Billingsley was born in Wake Forest, North Carolina, and raised there in his earliest years.
As a young boy, he learned to draw in order to emulate his older brother, who studied fine arts.
[2] By 1988, he was freelancing in advertising and public relations; doing television commercials, posters and animation; and working for magazines such as Ebony.
In addition, Billingsley received the Humanitarian Award from the American Lung Association of Southeast Florida in 1999.
[7] Billingsley's most prestigious recognition came when he was awarded the 2020 Reuben Award by the National Cartoonists Society,[8] placing him in the company of great cartoonists such as Charles Schulz, Garry Trudeau, Jerry Scott, and Roz Chast.