An (only slightly outlandish) Over The Garden Wall theory
*If it wasn’t clear, spoilers for Over the Garden Wall.*
We know very little about Wirt’s dad. All we know is that Wirt’s mom remarried, had Greg with another man, and Wirt does not have a great relationship with his stepdad. It could be that Wirt’s mom divorced her husband, but it’s also possible that he passed away. If he did, that would have drastically affected Wirt’s views on life and death, which would have influenced his decisions and emotions while in the unknown. (I should clarify that I view the Unknown as some sort of purgatory/grey area between life and death. Those in the Unknown are not ready to move on to the next stage of the afterlife, whatever that may be.) But let’s take this theory one step further: what if Wirt’s dad is one of the spirits we meet in the Unknown?
In order for this to be true, we need to assume that some people’s appearances and personalities change slightly when they enter the unknown. I don’t think this is an unreasonable assumption. Take Miss Langtree, for example. I doubt that when she was alive she had a fixation on teaching animals the alphabet. It seems like your perception of reality changes when you’re a resident of the Unknown for long enough. I don’t think the residents of the Unknown know that they are dead (or something close to it). We also have to assume that their appearances change as well, or else Wirt would have instantly recognized his dad if he saw him.
Let’s go back Miss Langtree. Assuming that she didn’t actually run an animal school when she was alive, then I think that the animal school is representative of some conflict that she did have as a living person. I’m thinking something along the lines of she spent her whole life trying to help children and was unable to connect with them to provide help, which tormented her. But I’m not here to talk about Langtree, I just wanted to demonstrate how one’s struggles in the unknown could be representative of their unresolved conflicts they had when they died.
Here’s my theory: The Woodsman is actually Wirt’s dad, and his struggles with his daughter are supposed to represent his emotional conflict over dying and leaving Wirt.
If Wirt’s dad died unexpectedly, as I think he did, he would have left behind his wife and young son. He knew that his death would have a huge negative impact on Wirt, something he would struggle with for years, and Wirt’s Dad felt guilty and scared to leave his son alone. His spirit ended up in the Unknown because he’s not ready to move on; he feels guilty over his own death and feels like he needs to do more for son than he was able to.
His conflict is represented in the unknown through the Woodsman’s daughter. The Woodsman never gets to see his daughter, yet he spends every hour of every day working to provide for her, to keep her lantern lit so that her spirit can stay alive. This is Wirt’s dad (subconsciously) attempting to make up for the damage he thinks that he caused Wirt. When OTGW reaches its conclusion, both Wirt and the Woodsman reach a sort of peace. The Woodsman realizes that he can’t continue to slave away for his daughter, which is supposed to be Wirt’s dad realizing he can’t continue to dwell on what his death did to Wirt and what he could have done for Wirt if he didn’t die. Finally at peace with himself, the Woodsman, aka Wirt’s dad, is able to move on from the Unknown.
Is this theory a stretch? Oh, it’s a huge stretch. But Over The Garden Wall is a show that ends with so much still unexplained that I really think anything is possible. Besides, even if the Woodsman is just the Woodsman and nothing more, Wirt’s dad’s death would have impacted Wirt’s decisions in the Unknown. I think it’s an interesting idea to think and theorize about.