- Played by Jim Beaver.
- Appears in: 1.22 Devil's Trap, 2.01 In My Time of Dying, 2.14 Born Under a Bad Sign
- Bobby owns Singer Salvage Yard (also seen written as Singer Auto Self Service Salvage Yard, on a sign in Everybody Loves a Clown,) and lives in a house on the premises. His exact location is not given.
- Owns a blue Ford tow-truck with South Dakota plates : 9NO3L1.
- Gathering from the wealth of books in his house and his dialogue and role in Devil's Trap, is somewhat of a demonology expert.
- His dog is called Rumsfeld, a reference to the US Secretary of Defense, Donald Rumsfeld.
- John Winchester and Bobby are not necessarily on good terms (Dean comments that the last time Bobby saw John he nearly "filled him with buckshot").
- The name 'Bobby Singer' is a reference to Supernatural's executive producer, Robert Singer.