In Supernatural, Bobby Singer serves as a father figure for Sam and Dean, and he could potentially make an appearance in The Winchesters.
Bobby Singer is one of the most beloved characters in Supernatural, and his decades-long friendship with John Winchester makes him a perfect candidate to appear in its prequel series, The Winchesters. Bobby’s inclusion may take a little work with the Supernatural canon to help his appearance make sense. However, the satisfying payoff would heavily outweigh the effort required.
Where John Winchester fails as a parent in Supernatural, Bobby Singer steps up. The gruff hunter isn’t a perfect father figure, but he puts in the effort where it counts, and Sam and Dean respect him for it. He watches over and mentors a young Sam and Dean when John disappears, guides them when they need it, and provides them with a home when they’d never had a real one before. He even ends up sacrificing his life fighting alongside them. There is no Supernatural character more deserving of a The Winchesters appearance.
Bobby Singer In The Winchesters Is Tricky
Like much of the timeline in The Winchesters, Bobby’s appearance would be tricky. In Supernatural, Bobby enters the world of hunting after his wife is possessed by a demon, and he is compelled to kill her. Bobby and John don’t become friends until Sam and Dean are young boys, and John is already heavily involved in the hunting life, sometime in the early 90s.
With The Winchesters set in the early 70s, it’s possible Bobby’s appearance may not align with The Winchesters‘ timeline. Flashbacks of Bobby Singer in his early hunting days also show him looking older than his fellow hunters, who are all in their 20s, around the time The Winchesters takes place. Unless it’s a brief Easter egg cameo in a scene set before John and Bobby know each other, it would be a difficult inclusion to justify with the canon.
Why Bobby Can Still Appear In The Winchesters
Though Bobby’s appearance would be tricky, it isn’t impossible. Much of the original Supernatural canon has already been changed to suit the needs of The Winchesters, so Bobby’s appearance isn’t entirely beyond the realms of possibility. In The Winchesters, John is in the hunting game much earlier than the original Supernatural timeline suggests. This significant change allows more fluidity when it comes to dates. Appearing older in the flashback is also not much of a problem, as Tom Welling has already appeared as a version of Samuel that looks older than the canon suggests, making this counter-argument null and void.
With theories abounding that The Winchesters is happening in its own universe, Bobby’s appearance in the Supernatural prequel is still possible. There is a long history between John and Bobby that has never been explored in detail, and The Winchesters presents the perfect opportunity. Though the two eventually have a falling out, theirs was once a friendship strong enough to build a family through Sam and Dean. With a reworking of the Supernatural timeline, a young Bobby Singer could make a well-deserved appearance in The Winchesters.
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