In the late 1960s, Hobbie sold distinctive artwork of a cat-loving, rag dress-wearing little girl in a giant bonnet to American Greetings. This series of illustrations became popular, and her originally nameless character became known as "Holly Hobbie."
As a contract artist, Hobbie worked with the Humorous Planning department at American Greetings under art director Rex Connors, who was responsible for launching "blue girl" as the most identifiable of the Hobbie characters. Also working in Humorous Planning at that time (1973, 1974) was Bob Childers, a veteran humorous concept artist and designer. Childers insisted that there should be a doll. Since no one seemed to listen, Childers went home and, on his own time, hand-stitched the first prototype and presented it to Connors. Rex Connors then took the doll to Tom Wilson, Creative Vice President, after which American Greetings approached Knickerbocker Toys concerning the Holly Hobbie license.
In 1974, Knickerbocker Toys licensed the Holly Hobbie character for a line of rag dolls, which were a popular toy for young American girls for several years. Holly Hobbie products are now once again being marketed by American Greetings in association with Carlton Cards.
In 1980, Holly was featured in a novel by Richard Dubelman entitled The Adventures of Holly Hobbie. In this book, Holly Hobbie is a ghost who lives in a painting that was painted in 1803. She comes out of the painting to help a descendant, Liz Dutton, find her missing father, an archaeologist who has vanished in Guatemala.