Deputy Bob is a story about Timmy O'Brien's journey to accept a place in his father's legacy, learning about his own identity during the process, and Professor Smith's misfortunes encountered while seeking approval from others. Intricately woven, both stories run parallel in current time and through remembrances of the past, while taking place on separate sides of the country. The common link is Dr. O'Brien, Timmy's father as well as Smith's boss, and his noble research into a radical cure for cancer. While mainly comedic, the story is also told with dramatic and surreal moments.