Dolley gained his first stage experience at 11 when he and one of his brothers performed the Abbott and Costello "Who's on First" routine in a school talent show. His first real acting jobs came that same year. He won 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 Disney Channel Original Movie Read it and Weep as Connor Kennedy and in the film The Air I Breathe as the younger form of the character named 'Pleasure' (the adult version of whom was played by Brendan Fraser).
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 mid-2007. From 2007 to 2008, Dolley starred in the Disney Channel show, Cory in the House. In 2008, he appeared in the film Minutemen as Virgil Fox and was in the third edition of the Disney Channel Games on the Green Team. In 2009, Jason starred in the Disney film Hatching Pete as Pete Ivey. In 2010, Dolley began appearing in his second Disney Channel Original Series, Good Luck Charlie as P.J. Duncan.
When asked about his role in the new Disney Channel Original Series family sitcom, Good Luck Charlie, he replied, "I like the realness of it. I like the more authentic tone. I like the family sitcom. That's something different for Disney, which also appealed to me." He also said in a different interview, "When I read the script, I was like, 'Oh, this is kind of cool. This is a little different. It has a Full House kind of feel. It's very family-friendly. Families can sit down and watch this and get a real laugh. I think that's what's been cool about it from the start and what's still cool about it today."
Dolley and cast appeared be in a feature-length Christmas Disney Channel Original Movie based on the series entitled Good Luck Charlie, It's Christmas! began production in March 16th 2011 for a December 2011 premiere. He also appeared on Disney Channel's Tinker Bell and the Pixie Hollow Games, an animated movie which also stars Brenda Song, Tiffany Thornton and Zendaya.
Dolley produced his first film in 2011. Dolley is working on a new film which stars Zac Efron.
His favorite things to do include guitar, piano, video games and paintball, he also enjoys playing football with his friends. He likes to spend time with his pet chocolate Labrador retriever and his family as well as staying active in his church youth group. Dolley currently lives with his parents in Simi Valley, California. When not filming he takes college courses in philosophy at Moorpark College.