When Kress was young, he would quote lines and monologues from television and perform for his family and friends. He began modeling, acting and voiceover work at 3 years old. At age 6, he took a break from acting, and at about age 10, asked his mom to begin homeschooling him so that he could pursue acting again. He voiced the role of Eizan Kaburagi from Nickelodeon's animated series, Shuriken School. He has also guest starred in The Suite Life of Zack and Cody as Jamie. Kress has enjoyed playing dramatic roles in "House", "Standoff", and "Without a Trace".