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The Prof is one of the residents at the Stoolbend Mission homeless shelter who lost his tenure after sleeping with nine of his students. When Cleveland questions the content of his pipe, "The Prof" admits it isn't tobacco.

When Cleveland finds out that the homeless are getting gourmet food fixed by Stoolbend's top chefs in "'Tis the Cleveland to be Sorry", he passes himself off as homeless to get in on the goods. The shelter residents look after him after he spins a yarn about being a Vietnam vet but is caught when Donna nominates him as a Stoolbend angel for the work he claims he is doing at the shelter and is exposed on television.

After being shunned by the town, he finds the shelter residents still accept him as one of their own but that the food quality has returned back to normal after Christmas is over. Determined to raise awareness, Cleveland leads the residents back to Grundle's Department Store where they succeed.

"The Prof" is voiced by David Costabile.