute of Chicago in 1923—an institution that served as a training ground for other famed artists such as Richmond Barthe and Elder Cortier.

Wilson briefly worked as a commercial artist in Chicago. His arrival was during a tumultuous time in the city’s history. The artist explained that "he arrived, [during] a race riot that would eventually claim dozens of lives broke out downtown.” Concerned for his safety, Wilson recalled that, “I couldn’t go downtown to the Art Institute. They were shooting and carrying on.” Wilson, eventually left Chicago for New York.

He arrived in Harlem in 1928, in the midst of the “most influential movement in African American literary history.” Artists of all genres aspired to “reconceptualize the Negro apart from the white stereotypes that had influenced Black peoples’ relationship to their heritage and to each other.” Black artists found that most mainstream galleries were inhospitable. However, enjoyed welcome respite with entities such as the Harmon Foundation an institution that dedicated itself, in part, to increasing acceptance of their work.

Wilson was unable to solely rely on the Foundation to meet his needs. In the mid 1930s to 1940, like several of his contemporaries who struggled to make ends meet, he secured employment through the government’s Works Progress Administration Federal Arts Project (WPA). One of the benefits of working for the WPA was that it gave Wilson the opportunity to commune with more Black artists. That interaction perhaps had some influence on the artist’s style. Ellis recalls that, “I just cut out completely from anything that looked like a portrait,” he said. “It was freer. I was astounded. I just hit upon something.” Wilson’s new found freedom was supported in part by various sources of funds that allowed him the opportunity to travel and gain new experiences.

In the mid 1940’s Ellis traveled throughout the south where created a series of genre paintings that captured “the Negro,” --one of the artist’s preferred subjects. Ellis was impressed by the sheer dignity of their presence and performance of daily life activities. Ellis also sought inspiration abroad. He made several trips to Haiti where he was impressed that, “although [Haitians] were Black, I couldn’t understand them—they all spoke Creole and French. All that excited me.” Ellis was inspired by the tropical atmosphere and the rich Caribbean cultural music, the drumming, the dancing, they were very artistic.”

Some of the more poignant examples of the artist’s work from this period highlight the artist’s shift from more representation images toward abstraction. Though Ellis was at the culmination of his popularity during this time, interest in his work began to decline in the 1950s. It was not until the 1980 that Wilson experienced a revival of interest in the 1980s when his "Funeral Procession" image was featured on an episode of The Cosby Show. Like some of Wilson’s other images, in "Funeral Procession," he employed the use of silhouetted figures and distortion—rendering figures in the composition without facial features and relegating their shapes to geometrically inspired forms.

Subsequently, Ellis’ work was featured in numerous national exhibitions.