|Relatives:|| Mr. Osgood (father)|
Mrs. Osgood (mother)
|Voiced by:||Richard Horvitz|
Jimmy Osgood was a student at Dakota Union High School.
Jimmy was a very smart kid, but pretty much a loner. He preferred to surf around the Internet on his laptop rather than engage in social activities. He was bullied all the time by Nick Connor and his friends as a result.
Virgil and Richie started hanging out with him, and as a result, he rose somewhat on the popularity scale. Frieda asked him to help on the Dakota Fright Fest, which he gladly accepted. He turned out to be the greatest help they could've wished for: with his creativity, he made scarier (and even better) decorations than the years before.
Nick, in the meantime, tried to make his move on Frieda. When he caught Jimmy (accidentally) eavesdropping, he chased him, beat him up and stuffed him in a locker. Frightened and broken, Jimmy was helped out of the locker and then went home to pick up his father's gun, and pulled it on Nick. Richie managed to dissuade him, but as he lowered the gun, Kevin and Ray jumped him and the gun went off. Richie was shot.
The gunshot caused all outbursts to subside, and Jimmy curled up in a corner, crying.
In the end, Jimmy underwent psychological treatment and was sent for treatment at a juvenile detention center, while Nick was suspended, and forced to do community service for what he did to Jimmy; his friends received the same punishment.
After the incident, Jimmy left an effect on Virgil, who began to question himself about what he could have done to prevent Jimmy from hurting someone, and felt that Jimmy's kind does not belong to juvie.