|Family|| Cliff Studebaker|
|Best Friends||Doug Funnie, Skeeter Valentine, Patti Mayonnaise, Beebe Bluff|
A friend of virtually every student at Bluffington School, Chalky is a good-natured and all-around talented student, and strives to be the best at everything he can be. Chalky lives at home with his father, Mr. Studebaker, a man whose wise advice has ensured the success of all of Chalky's endeavors thus far. But secretly, Chalky is trapped within in the shadow of his older unseen brother, Cliff, who has amassed and bettered all of Chalky's achievements in life. Chalky happens to be Doug Funnie's friend.
Chalky's sibling inferiority complex finally came to a head when his scheduled football practice interfered with his studies, forcing him to copy the answers from Doug. Doug was, of course, immediately cited as the plagiarizer by the school faculty since no one would ever think Chalky would cheat, and is told he will have to re-sit a more difficult test. To clear his name and avoid studying, Doug attempts to hunt down Chalky and question him about the incident. This proves difficult, and Doug realizes Chalky is avoiding him because of his guilt. Eventually tracking him to his house, Chalky desperately attempts to convince Doug to take the blame, citing all the times he had helped Doug in the past. Doug reluctantly agrees, and after an encounter with Mr. Studebaker, Doug learns of Chalky's secret war with his brother and forgives him. Doug convinces Chalky to retake the test and admit to his father why he cheated. Chalky sits out during the football game to make up the test.