Kern made the jump to the screen with an appearance on “Sex and the City” in 1998, playing Garth in the “Boy Girl Boy Girl” episode. Kern then landed his first starring role in the film, “The Virgin” (1999), by Austrian director Diego Donnhofer. Shot in Europe, the road drama depicts Kern as a hustling drifter who crosses the continent with his sister and his friend in search of a better life. Next for Kern was “Super Troopers” (2002), the indie comedy that was acquired by Fox Searchlight for $3 million after the 2001 Sundance Film Festival. Though he had a small roll, Kern nonetheless benefited from the movie’s success. He went on to play Tommy in “XX/XY” (2003), an independent drama about old friends dealing with new love, directed by first time helmer, Austin Chick. Kern moved on to yet another indie, “Love The Hard Way” by German director Peter Sehr, starring Adrien Brody and Pam Grier. The film won the Silver Leopard at the 2001 Locarno International Film Festival, and was also shown at the 2002 Sundance Film Festival.
Kern took a step forward in his career in the skateboarding comedy, “Grind” (2003). Playing the role of Sweet Lou, a smooth-talker more interested in sex than skating, Kern got the chance to play his first lead role in a major US release. However, the movie—a tale of four board rats trying make it on the national circuit—barely made a blip on the box office charts. But right on the heels of “Grind” was “Cabin Fever” (2003), a throwback to the old horror movies of the 70’s and 80’s. Kern played Jeff, one of five college friends who retreat to the woods for a last hoorah, but contract a flesh eating virus. The movie benefited from “Blair Witch”-like hype on the Internet, and with it, catapulted Kern into a known commodity.