Jackson entered the film industry to work on Ralph Bakshi's animated feature film Cool World. In 2001 he production designed the all-digital animated short film Los Gringos, which was critically reviewed and praised in Entertainment Weekly. He was one of several production designers on the DreamWorks production Shrek.[2] In 2023, he posted the original 1997 test animation for Shrek on his YouTube channel.[3] In 2010, he was nominated for an Annie Award for Best Production Design in an Animated Television Production for his work on Firebreather.[4]
HarperCollins released Jackson's first children's book, Danny Diamondback, in 2008.[5] The book is dedicated to his daughter Rachel. Jackson provided illustrations for the picture book Bedtime for Little Bulldozer.[6]