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.".
- Matt Angel, who portrays Jake Skinner, is the son of Dan Angel, co-creator of The Haunting Hour (TV Series)|The Haunting Hour series.
- Jake is one of the three recurring antagonists of the series, the others being Lilly D. and the Pumpkinheads.