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Billingsley contributed early cartoons to Kids, a magazine "by kids for kids" published in Cambridge, Massachusetts and then in New York City from 1970 to 1975 under the co-editorship of Jenette Kahn, future president and editor-in-chief of MAD Magazine and DC Comics. Those intricately detailed drawings already showed a cartoonist in the making.
After graduating from the High School of Music and Art in Manhattan, he attended the School of Visual Arts on a four-year scholarship. After graduating, he began an internship at Walt Disney Studios in 1979.
Billingsley drew a nationally syndicated strip called Lookin' Fine from 1979 to 1982.
By 1988, he was free-lancing in advertising and public relations; doing television commercials, posters and animation; and working for magazines such as Ebony. In October of that year, King Features Syndicate introduced Curtis.
Billingsley acknowledges that Wee Pals creator Morrie Turner, the first black cartoonist in national syndication, opened the door for Curtis and other strips. He also credits Will Eisner, creator of The Spirit, for encouraging Billingsley to stretch out artistically. "He always told me to reach out and do more than I thought I could. I continually draw strength when I relive his teachings," said Billingsley.
Billingsley has received several awards, including the President's Award in 2000, during the conference between the American Lung Association and the Canadian Lung Association in Toronto, Canada. In addition, Billingsley received the Humanitarian Award from the American Lung Association of Southeast Florida in 1999.
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