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Kress to show his interest in acting at the very age of four when he became to explore his natural talent for re-acting and memorizing the lines and shows he viewed on television.A talent agent quickly signed him with his impressive talent.
On the show, Kress plays Fredward "Freddie" Benson, the technical producer for the fictional web-show i Carly, which stars his character's two best friends, Carly Shay (Miranda Cosgrove) and Samantha "Sam" Puckett (Jennette Mc Curdy).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 M.On January 27, 2011 Cosgrove told Cleveland Live News "We're getting ready to start the next season, right after the (Dancing Crazy) tour. It's like my home away from home." While filming i Carly, Kress was tutored on the set along with his co-stars Miranda Cosgrove and Jennette Mc Curdy, and was home-schooled on the weekends or when on hiatus from the shooting of the show.I would be willing to do the show as long as people like it and as long as it works." and on February 3, 2011 Cosgrove told The Middletown Press, when speaking of the show and her co-stars, Kress and Jennette Mc Curdy: "I've known them since I was little. In the summer of 2003, before returning to his acting career, Kress and his family traveled to Lithuania with the Christian missionary organization, YWAM (Youth With A Mission), where he has given money to help people build houses for the poor.