Sherman Black (Michael Shulman) is a very privileged young man whose wealthy mother is running for the Senate. She is a domineering presence in his life telling him what to think and what career path to take for a successful life. He attends Yale and has put himself on the fast track with the aim of being a lawyer. While riding on a train with his girlfriend, she dares him to call out the next stops as a lark to prove that he is capable of being spontaneous. Naturally, it doesn't work and he stays quiet. She then asks him to come visit her in California during the summer. He declines and starts working as an intern in a New York City law office. But then, Sherman changes his mind and heads to the West Coat in a fit of spontaneity to surprise his girlfriend. She is stunned to see him and introduces him to her boyfriend. Sherman storms out and is picked up on the highway by Palmer (James LeGros), a former skier in the 1984 Olympics who is still trying to squeeze work out of his glory days (even though he didn't win a medal).

These two oddballs become friends and after Sherman loses his wallet, Palmer takes him to a trailer owned by D. J. (Enrico Colantoni), a close friend who is not only a former chef but a fine mechanic. These two men know how to relax and are not caught up in the pursuit of money, fame, and success. They introduce Sherman to the pleasures of manual labor as they all work together to restore an old MGB roadster, which Palmer intends to give to his estranged son for graduation. The New Yorker finds it difficult to handle a life with no schedules, pressure, or having to prove himself. Palmer tells him, "Time's just a loose reference." Sherman begins dating Marcy (Lacey Chabert), a clerk in a local store. Since he doesn't know how to drive or how to swim, he often feels out of place. But Palmer and D. J. do the best they can to help him stay in the present moment. Their favorite sport is fishing.

Sherman's Way is a delightful comic drama directed by Craig M. Saavedra with an appealing cast of actors and actresses. For those of us who have lived in New York City for a long time, it is hard to give up old habits and attitudes that are accepted as the only way of doing things. Palmer tells Sherman in a variety of situations to relax and take it easy. It is good advice for a smart young man who realizes that he has options other than the ones suggested by his controlling mother. Sherman gets in touch with his emotions and learns to loosen up. This movie could have been called "The Sentimental Education of Sherman Black."

Special features on the DVD include a commentary with the director and cast; deleted scenes; and behind the scenes footage.