Jacob "Jake" Stonebender is a folk-musician, a regular at the original Callahan's Place as well as the brothel Lady Sally's Place, and later owner of Mary's Place and The Place. The Callahan's stories are told from his point of view. He is also known to provide live music on occasion for the bar in each of its incarnations, and is the proud owner of a custom-built guitar named Lady Macbeth.
Jake's first wife and daughter (Barbara and Jess) are killed in an automobile accident due to brake failure after Jake installs his own brakes. Jake falls into depression and is sent to Callahan's Place by Doc Webster. Jake is later informed by Mary Callahan-Finn that the brakes that failed weren't the set that Jake replaced and that he wasn't responsible for his wife and daughter's death.
Jake later marries Zoey Berkowitz and becomes the father to Erin Stonebender-Berkowitz.