"Sam...so...this is weird, huh? Look, I just wanted to say that Cass told me what you're doing for Dean. And I'm not asking you to stop, but maybe going behind his back ain't the best idea. Your brother, he can be stubborn. But I think he'd understand. And I know it's the life -- doing a little bad so you can do a lot of good. But sometimes the bad's really bad and the good -- it can come at one hell of a price. I ain't there on the ground, and whatever you do I know you'll make the right choice. You're a good man, Sam Winchester -- one of the best and I'm damn proud of you, son. I was content up here. But getting the call from you, it's the happiest I've ever been in forever, no matter what it costs. So stay safe, keep fighting, and kick it in the ass. Bobby." — Bobby to Sam in Inside Man
Robert Steven "Bobby" Singer (1950-2012) was a veteran hunter, an old friend of John, and over time evolved into a father-figure for John's sons Sam and Dean. He is also one of the longest lasting recurring characters, apart from Sam and Dean.
An alternate version of Bobby still lives on an apocalyptic Earth, where he hunts angels and demons alike.
Bobby was born in 1950. Bobby grew up in an abusive environment. His father, Ed was an alcoholic who constantly yelled at him and his mother. One day when his father was hitting his mother, Bobby pulled out a rifle and shot Ed. His father's last words stuck with him, "You break everything you touch." Years later he got married to Karen. Three days before Karen was possessed and was killed, the two had a fight about children and did not talk after.
Bobby became a hunter after he had to kill his wife Karen Singer when she was possessed by a demon. Rufus Turner is the hunter who exorcised the demon and helped cover up Karen's death. It was Rufus who introduced Bobby to the world of the supernatural, and they hunted together for many years until a hunt went wrong in Omaha around 1993. Sometime in December 1991, Sam mentions "uncle Bobby," meaning that Bobby met John Winchester and started helping him take care of Sam and Dean sometime before Christmas of 1991. He took the boys on hunting trips and even played catch with Dean in the park, as well as giving Sam the amulet that he (Sam) gave to Dean for Christmas.
While seeking Bobby's refuge from Meg and Azazel, Dean mentioned that the last time he and Sam saw Bobby (it is unknown when), he (Bobby) threatened to shoot, or "blast" Sam's and Dean's dad, John, full of rock-salt. Dean added, "You cocked the shotgun and everything" after John dropped Sam and Dean off at Bobby's house for a month without any contact, leaving Bobby to think that John had died. Following an argument with Bobby, Dean ran off to find his father, only to return with an angered John who took his sons and was chased off the property by Bobby who shot at the Impala as they drove off. Although John "just has that effect on people", Bobby was willing to help the boys get their dad back when they came to him for help, as he said, "None of that matters now. All that matters is that you get him back."
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