Founding members Gunnar Madsen and Matthew Stull decided to form an a cappella group when they left their jobs as deliverers of singing telegrams in San Francisco. Instead of singing more traditional doo-wop songs, The Bobs started out with original arrangements of their own songs and songs like "Helter Skelter" and "Psycho Killer". Although two of their albums are dominated by songs written by others, the overwhelming majority of their repertoire is original, with songs discussing a diverse array of humorous subjects.