How Bobby Singer Appeared on the Winchesters
In Supernatural, Bobby Singer is the father figure to Sam and Dean, and he may appear in The Winchesters.
Bobby Singer is one of the most beloved characters in Supernatural, and his decades-long friendship with John Winchester made him the perfect man to appear in its prequel series, The Winchesters. The inclusion of Bobby may require some work with the Supernatural canon to help his appearance make sense. However, the satisfying rewards will greatly outweigh the effort required.
Where John Winchester failed as a parent in Supernatural, Bobby Singer stepped up. Rough Hunter isn't the perfect father figure, but he puts in the work where it counts, and Sam and Dean respect him for it. He watches over and guides young Sam and Dean while John is missing, guiding them in their time of need and providing them with a home when they never had a real home before. He even ends up sacrificing his life to fight alongside them. There is no supernatural character more deserving of an appearance than the Winchesters.
Bobby Singer In The Winchesters Is Tricky
As with most of the timeline in The Winchesters, Bobby's presence is tricky. In Supernatural, Bobby enters the hunting world after his wife is possessed by a demon and he is forced to kill her. Bobby and John weren't friends until Sam and Dean became friends young boy while John had been heavily involved in the hunting life sometime in the early 90's.
The Winchesters are set in the early 1970s, and Bobby's appearance may not coincide with the Winchesters' timeline. Flashbacks of Bobby Singer's early hunting days also show him looking older than other 20-something hunters around the time of The Winchesters. Unless it's a brief Easter egg cameo in a scene set before John and Bobby know each other, it's hard to include it in the canon.
Why Bobby Can Still Appear In The Winchesters
While Bobby's presence would be tricky, it's not impossible. Much of the original supernatural canon has been altered to suit the needs of the Winchester family, so a Bobby appearance isn't entirely out of the realm of possibility. In The Winchesters, John was involved in game hunting much earlier than the original Supernatural timeline would suggest. This major change allows for greater fluidity in dates. Appearing older in flashbacks isn't much of a problem either, since Tom Welling already appears as a version of Samuel that looks older than the canon would suggest, which invalidates this rebuttal.
with While theories abound about the Winchesters taking place in their own universe, Bobby's appearance in the Supernatural prequels is still a possibility. There is a long history between John and Bobby that has never been explored in detail, and the Winchesters present the perfect opportunity. Although the two eventually fell out, their friendship was once strong enough to create a family through Sam and Dean. With modifications to the Supernatural timeline, a young Bobby Singer could make a well-deserved appearance in the Winchesters.