Despite being avidly against bullying, he consistently bullied several people at South Park Elementary, including Mr. Mackey, Stan Marsh, Lorraine, and all of the students that attended the anti-bullying assembly. He bullied Stan in the bathrooms when he learned that Stan sold the video rights to Nick Jabs. The producer was able to keep Bailey from claiming credit for the movie by threat of a lawsuit. This caused Bailey to cry because he believed that the profits from the movie would have made Bucky Bailey's Bully Buckers a national organization.
Bailey wears a red sweater-vest with a yellow diamond pattern on it. He also wears a white shirt with a black tie, khaki pants, a black belt, and brown shoes. He is overweight, has a brown mustache, and has a Captain Kangaroo-style haircut.