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 (so called because it used to 'stab him in the back' constantly until he learned how to play her properly).
Jake's first wife and daughter (Barbara and Jess) were killed in an automobile accident due to brake failure; Jake had just installed his own brakes and offered to take his family for a ride. After the crash, Jake fell into depression and was sent to Callahan's Place by Doc Webster. Years later, Jake was 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 is attracted to heavier women and was briefly Mary's lover before she met and fell in love with Mickey Finn just hours later. He continued to carry a torch for her afterward, even naming Mary's Place in her honor, before he finally met and married the bass player Zoey Berkowitz. The two are the parents of Erin Stonebender-Berkowitz.
His good humor, musical gifts and intuition in a crisis have saved the day more than once, and no less than Callahan himself, Jake is part of the Place's heart. "Even in the times you were down," Long-Drink McGonnigle once told him, "you were always the merriest of us, Jake."