In New York City, Jake Ferris is a popular country and western singer at the Rhinestone club. Leaving the stage after a performance, she fends off flirtations from her lecherous business manager, Freddie Ugo, and longs to terminate her contract with him. When she argues that he is incapable of discovering and developing talent, while claiming she can turn any person into a “Rhinestone cowboy,” Freddie makes a wager with her. He will release Jake from the three years left on her contract, if she can turn an average person into a singer who can perform one song without being heckled by the Rhinestone’s tough audience. Freddie will select the person and Jake will have two weeks to complete the transformation. However, if her protégé fails, Jake’s contract will remain valid, with an additional five year option. When Freddie adds that she must also spend a night with him if she loses, Jake balks, but finally accepts the bet. Outside the club, Freddie tries to select a homeless man, as Jake protests. She agrees to take the next “normal person” who comes along. Suddenly, Nick Martinelli, a boisterous taxicab driver, pulls up to drop off a group of Japanese tourists. At first, Nick is not interested in a wager involving “hillbilly” music, but after he is fired for wrecking the taxicab, he negotiates with Freddie for a new vehicle if Jake wins her bet. Anxious to get started, Jake asks if Nick can play any musical instruments and he takes her to his father’s funeral home where he plays a few notes on the organ and performs a poor imitation of rock and roll singer, Chuck Berry. Nick’s Italian-American parents doubt their immature son will succeed in this endeavor, but Jake strongly disagrees and plans to immerse Nick in country music by taking him to her hometown, Leipers Fork, Tennessee. After arriving, Jake has Nick perform with her father, Noah Ferris, and his bluegrass band, the Wild Possums. Nick’s wild gyrations and singing scare not only the locals, but also the farm animals. When Noah privately asks if she and Nick are romantically involved, Jake immediately dismisses the idea. To begin the transformation, Jake teaches Nick about living on a farm and and acting like a cowboy. After awhile, Nick becomes weary of Jake’s nagging and needs a break. At the Cut n’ Slice, a local bar, he meets country singer Barnett Kale, and enjoys partying with him. The next day, Jake becomes furious that Nick was carousing with Barnett, her former boyfriend, whom she calls a liar and cheater. As they reach an understanding, she promises to make the lessons more, “fun,” and Nick agrees to work harder. While slow dancing later at the Cut n’ Slice, Nick admits to Jake that he is becoming fond of her and refuses to let her ex-boyfriend cut in. Barnett punches Nick in the face and waits for him to fight back, but Jake convinces Nick to walk away. Jake is encouraged by Nick’s progress as they sing on the porch that evening. They nearly kiss, but Noah interrupts them. In preparation for Nick’s appearance at the Rhinestone, Jake introduces him as “Howlin’ Nick Martinelli” to the audience at the Cut n’ Slice. At first, Nick is too nervous to go on stage, but Jake encourages him. After Nick subdues Barnett and the other hecklers with a few jokes, he performs a rousing duet with Jake, and the crowd cheers. That night, Nick and Jake make love. Back in New York City, Nick shows off his cowboy clothes, as his parents host a party for him and Jake at an Italian restaurant. Mr. and Mrs. Martinelli are proud of their son’s commitment to becoming a country singer and toast him as “Hopalong Meatball.” When Nick announces to everyone that he is a singer now and no longer wants to drive a taxi, Jake is surprised and reminds him that she trained him to perform just one song, while an actual career on stage will take more than two weeks. In front of the crowd, she calls him a “robot, for now,” and Nick is embarrassed. As they bicker, Jake blurts out that she should forget the wager and give in to sleeping with Freddie. Unaware that sex with Freddie was part of the bet, Nick is furious. The argument escalates into a shouting match, and Jake walks out of the restaurant. Later, a waitress at the Rhinestone warns her that Freddie has arranged for hecklers to attend Nick’s debut, but Jake is not concerned, as she feels disheartened about her behavior at the restaurant and is prepared to forfeit the bet. On the night of his Rhinestone performance, Nick nervously waits backstage. Meanwhile, Jake is at Freddie’s apartment ready to concede defeat, and Freddie pours champagne to begin their night together. As soon as Nick learns Jake’s whereabouts from the waitress, he rushes out of the club to rescue her. Unable to hail a taxi, Nick borrows the horse of the Rhinestone’s cowboy doorman and gallops into the lobby of Freddie’s apartment building. He bursts through the front door the moment that Jake punches Freddie, indicating she does not need rescuing. Tired of never finishing anything, Nick convinces Jake to follow through with the wager. Although he wants to perform a duet with her, Jake says he must win over the audience on his own to secure the bet. When Nick takes the stage, his attempt to tell jokes and sing a country song elicits jeers from the crowd. Cutting the tune short, he switches to a sexy banter that suits his personality and performs an energetic country rock tune. The crowd becomes enthusiastic and claps along to the music. As Jake joins Nick on stage, Freddie watches the cheering audience and realizes he has lost the bet.