Attending The High School of Music & Art, he was a classmate of future comic book artist and editor Joe Kubert.

[7] Hollingsworth graduated from City College of New York in 1956, Phi Beta Kappa, as a fine arts major, and earned his master's degree there in 1959.

[4][8] In the mid-1950s, while still a student, he worked on newspaper comic strips including Kandy (1954-1955)[9] from the Smith-Mann Syndicate, as well as Scorchy Smith (1953-1954)[9] and, with George Shedd, Marlin Keel (1953-1954).

[1] As a painter, his subjects included such contemporary social issues as civil rights for women and African Americans, as well as jazz and dance.

[11] In the summer of 1963, Hollingsworth and fellow African-American artists Romare Bearden and William Majors formed the group Spiral in order to help the Civil Rights Movement through art exhibitions.