Saddy Dumpington
From Homestar Runner Wiki
Saddy Dumpington is Strong Sad's fantasy persona as Johnny Appleseed's right hand man. In his blog Strong Sad writes that if he 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.
