Bannister received his first oil painting commission, "The Ship Outward Bound", in 1854 from an African American doctor, John V. DeGrasse. Bannister's colleague, Jacob R. Andrews, created the commission's gilt frame. DeGrasse later commissioned Bannister to paint portraits of him and his wife. Patronage like DeGrasse's was critical to Bannister's early career, as the African American community wanted to support and highlight its contributions to high culture. African Americans found portraiture an "ideal medium" for expressing their freedom and opportunity, which is likely why Bannister's earliest commissions are mostly within that genre.