Kress was born on November 18, 1992 in Glendale, California. He has two brothers, Andrew and Kevin, neither of whom are involved in show business. Kress began his professional career at the age of four when he displayed a natural talent for memorizing and re-enacting the shows he saw on television, prompting his mother to take him to an open "cattle call" showcase where he was quickly signed with a talent agent. 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. At the age of six, he decided to take a break from acting and return to regular school, where he led a relatively "normal" life for the next five years until deciding to return to acting professionally at the age of eleven.