Here's where the story gets deep. (This project is dark) Both of the segments take place in the past. the first segment is when Ollie was a kid and his family was offed by SAM. He goes to the bridge where he and his family used to fish, and looked into the sky and shouted, "DARN YOU, DARN YOU, YOU STUPID RED PIECE OF POOP!" He started sobbing. Years later, before the song All Circles, he visited the bridge to think about things, like if he should off himself to be with his family, but Tanner's ghost found him and caught him talking to himself about "it". He started talking to him to no avail... Ollie made up his mind. If he was gonna die he was gonna die in honor, and that is why he jumped in front of the spike at the end of all circles.
PS, the reason why tanner's voice is so high pitched is because he died as a kid. Another thing is SAM shot his mom, threw his dad at a wall, breaking his skull, and crushed Tanner's head with his bare hands.