His feature film debut came in 1999 with the film Die Jungfrau (The Virgin), an Austrian film shot in Austria, Greece and Egypt that cast Kern out of New York City. He had a guest appearance on the HBO series Sex and the City followed by a role in the Broken Lizards 2001 movie Super Troopers as one of the stoners. He had a few more roles in some indie films but his career picked up a little in 2002 with the movie Cabin Fever and then in 2003 when Grind was released. At one point, he had 5 movies in post-production, including The Sasquatch Gang (released in 2007), All the Days Before Tomorrow, and One Part Sugar.