For a long time it has been uncertain exactly what the purpose of “the pills” is. Let’s do a walkthrough of them, shall we?
The pills first show up in Entry 16. Jay is snooping around in Alex’s house. In this Entry, Jay discovers a water bottle, a bullet casing, drawings, and the bottle of pills beside a bloodstained sink.
Entry 19.5, Jay is reviewing the things he took from the house, including the bottle of pills. But now, the pill bottle is empty and he has no recollection of taking any.
Entry 20, Tim has a coughing fit and takes some pills, identified as the same, if not similar pills, to the ones Jay swiped. Jay states he does not remember the events of this entry happening.
Entry 23, Jay returns to the house and is attacked by Masky. An open bottle of pills is sighted on a sidetable.
Entry 28, Having no knowledge of where he is or how he got there, Jay searches his hotel room and finds a bottle of pills.
Entry 61, perhaps the biggest insight into the nature of the pills. Hoody breaks in to Tim’s house, takes his pills, and as Tim starts to cough violently, he is unable to find his pills and has a seizure. Afterwards, he takes his trademark jacket and leaves.
Entry 73, Hoody goes on a search for pills, showing us that his inventory has dwindled to a measly single pill.
Entry 74, Jay refuses to take any more of Tim’s pills, which Tim has been sharing with him because he believes they are going to “help him.”
It would seem that the pills ward off the effects of The Operator, or the so-called “Slender-Sickness”. If Tim goes without his pills, he becomes Masky. So why is it that Hoody continues taking the pills? This would imply that Hoody is no one’s alter-ego, as Masky is to Tim. Hoody is someone in complete possession of their mental faculties. However, this person is in cohorts with Tim’s alter-ego, Masky, but not Tim himself. This might imply that Hoody is no one we have met yet from the series.
However, one thing that bothers me the most: Hoody feels as though they need the pills. Entry 73 is a testament to that. So why is it he has allowed his stores to fizzle out to one single pill? Why has he not gone out for more? Or perhaps he has, but has been unable to access more? He knows that Tim has the pills, but instead of stealing them, he lets him keep the few pills he has. This could be evidence to the (increasingly unlikely) theory that Hoody is Jay from the future. Hoody wants his former self to take the pills, perhaps to prevent things from occurring.