From Homestar Runner Wiki
Saddy Dumpington is Strong Sad's Folk Tale World persona as Johnny Appleseed's right hand man. In Strong Sad's blog, one entry says that if Strong Sad were alive during the late 18th century, Johnny Appleseed would have to make him his best friend because "There's no way that guy had any friends". He reconsidered this situation when he realized that he'd have to do all the work and Johnny would get all the girls.
Saddy would have worn a washboard around his neck, scraping out songs like "Yankee Doodle" and "Skip to my Lou", assuming those songs were around at the time. Chances are that anything he played would sound like "SCRRREENK SCRUNK, SCRRRENK, SCRUNK" on a washboard anyway.
Strong Sad later relates the story to Coach Z. In his story, Saddy Dumpington spreads misery and woe by revealing depressing information with a smile on his face, blissfully unaware that anyone would find his news upsetting. He ends each of his stories with the phrase "Isn't that great?", as if he actually finds his depressing stories enjoyable. He also seems to think weird-looking snakes are miserable and depressing, and has a habit of naming animals "Joe".
|Strong Sad variations|
|Sickly Sam | Hot Tub | The First Decemberween | Lil' Strong Sad | Saddy Dumpington | The Deathly Pallor | Anonymous | Prancibald | 2046 Strong Sad | S. Sad|