Bart is knocked off his skateboard by Mr. Burns in his car. After a brief trip to Heaven, and a slightly less brief visit to Hell, he falls to Earth. With the help of dodgy lawyer , Homer tries to sue Burns for a million dollars. And Marge and Lisa discover there are many ways that you can arrive at the truth.
While out riding his skateboard with reckless abandon, Bart is hit by a car driven by Homer's boss, Mr. Burns. While Burns and Smithers argue about what to do about him, His soul floats out of his body and he ascends a luminous stairway to Heaven. When Bart spits over the edge, the stairway turns into a chute and sends him directly to Hell. After the Devil looks over his case history on his computer, he sees that Bart is not due to arrive in Hell for nearly another century. As he begins to regain consciousness, the Devil tells him to be rebellious and listen to heavy metal music. Bart wakes up in a hospital bed with Homer, Marge, Lisa and a strange man hovering over him. Asking the strange man, Lionel Hutz, who he is, Lionel presents Homer with his card and tells him if he wants to make a lot of money, to give him a call. Acting on his lawyers’ advice, Mr. Burns offers Homer money to ensure he does not take legal action against him. But he only offers Homer a paltry $100. He turns it down because it barely covers Bart's medical bills and calls Lionel Hutz.
After learning that Homer is going to sue him, Mr. Burns becomes furious and decides to fire him. After Smithers reminds him that firing a man who's son he hit with a car would be bad for his image, Burns has no choice but to settle the lawsuit in court or talk the Simpsons out of it.
At Hutz's office, he assures Homer that if he does exactly what he says, he can get a settlement for a million dollars (of which he gets 50% as part of his fee). But to do it, Bart has to lie about the extent of his injuries. To further stack the deck in their favor, Hutz uses the legal testimony of a shady doctor, Dr. Nick Riviera, to come up with his own diagnosis. However, Marge is suspicious of his medical qualifications and decries him as a fake for exaggerating his condition. She tells Hutz that Dr. Julius Hibbert has been their family physician for years and Dr. Hibbert knows Bart is fine. Later on at the Simpson House, Hutz coaches Bart on exaggerating his condition to help win the jury's sympathy. Knowing what will happen, Marge and Lisa protest against it by telling them about their opinion. They hate the situation as it stands and thinks it is wrong to sue Mr. Burns for that amount of money. Marge and Lisa also insist Bart tells the truth in court. Hutz quickly dismisses their claims, stating what they're doing is the truth.
Both Bart and Mr. Burns present exaggerated memories of the accident on the stand. However, the civil jury is more accepting of Bart's fabricated story and shows sympathy for him. Whereas, Marge and Lisa share a look of disgust and still believe that Hutz made him lie. Things seem to be looking up for Hutz and Homer. After the trial, Mr. Burns is seen yelling at his lawyers when they suggest a settlement because the civil jury hates him. In a last attempt to get them to drop the lawsuit, he invites Homer and Marge to his home. He offers them $500,000 to settle the case and then leaves the room to let them discuss it. Burns listens in on their conversation in the next room by looking through the cut-out eyes of a painting. Feeling guilty that they have been lying, Marge asks Homer to drop the case. He demands to know why she wants him to accept the settlement. Marge reveals she was against suing Mr. Burns from the start and would been very happy with him paying Bart's medical bills and apologizing for the accident. Homer refuses and wants to hold out for the full million by stating that he knows his boss is going to lose the case and will have to pay them anyway. Fearful and upset at his greediness, Marge admits she hates the situation for what it's become, including the use of "phony doctors". Upon hearing that they are using a quack, Mr. Burns walks back into the room, withdraws his offer and releases the hounds.
The next day in court, Mr. Burns' lawyer calls an unprepared Marge to the stand, much to the shock of everyone. She does tell him that she's proud of the fine work that Dr. Hibbert has done because he has real medical qualifications and has been there for the family since she became a mother. When asked about her opinion about Dr. Riviera, Marge is hesitant to tell. Thus, Mr. Burns' lawyer forcibly asks his question again and reminds her that she is under oath. Hutz is concerned because her refusal to lie will destroy the lawsuit and cost them the $1 million. In her testimony, Marge tells the jury the truth by denouncing Dr. Riviera as a fake and outlines how limited Bart's injuries actually were given by Dr. Hibbert. She also reveals that Hutz made him lie about his injuries and being in intense anguish, when he was fine. Marge admits she had a hard time with having Bart at the house for those three days he missed school, even though he hates school. She gives the hardships of the accident a value of five dollars that they would have paid Bart every week to take the trash out, if he had been able to. A stunned Homer listens in disbelief and betrayal as his chances to win the $1 million slips away. As a result, Marge's honest testimony destroys Hutz's case and the family gets nothing. After the case, Mr. Burns offers Homer another check: $0. Realizing they lost the case, Hutz tells Homer they should take it and he does.
That night at dinner, a downbeat and angry Homer blames Marge for costing him the $1 million. Bart is also angry and tells her there was a lot of things they could've done with the money. Homer leaves and goes to Moe's, unsure if he could ever come home again. At the bar, he listens as Moe tries to console him, telling him that rich people aren't happy anyway. Marge follows him there and apologizes for her testimony, even though she did the right thing by telling the truth. However, he is not sure he still loves her after what happened. When Homer looks his wife in the eyes, he says he loves her more than ever.
The episode's plot was based on Billy Wilder's 1966 film, The Fortune Cookie in which Walter Matthau plays a dishonest lawyer who convinces Jack Lemmon's character to fake an injury for a large cash settlement. While working on the court room scenes, director Mark Kirkland watched To Kill a Mockingbird and The Verdict to get ideas for different angles he could use. Although the episode was written by John Swartzwelder, a lot of the ending was pitched by executive producer James L. Brooks. Brooks felt that the episode needed a more emotional ending, so some shots were reworked so that voice-overs could be added.
The episode includes the debuts of three recurring characters, Lionel Hutz, Dr. Nick and the Blue-haired Lawyer. Lionel Hutz was designed by Mark Kirkland, who gave him a evil design, but was asked to make him more "bland looking." He gave him a powder blue suit to make him stand out more. Phil Hartman, who voices Hutz, also guest stars for the first time. He would later become one of the most frequently appearing guest stars, with Hutz and Troy McClure (who was introduced later in the second season) being his most well-known characters.
Dr. Nick Riviera is voiced by Hank Azaria, who used a "bad Ricky Ricardo" impression. The animators modeled Dr. Nick after then-supervising director Gabor Csupo, because they mistakenly believed that Azaria was impersonating him. The Blue-haired Lawyer, who does not have a proper name, was based on Roy Cohn, who became famous as Senator Josepth McCarthy's lawyer. His voice, provided by Dan Castellaneta, was also an impression of Cohn. The devil is also shown for the first time, and he was designed by Mark Kirkland, who originally tried to give him a scary design, but the writers asked him to use a more comedic look.
The show's script supervisor at the time Doris Grau also appears in the show for the first time. She was used because of her unique voice, and appears as a minor character in this episode, but would later become known for voicing Lunchlady Doris.