In April 2005, Kress made his first live television appearance since returning to acting in a comedy sketch on "Jimmy Kimmel Live!" where he played a young Simon Cowell of "American Idol", and would continue to appear in various comedy sketches on the show a total of 5 times over the next year. Kress continued to land steady work over the next two years, appearing in guest-starring roles on dramatic series such as "House", "Standoff", and "Without a Trace" as well as the Disney Channel comedy series "The Suite Life of Zack & Cody". Kress also appeared in several short films including "Pickled", "Magnus, Inc.", and "Bag", for which he was awarded a 168 Film Festival Jury Award for his portrayal of a small-fry drug dealer with a conscience. In addition to live-action roles, Kress continued to work as a voice-actor, lending his voice to various characters in the animated feature film "Chicken Little" and on the Nickelodeon animated series "Shuriken School".