Bobby Singer

In December 2011 in the episode How to Win Friends and Influence Monsters Bobby was helping Dean and Sam hunt the leviathans, led by Dick Roman (a human tycoon taken over by a leviathan). As the Winchesters made their escape in a van, Bobby ran toward it, pursued by Roman wielding a gun. Roman fired as Bobby jumped into the back of the van and it sped away. We learned later that Bobby had actually been hit -- in the head. He hung on in the hospital for a time, waking long enough to scrawl a series of number onto Sam's hand and call the boys "Idjits," and then passed away (episode Death's Door). We never learned what became of his body. We learn in the Season 7 episode "Of Grave Importance" that he "ducked" his reaper, and as such remains a ghost tied to his flask that Dean carries around.

As a ghost, he helps the boys from time to time. He still looks like he did before he died. He exhibited some signs of becoming an angry spirit where he encountered Dick Roman and shoved him into a wall (in The Girl with the Dungeons and Dragons Tattoo). Sam and Dean are worried that Bobby might become obsessed with revenge and wonder what they might need to do to help him.

. Trivia

• He had a dog named Rumsfeld (seen only once).
• He owned and ran an auto salvage yard.
• He owned a blue Ford tow-truck with South Dakota plates: 9NO3L1.
• He owned a 1971 Chevrolet Chevelle South Dokota plates: 607 82F.
• His name is an in-joke - it's the same as that of executive producer Robert Singer.
• Pattern of choice: flannel shirts.
• Head gear of choice: trucker’s hat.