Jessica Pinkerton is a student at Greeley Elementary. She made her first appearance in "The Poor Kid", as a bully who was about to beat up Karen McCormick. Her attempts at bullying Karen were thwarted by Mysterion who severely beat her. Mysterion then declared to the rest of the school that Karen was "off-limits" before disappearing.
Jessica Pinkerton is Caucasian with long blonde hair. She wears a long, ripped orange shirt with a stretched out collar and grass-green pants.
- A woman named Nancy Pinkerton was shown to Kyle Broflovski by Abraham Lincoln in "The List". It is possible that they are related.
- One of Mr. and Mrs. Weatherhead's foster kids closely resembles Jessica, having similar hair and clothing, albeit differently colored.