Sherman's Way (2008)

Watch Sherman's Way: An odd couple take to the open road. Having followed his girlfriend out to California's Wine Country for the summer, Yale law student Sherman finds himself dumped, and cut off from his high-society mother's money. A stranger stranded in a strange land, he hitches a ride with Palmer, a washed-up, unapologetically eccentric Olympic athlete. There are detours along the way, including the possibility of an enlightening girlfriend, an encounter with a gun-wielding gourmet chef and a chance for the former athlete to be on top again. A comedy about absent fathers and damaged sons striving to find balance between responsibility and recklessness.