Bobby Singer (Jim Beaver), discovered a world completely different from everything he had known when his wife was possessed by a demon. Bobby's induction into the world of demon hunting came at a cost, the death of his wife at his own hands. Because of his inexperience with dealing with demons at the time of her death, Bobby began researching the supernatural world and working with other hunters. Bobby has a very close relationship with the Winchester boys, Sam (Jared Padalecki) and Dean (Jensen Ackles). He acts as a surrogate father to them fulfilling the role of his old friend John Winchester (Jeffrey Dean Morgan), who died after making a deal with a demon. Bobby assists the Winchester boys with many of their cases by providing them with supernatural information that he has amassed over the years, including spells, legends and folklore about creatures and other mythical figures.
Bobby's day job is running the Singer Salvage Yard, and he is known around Sioux Falls as the town drunk. He spends a great deal of his time in Sioux Falls and keeps in contact with the boys while they travel the countryside killing demons and other supernatural creatures. Because of the impending apocalypse, Bobby becomes demonically possessed just like his wife Karen but is able to fight the demon off and stabs himself with a knife that vanquishes demons. The demon dies but Bobby is left paralyzed in a wheelchair.
Being in a wheelchair has a serious impact on Bobby's mental and physical health, and he becomes disillusioned with his role in the fight against Satan and the apocalypse. A chance encounter with a demon, with other plans for the future, enables Bobby to once again walk and join the Winchester brothers in battle.
"She was the love of my life... how many times do I gotta kill her?"
"Don't make me get my gun, boy."
"Fat, drunk, and stupid is no way to go through life, son."