Jake Dillinger is the ultimate high school cool guy: handsome, popular, a star athlete from a very rich family but, has trouble reading. His parents are both criminals on the run for laundering money so he lives on his own as a teenager, leading him to distract himself with extracurriculars. He signs up for the school play for an opportunity to get closer to Christine. Jake and Rich are best friends, as shown by Rich calling him "Jakey D" and Jake affectionately calling him "his boy."