He began acting at the age of 11, getting the lead role in the award winning short film entitled Chasing Daylight. He was then cast by director Mel Gibson to be 13-year-old T.J. Savage on the ABC TV series Complete Savages. After Complete Savages was cancelled, he starred in the film Saving Shiloh as Marty Preston, in the DCOMRead it and Weep as Connor Kennedy and in the film The Air I Breathe as a young Pleasure.
In 2006, Dolley appeared in Duracell's commercial "Trusted Everywhere" Campaign "Amazon". Dolley was part of the Yellow team in the second edition of the Disney Channel Games, broadcast in summer 2007. In 2008, he was in the third edition of the Disney Channel Games on the Green Team. He portrayed the rock-n-roll fanatic Newt Livingston in the Disney Channel series Cory in the House. He also stars in the Disney Channel film Minutemen, which premiered on January 25, 2008, where he played Virgil Fox. Jason played Pete in the Disney Channel movie, Hatching Pete.