Sherman's Way (2008)

The most captivating and hilarious odd couple in years takes to the open road in Sherman’s Way. 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, Sherman finds himself hitching a ride with Palmer, a washed-up, unapologetically eccentric Olympic athlete. The journey holds many funny and unexpected 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. This bittersweet comedy about absent fathers and damaged sons is for anyone who has ever strived to find balance between responsibility and recklessness.