A graduate of Morehouse College, Jennings studied with renowned artist Hale Woodruff. Jennings and his mentor, both WPA (Works Progress Administration) artists, collaborated on the creation of two murals. "The Negro in Modern American Life: Agriculture and Rural Life, Literature, Music and Art" and "The Dream" was once displayed (1934) at the David T. Howard School and the School of Social Work University in Atlanta. The images have since been destroyed.

Jennings, who remained close with Woodruff throughout his career eventually left Atlanta to attended the Rhode Island School of Design. When he matriculated from RISD, Jennings made history; he was one of the first African Americans to graduate from the institution. He firmly established himself as one of the best printmakers of his day and was noted for influencing the arts community’s recognition of printmaking as a major art form. Jennings did so in a powerful way. He is remembered, in part, for highlighting the harsh economic disparities and marginalization of the Black working class during the Depression era.

Jennings’ incredible technical skills as a printmaker was revisited in his work as a jewelry maker. At one point in his career, he served as the Imperial Pearl Company’s head jewelry designer and chief model maker where he was known for his African inspired images. Jennings was well respected for his technical expertise in casting precious metals using the lost wax method. His career as a printmaker was nearly cut short when Jennings suffered a potentially career ending injury to his dominant right hand. The artist is said to have re-trained himself and adapted to using his left hand.

Jennings’ legacy as one of the most prominent printmakers of his era, vicariously lives on through his daughter Corinne. She co-founded Kenkeleba House in 1974, a gallery that is dedicated “to celebrating and presenting the visual aesthetic and cultural legacy of African American artists and other artists of color that have been historically overlooked by the art world establishment and cultural mainstream.”