Jake was once a loner in 1961. He kept getting bullied by some jocks. So he then, pulled a prank on them. Unfortunately, his tormentors got even on the night of the school dance. The jocks locked Jake in a cage, which then they burned the gym to the ground. Everyone made it out alive, except Jake.
In the present, Jake helped Will with his bully problem and Will would return the favor. During a class trip, he pretended to be a dead body in front of Travis and Chang and sat up screaming causing them to run. He helped Will, but decided to kick it up a notch (which Will allowed). However, Jake ended up giving the bullies panic attacks. When Will found out that Jake was a ghost Jake told Will couldn't back out because he owed him. Jake sent Will back in time to the day he died. Jake was rescued, but left Will to die. Since he didn't die, Jake began life anew. Jake went to the dance and introduced himself to Anna [Will tried to warn her]. As the two shared a dance, Jake noticed Will and said "Now we're even.".
Jake is haunted by an angry Will after that point, but this does not bother him as he was himself a ghost for fifty years. Jake's cockiness and smugness about his new life ends abruptly when the Grim Reaper appears before him at his house, calling Jake a liar, a thief, and an abomination. The Reaper puts a curse on Jake so that his body slowly rots into nothing, but Jake comes up with a plan: trick Anna into giving up her life just like he tricked Will. During a date with Anna in the woods, Jake explains the situation to Anna (by the right half of his face rotting away), but she is horrified by him and wants to be taken home. He berates her, calling her shallow, which almost causes her to agree to the deal by shaking Jake's hand. This is interrupted by Will, who has found the power to fully materialize out of his love and protective instincts for Anna. Jake and Will fight, but Jake loses when Anna hits him in the ribs with a tree branch. At that point, the Grim Reaper reappears and drags a screaming Jake to the underworld for his crimes. After Will and Anna leave the woods, the former being granted his life back by an angel, Jake's hand comes up out of the ground to grab his comb.