In 1960, Pinkney began working for The Rust Craft Greeting Card Company in Dedham, Massachusetts. Pinkney later worked at Barker-Black Studio, where he illustrated his first picture book in collaboration with Joyce Cooper Arkhurst called, "The Adventures of Spider: West African Folk Tales" (1964)"." He, along with a two other artists, opened Kaleidoscope Studio a few years later. Pinkney opened his own freelance studio, "Jerry Pinkney Studios", in 1968"." During the 1970s, Pinkney worked on the Black Heritage Stamp Series for the United States Postal Service. During the 1980s Pinkney began to receive additional recognition for his work, including a Coretta Scott King Award for his collaboration with author Patricia McKissack on "Mirandy and Brother Wind" (1989). Pinkney also collaborated with the National Geographic Magazine and the National Park Service on the topic of the Underground Railroad. Pinkney has also worked as an educator, teaching at colleges and universities like the University of Delaware, the Pratt Institute in Brooklyn, New York and the University at Buffalo, in Buffalo, New York. Jerry Pinkney and Gloria Jean Pinkney have four children: Troy, Brian, Scott, and Myles. Brian Pinkney and his wife Andrea Davis Pinkney also write books for children. The other Pinkney children, including Jerry and Gloria Pinkney's six grandchildren, all participate in the arts, which Gloria calls a continuation of “the Pinkney tradition.” Pinkney lives in Croton-on-Hudson in New York with his wife Gloria, where has worked out of his freelance studio, "Jerry Pinkney Studio", since 1971"." Pinkney got his start drawing in pencil and his early works were black and white productions. Currently, Pinkney uses a combination of watercolors and pencils for the majority of his work, along with other materials, such as, "pastel[s], color pencils, and Cray-Pas" In an interview, he stated watercolors are his "medium of choice." Pinkney's "intricate detail" is considered "rare" for a person who uses watercolors. Pinkney researches the subjects of his works for accuracy, such as the dress of the characters involved and the time periods. Pinkney also uses live models for establishing character poses. Pinkney has stated he likes to draw animals the most and to give these characters human features. Many of Pinkney's titles are on diverse themes and topics, such as African American history, and Pinkney has stated his stories are a way for him to "revisit" his childhood.