Recurring / Guest stars:
- George Ball as Derek Malone (unseen)
- Deborah Shelton as Debbie
Sam's brother, Derek (an unseen character, voiced by George Ball), who exceeds Sam in: success, education, talent, and looks, arrives in Boston via his private jet. Derek entertains bar patrons with his talents. He teaches Coach to speak Spanish for a coaching job in Venezuela and offers Norm a job. Derek and Diane begin dating, making Sam jealous.