|Family|| Cliff Studebaker|
|Best Friends||Doug Funnie, Skeeter Valentine, Patti Mayonnaise, Beebe Bluff|
A popular student at Bluffington School, Chalky is a good-natured and all-around talented individual, who 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'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 believed that Chalky would cheat, and is told that he will have to take a more difficult re-test. In order to clear his name and avoid having to take the re-test, Doug attempts to hunt down Chalky and question him about the incident. This proves difficult, and Doug realizes that 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. While Mr. Studebaker is bragging to Doug about his son's achievements, a visibly annoyed Doug mumbles to himself that Chalky is a cheater. However, Mr. Studebaker overhears this comment and questions him about it, which causes Chalky to confess. Chalky eventually agrees to re-take the test, and sits out during the football game to do it.