Fate brings together two mismatched travelers in this comedy. Sherman (Michael Shulman) is a tightly wound, career-obsessed college student whose mother Evelyn (Donna Murphy) is a successful politician who micromanages her own life as well as that of her son. Planning to spend a few weeks in Northern California with his girlfriend Marcy (Lacey Chabert), Sherman instead discovers that she's dumped him for another, more fun-loving guy; adding insult to injury, Sherman's wallet and credit cards have been stolen and Evelyn decides it's time to cut off his allowance. With few options and eager prove he can be free-spirited and self-reliant, Sherman decides to hitch-hike to Los Angeles for an internship interview, and takes a ride with the first person willing to take him down the coast. Sherman's ride turns out to be Palmer (James LeGros), a former Olympic skiing champion turned footloose middle-aged bohemian who is more interested in keeping his vintage convertible in tune than in getting anywhere at any specific time. While Sherman and Palmer have next to nothing in common, before long the younger man finds himself learning some lessons about life from the scruffy stranger behind the wheel. Sherman's Way was the first theatrical feature from producer turned director Craig Saavedra.