During each half-hour segment, Pappy and other characters danced, sang, taught life lessons and other children's television fare but the main focus of the show was watching Pappy draw pictures. The camera was positioned directly above his paper and he would carefully explain the purpose of each technique used. The purpose was for children viewers to be able to follow along with Pappy and create the same image as he did. Viewers who sent in their artwork, had their drawing shown during the "Hall of Frames" segment near the end and the closing credits. When shown on public television, WCNY in Syracuse, New York presented the show, which was produced by the non-profit Craftsmen and Scribes' Creative Workshop and Creative Media Solutions TV, also based in Syracuse, New York. In fact, the P.O. Box plug mentions Syracuse as being the city where home viewers sent in their drawings. Today Michael Cariglio is hosting "Inspiration Station" on Smile of a Child TV. "Pappyland" is now available on DVD. The series can be viewed on digital streaming device Roku's Family TV channel.
Pappy Drew-It (Michael Cariglio) is an artist who loves to draw, He was dressed in a hat, suspenders, glasses, a green bandana, yellow shirt, and khaki pants. The theme song suggests that he created Pappyland; although the season 5 episode "Grandpappy's Day for Drawing", which aired in 1997, suggests that Pappy's father or possibly Grandfather, Grandpappy Drew-It who was also played by Cariglio created Pappyland rather than Pappy himself. He lives in Pappyland and has many friends who live there. A running gag in the series was that whenever he coloured the picture he drew earlier in the episode he would break one of his crayons. This was done so Pappy could teach kids that you don't have to throw away a crayon just because it breaks. On occasion, when he colored in the picture, he also went outside the lines, thus teaching kids that it's all right to go outside the lines when coloring. In the original VHS, he smoked and was portrayed as a hillbilly.
Elmer (Joe Cariglio) is an old, wisecracking, and sometimes grumpy man who sits in a rocking chair in front of Pappy's desk. He tells a lot of jokes to Pappy. He also works at the Pappy Mines. At the beginning and end of mostly every episode, he would shout "Hey, sonny! Don't you know what time it is?", indicating that it was time to say hello to everyone, and that it was time to leave. He smoked a pipe in the original VHS.
Binky is a talking paintbrush who originally lived in the Brushlands, but later moved to Pappy's cabin. He likes to paint pictures.
Lily (Puppeteer Marilyn Arnone) is a talking flower who originally lived in a flower field, but later moved to a windowsill in Pappy's cabin.
Belle (Puppeteer Marilyn Arnone) is a talking telephone who lives in Pappy's cabin starting in the third season. She speaks with a southern accent and sometimes delivers news to Pappy, usually when someone is in trouble.
MailBird (Ted Long) is a bird who was introduced in the show's third season in 1995. He speaks with an English accent and delivers mail and often makes crash landings when doing so. He also works at the LetterLands Post Office. He was very disorganized, but Pappy later helped him get organized.
Sing-A-Song Sam (Michael Curley, born in Syracuse, New York) is a singer and pianist who in most episodes sang a song about the lesson learned in the episode.
Buddy Bear (Ted Long) is a bear who loves honey. He lives in a cave known as the Hamlet in Pencil Point. Like Pappy, he likes to draw, and would sometimes draw for the home viewers in situations where Pappy encountered a problem he couldn't get out of.
Chucky Woodchuckles (Puppeteer Chris Grom) is a woodchuck who lives in a wooded area in Pappyland called Woodchuckles Place. He is very friendly but tended to lose things he borrowed from others, such as Pappy's crayons. Pappy taught him about responsibility.
Tree-O are a group of three trees that lived in a forest. Their names are Oakie, Birchwood and Miss Maple. They didn't appear in later seasons, as they were replaced by Woody.
Woody is a tree that lived at the entrance of Pappyland. He once thought he had no friends, but Pappy cheered him up by drawing a picture of him. He appeared in the original VHS, and sang the song "Did you ever Wanna be". He is the only character besides Pappy, Elmer, and Grandpappy to appear in the actual show, but he didn't appear until later episodes.
Pumpkin Pop and Pumpkid are father and son pumpkins that originally lived in the Pappyland Grand Garden, but later lived on a cart next to Woody.
Turtle Lou (Gabriel Velez) is an Italian anthropomorphic turtle who lives in a grass hut by a river on the path to Pencil Point called Turtle Lou's Landing. He likes to fish. He originally appeared to look like a non-anthropomorphized regular turtle and was known as "Turtle Louie"
Doodle Bug (Puppeteer Marilyn Arnone) is a bug who was introduced in the fourth season in 1996. He tries to stump Pappy by doodling something for Pappy to finish. Pappy, however, always wins. In the Season 5 episode "The Day Pappy Forgot How to Draw", Doodle Bug stumped Pappy with a doodle for the first time. He and his Doodle family lived in the Doodle Dunes of Pappyland.
Duggan is a small parrot who appeared in a few episodes. He is usually unjustifiably angry and sometimes violent towards the other residents of Pappyland. A drawing or soothing talk from Pappy often placates him, but more often he uses it as an excuse to criticize Pappy.
Grandpappy Drew-It is a painting of either Pappy's father or grandfather and Snacker Jack's uncle. He also appeared in the original VHS.
Fur Bear was a skinny bear who lived in Pappyland in the original VHS. He spent his whole hibernation riding an elephant.
McBride was a pirate who lived in a ship in a bottle in the original VHS. He is currently searching for his pirate captain, Captain Jack.
Fishface was a mean-spirited fish that Pappy eventually won over with his kindness and drawing. He lived in the lake near Turtle Lou and did appear in later episodes.
Snacker Jack Drew-It is Pappy's city cousin and Grandpappy's nephew who appeared in the season 4 episode "Snacker Jack and the Snack Attack". At first, all he eats is junk food, but Pappy talks him into eating healthy food.
Uncle Tony is Turtle Lou's uncle who appeared in the season 6 episode "Turtle Lou visits Italy".
Donkey Dan is a donkey that lives in a stable at the barnyard.
Wanda is a woodpecker who lived at Woodchuckles Place with Chucky and only appeared in season 2 in 1993.
Songbirdy is an animated bird who appeared in season 2 in 1993.
Flutterby is an animated butterfly who appeared in season 2 in 1993.
Elizabeth Tricase is Buddy Bear's pen pal who is hearing impaired and appeared in the Season 3 episode "Pappy Talks with his Hands".
Eloise is Elmer's twin sister who appeared in two episodes of season 3 which aired in 1995.
Color Taker or C.T. for short, is a selfish bully resembling a vacuum cleaner who lived in the Color Mountain and was on the loose to eat all the colors out of Pappyland in the episode "The Day Pappyland Lost Its Color". Pappy did a drawing to show Color Taker that being a bully isn't the best way to get what he wants. Pappy then activated a switch on Color Taker to bring back the colors to Pappyland and the two became friends. Then Pappy flew in his Color-Copter to take Color Taker back to Color Mountain where he could eat all the colors he would want inside the mountain.
Santa Claus (J.P. Crangle) appeared in the Christmas special "A Pappyland Christmas".
Hans and Fritz are Santa's elves who appeared in the Christmas special "A Pappyland Christmas".