Ricky Dean (HUEY LEWIS) is a Karaoke hustler who travels from one small-town contest to the next, fooling aspiring crooners into betting against his vocal abilities and then taking their money and leaving for his next spot before his victims know what happened. Slick and carefree, Ricky runs into an unforeseen complication when he meets Liv (GWYNETH PALTROW), the adult daughter and Vegas showgirl he never knew he had, at her mother's funeral.
Todd Woods (PAUL GIAMATTI) is a traveling salesman who's become fed up with his profession, his life and society in general. When he returns home and his wife, Candy (KIERSTEIN WARREN), and their kids essentially ignore him, he goes out for a pack of cigarettes and doesn't return. As he aimlessly makes his way across the country, he picks up Reggie Kane (ANDRE BRAUGHER), an amiable, but armed and escaped convict with a great voice.
Billy Hannon (SCOTT SPEEDMAN) is a cabbie who's just caught his wife/girlfriend Arlene (ANGELINA PHILLIPS) cheating on him with his partner after being berated for being a loser by his former third grade teacher (MARIAN SELDES). When he later meets Suzi Loomis (MARIA BELLO), a brazen, aspiring singer who's desperate to get to Los Angeles, he decides to give her a ride.
As the three, disparate pairings of twosomes make their way across the country eventually qualifying for and then heading to a $5,000 Karaoke championship in Omaha, Nebraska, they learn profound things about themselves and each other.