In the early 1970s, 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 immensely popular and her originally nameless character became known as "Holly Hobbie".

Holly Hobbie, as a contract artist, 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 Hobby characters. 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 Hobby 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.

In 2006, a redesigned Holly Hobbie was launched as part of a spin-off product line called "Holly Hobbie and Friends". She was featured in a movie titled Surprise Party. The movie aired on Nick Jr. and is available on DVD. The traditional line still exists, with the back story being that the "original" Holly is the great-grandmother of the "new" Holly.

Mattel released a brand new Holly Hobbie doll line during 2006, which includes Holly (blue eyes & blonde hair), Amy (green eyes & red hair), and Carrie (brown eyes & black hair). The dolls feature an all new face sculpt, a new body style, and flat feet. There is also a series of smaller Holly, Amy, and Carrie figures; each of these figures arrives with a farm animal (Holly has a dog named Doodles, Amy has a pig named Chedder, and Carrie has a cat named Bonnett). Separate doll outfits are being sold; each outfit can be customized by the child or the collector. This new doll line is cute and craft-themed. Holly Hobbie (the cartoon) also has three popular songs, two sung in her own voice, "Just Like You" and "The Things That Make You Special", LeAnn Rimes sang "Twinkle in Her Eye", the theme song.

Toot & Puddle (a creation of the real Holly Hobbie) are best friends, even though Toot likes to travel and Puddle likes to stay at home.

Books

There are several books of their adventures, including:

• Toot & Puddle
• A Present for Toot
• You Are My Sunshine
• I'll Be Home For Christmas
• Top of the World
• Charming Opal
• The New Friend
• Wish You Were Here
• The One and Only
• Let It Snow
• Puddle goes to Africa

A "Toot & Puddle" holiday story, I'll be Home for Christmas, was released on DVD by National Geographic.

Toot & Puddle Television Show

A TV series was made in 2008 by Mercury Filmworks, National Geographic Kids, Treehouse TV and Noggin with the pilot Free Falling Friends/Carried Favors. It ended in 2009, but still reruns are shown. Holly Hobbie also directed the series. In the show, Toot & Puddle live in Pocket Hollow. In each episode they learn about a different place or culture. Toot usually goes on a trip to a foreign country, but sometimes Puddle comes along. Every time Toot goes on a trip, Toot & Puddle together say "A boomerang flies, but always returns home where it belongs."On each trip Toot sends a postcard to Puddle. He learns many things on his trips and has many adventures so he shares them with everyone at home.