Tras perder seres muy queridos, Walter (Ashton Kutcher) y Linda (Michelle Pfeiffer) intentan seguir adelante con sus vidas. Por un lado, Walter es un joven luchador profesional que regresa al hogar familiar después del brutal asesinato de su hermana, días antes de su boda. Por otro, Linda es la madre de un niño sordo cuyo marido alcohólico ha muerto a manos de un amigo en un bar. Mientras tienen lugar los juicios por ambos crímenes, Walter y Linda tienen una aventura amorosa.

On Broadway tells the story of Jack O'Toole, a 30-something Boston everyman, who writes a play about his dead uncle as a way to reconnect with his hard-nosed dad. With no money and just his gut to guide him, Jack quits his job as a carpenter so that he can mount a production of his play on the only stage he can afford: in the back room of his neighborhood pub, on a little street called Broadway.

Finding his only escape in music, Gil Blackwell (Josh Hamilton) decides to leave his monotonous business life in Boston when his cousin dies in a car accident. Gil ignores his father's disapproval and takes the family's antique truck for the promised land of California, but on the way a chance encounter reunites him with an old college flame, Genevieve (Fried Green Tomatoes' Mary Stuart Masterson), who joins his journey.