Raised in Champaign and brought up by his religious great-grandmother, Stringfellow would often travel north to Chicago where his parents lived. His father managed the Club De Lisa, a jazz nightclub on the South Side that was inclusive of non-binary and queer performers and patrons and was one of the only clubs in the city where Blacks were allowed to sit.

Stringfellow reflected on and infused his own experiences into his watercolors, collages, and sculptures, whether the works expressed the pride of vibrant communities in the South Side of Chicago, the radiant energy of jazz clubs, or the joyful exuberance of open-air baptisms at Urbana’s Crystal Lake.

Inspired to portray delight, Stringfellow once said, “I wanted to be an artist without a clenched fist in the air. I thought being a Black artist would be labeling myself, and besides, I was never mad.”