At the age of 11, Kress was cast in the lead role as "The Emperor" in a school production of "The Emperor's New Clothes". The role rekindled his interest in performing, and at the end of his fifth grade school year, he asked his parents if he could be home-schooled so he could return to acting. A mutual friend of Kress from school put him in touch with an agent, and after attending a summer acting "boot camp", Kress was soon going on real professional auditions once again.