As Grampa drives Homer’s car down a roadway, he clips another vehicle and loses control. Homer’s car flips over, and tumbles down an embankment. As Grampa babbles, Homer closes his father’s nose with his fingers. It turns out to be a dream. In reality Homer is driving Lisa to town hall, where Lisa delivers Girl Scout-type cookies to Mayor Quimby. The Mayor can’t pay for the cookies because, as it turns out, the town of Springfield is broke. During a city hall budget meeting, Quimby breaks the news to a crowd of onlookers. Homer makes a suggestion: the town should fake a disaster to bilk money out of the federal government. Quimby informs a FEMA official that a hurricane rolled through town. The FEMA official approves ten million dollars in emergency funds in exchange for a $2500 processing fee. It turns out the FEMA official is a scam artist. Lisa goes through the city’s financial records, and discovers the town is owed millions of dollars in uncollected taxes. In a short period of time, the city coffers are flush. Only one person’s back taxes remain unpaid: those of country music star Lurleen Lumpkin. Lisa reminds Homer that he once managed Lurleen’s singing career under the pseudonym “Colonel Homer.” Kent Brockman announces that she owes Springfield twelve million dollars. People throughout town begin searching for the missing Lurleen. Homer believes that Lurleen is long gone… until she turns up in the back of his car. Homer tells Lurleen she can stay with his family, but Marge nixes the idea, believing she will make a play for Homer. Marge drives Lurleen to a seedy neighborhood, and attempts to abandon her, but has a change of heart when she fears for Lurleen’s safety.

Marge allows Lurleen to stay with the family, but Chief Wiggum takes Lurleen into custody. A judge orders her to pay off her debt a little at a time. Afterward Lurleen gets a waitress job at Moe’s tavern. One night in the Simpsons’ basement Lurleen pours out her heart in song. The family hears the song, and realizes that Lurleen is heartsick over the absence of her deadbeat father. Marge decides to take action. She tracks down Lurleen’s father Royce, and tells him about Lurleen’s feelings. Royce and Lurleen are reunited, and Lurleen’s outpouring of love makes Homer jealous. After Lurleen writes a song to express her feelings, Royce sneaks off into the night, leaving Lurleen behind.

One morning Lurleen hears the Dixie Chicks singing her song on the radio. Lurleen realizes her father has betrayed her. Homer dons his “Colonel Homer” outfit. Marge, dressed in a skimpy Calamity Jane outfit, creates her own persona: “Major Marge.” Marge urges Lurleen to stop getting self-esteem from the men in her life. Inspired, Lurleen marches down to a recording studio, confronts her father, and smashes a guitar over his head. When the Dixie Chicks realize Royce stole their song from Lurleen, they advance on him. Later, Lurleen thanks the Dixie Chicks for allowing her to open for them… and she falls in love with a biker who looks a lot like Homer.