Schilling's screen acting debut was in 1996, when he, aged 14, appeared in the Sat.1 TV series ‘Hallo, Onkel Doc!’ He was later cast in the theatrical film Schlaraffenland (1999) where he played alongside Franka Potente, Daniel Brühl and Heiner Lauterbach, but the breakthrough for him came with his performance in Crazy (2000, directed by Hans-Christian Schmid), for which he received the Talented Young Actor Award of the Bayerischer Filmpreis.