In February 2006, Kress landed a small role on the popular Nickelodeon family series "Drake & Josh". He played the role of Toplin, a "geeky" kid at a birthday party with a crush on Drake and Josh's younger sister Megan Parker (played by Miranda Cosgrove) in the episode "Battle of Panthatar". Kress did not know it at the time, but this small role would lead to an opportunity that would catapult him to stardom. While filming his scenes for "Drake & Josh", television show creator and executive producer Dan Schneider took an interest in him and called him over to talk with him and to introduce him to some network executives. At the time, Schneider was developing a new series for Nickelodeon, and was on the lookout for someone to play one of the lead roles in the untitled project, which would later become known as "iCarly".