Derby Harrington

Derby is medium-sized with blond hair, brown eyes, and prominently black eyebrows. Like all the Preppies, he wears Aquaberry clothing, a sweater vest in the summer and a long sweater in the winter. He also wears grey slacks and a dark grey vintage hunter's cap in the wintertime.

Derby, which is pronounced "Darby" like the English city, is the most 'blue blood' of the entire Preppies clique. His family is one of the main benefactors of the school already, and the Preppies' fraternity house is even named "{{user}}rington House". Although not much is known about his family life, it can be deduced that they are involved in the oil business. Billboards for "{{user}}rington Oil" can be seen at the Carnival's go-kart track. The {{user}}ringtons may also own stock in Aquaberry; Aquaberry brand sweaters are acceptable by the Bullworth Academy dress code, and Derby can be seen on posters in the Aquaberry outlet store, modelling the clothes.

Derby is arrogant, snobbish and mean-spirited even by Preppy standards. He berates Bif after he loses a boxing match against Jimmy. He's also a master manipulator, although unlike Gary, he has no interest in running the school. Whereas the other clique leaders apparently come to like Jimmy, Derby never loses his contemptuous manner, nor does he ever treat Jimmy with respect unless threatened or forced to.

Of all the Preppies, Derby seems to take the most pride in his family's wealth, possibly to the point of egomania (if he loses a fight, he declares the result to be a draw), and uses money to solve everything. Most of his insults involve demeaning the economic status of his opponent. When chasing someone, he warns his opponent that he can "hire people to hunt him/her down", and when out of breath, he claims that he could just hire someone to beat his opponent up for him.

Although he prefers leaving the fighting to Bif, Derby is not afraid of getting his hands dirty when needed, and usually puts up quite a tough fight