Did the Pale Grin's victims really deserve their fate? On the one hand, at the end of the game it is revealed most of the victims were students and teachers that bullied and ostracized the Clown when he was a janitor. With the exception of Madison Carpenter, who he developed a crush on. John was burned alive because of a prank two jocks played on him. Said jocks could have saved him but did not because they felt he was not worth saving. On the other hand, it's implied some of them had legitimate reasons to dislike him or find him creepy. John was giving gifts to an underaged student and had a crush on her, which a fellow teacher and a few students called him out on. However, there is no evidence John did anything else, and it is possible they mostly disliked him for shallow reasons, like being a mentally unwell loner. While a few of John's victims were despicable and hard to sympathize with, it's implied that most of his victims were people he killed for disproportionate reasons, like being mean and making fun of him.
Was the Pale Grin always unstable, even as John Wade, or did his Sanity Slippage only set in after his Near-Death Experience? It's implied that he was always kind of an antisocial loner, judging by his colleagues' and the students' remarks. And then there's his borderline disturbing crush on Madison. However, there is no evidence that he was aggressive to any of his colleagues and students before the accident or that he had any plans to harm them.
Did Madison actually like John, and was she genuine when she thanked him for his gifts? Or was she just acting friendly out of fear of what he'd do if she rejected him? It should be noted that while John was bullied and ostracized by his colleagues and the students, there is no evidence that anyone feared him, meaning that it's possible that Madison was genuinely nice to him.
The Pale Grin's reaction to Madison's death implies that her Staircase Tumble truly was an accident and that for once the Clown's intention wasn't to kill. If that is the case, what did the Clown want from Madison?
Madison Carpenter's death. Madison was the only person that treated John Wade with kindness. Even when John gained a crush on Madison and started sending her gifts, it appears that she did not hold it against him and even thanked him. Then two jocks played a cruel prank on John, almost burning him alive, and he snapped, murdering all of her classmates and teachers who abused him when he was still a janitor. John eventually went after Madison and accidentally killed her. Madison treated someone who was an outcast with kindness and died for it. What sells it is how heartbroken the Clown is by her death, even writing in blood on her window, "I'm so sorry".
In John Wade's previous life, he was an outcast in his job as a janitor, being mistreated by his co-workers and the students at school. It's implied that John was both mentally unwell and friendless. He also developed a crush on a student, Madison Carpenter, that was becoming an obsession because she was the only person who treated him with kindness. One day, two jocks pulled a prank on him by lighting a fire in front of his closet door. When the fire went out of control, even though the jocks noticed that he was trapped, they chose not to save him, feeling that he was not worth saving. After narrowly surviving the experience, John snapped and went on a killing spree in his new persona the Pale Grin, murdering everyone who abused him. He also ends up killing Madison, the only person that was kind to him, much to his horror.
That One Level: Tape 11. Not only is the victim armed, his flashlight moves in irregular almost random intervals and if the light even slightly touches you you will be shot. Making matters worse is the slowed movement in the water, coupled with the fact that diving to hide from the flashlight means you can't walk. All these factors combined make the tape extremely frustrating at worst and tedious at best to complete.
