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Over the next three years, Kress modeled for various print advertisements, as well as performing in numerous commercials and voice-over roles; the most notable of which was his dual role as the voices of "Easy" and "Tough Pup" in the 1998 feature film Babe: Pig in the City.
Although i Carly would not premiere until the fall of 2007, the decision was made to cut Kress' scenes with Miranda Cosgrove out of the Drake & Josh episode that had started it all, in order to avoid any potential confusion among the young Nickelodeon viewing audience.
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.
Kress told of his CSI role "It was a great opportunity to try my hand at something different.
I had done scenes in dramas in the past, but other than a few semi-serious scenes on i Carly, it had been a long time since I've had the opportunity to do anything other than comedy." Later that same year, Kress returned to comedic roles, guest-starring as Prince Gabriel on the Nickelodeon comedy series True Jackson, VP, and as the voice of Ronald on the Nickelodeon animated series The Penguins of Madagascar.