I like my Laughing Jack to be a truly empty, demonic husk of what he once was.
Thereās a good reason everyone in the Forest stays far, far away from him. Laughing Jack is among the most cruel and sadistic of any entity in the Forest. If approached, he will torment the person for however long it takes him to get bored again. If provoked, he will haunt, torment, and kill his the person. The reason he attacks is because he doesnāt not like to be reminded that he exists.
This Jack has such a deep sorrow and emptiness inside of him, that heās tried to destroy himself time and time again to no avail. He is not human, not made of earthly flesh. He will not ādieā, unless the box from which he came is burned to ash and the ash is sealed away. Even death for him is just finding a new vessel, a new Jack-In-The-Box, meaning the cycle could repeat.
Laughing Jack often visits Dove in her dreams, begging for her to take mercy on him and find a way to kill him so he can stop the anguish of existing so far from your purpose. She has no access to his box, nobody knows where it would be. The box remains in the attic of Issac Grossmanās home. The house didnāt change much throughout history and the quiet, dark, cobwebbed corner of the attic remained ignored.
Jack has an intrinsic connection to the box, but has severe memory loss. He doesnāt remember where he came from, what he was meant to be, how he exists, he doesnāt remember Issac. All he can feel is the need to bring suffering wherever he goes.
(His knees have worn down to the bone from kneeling for literal years, praying to be taken from this plane of existence)
This version of Jack is a read on what an unintegrated, bottled up shadow looks like in psychology. When you donāt understand yourself, you begin to hate yourself, in that hate you lose your compassion and begin to destroy yourself. This is what Jack has done.