In 2008, Kress starred in the Nickelodeon television movie '. In the movie, Kress played "Roland", a decidedly uncoordinated student who transfers to a new school and must be whipped into shape by his ambitious gym teacher, Dave Stewie (Christopher Meloni). Later that same year, he starred as Freddie Benson in the television movie ', Nickelodeon's first television film adaptation of "iCarly" television series. Throughout 2009, Kress continued to play the role of Freddie on "iCarly", but was unable to take on other projects due to Nickelodeon's decision to film both seasons two and three of the show back-to-back without the usual hiatus between filming seasons, in order to make up for the time lost during the 2008 writers strike.