In 1995, he graduated from St. Xavier High School in Cincinnati, and subsequently studied at New York University, earning his Bachelor of Fine Arts (BFA) in drama.
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.
At one point, he had 5 movies in post-production, including The Sasquatch Gang (released in 2007), All the Days Before Tomorrow, and Just Add Water (2008).
In 2016, Kern was cast in a recurring role on TNT's new drama series Good Behavior, starring Michelle Dockery, which ran two seasons.
[5] In 2017, Kern wrote, directed, and starred in Big Bear, which is based on his broken engagement to actress Ginnifer Goodwin.