Rudy Baylor (Damon) is a graduate of the University of Memphis Law School. Unlike most of his fellow grads, he has no high-paying job lined up and is forced to apply for part-time positions while serving drinks at a Memphis bar.Desperate for a job, he reluctantly is introduced to J. Lyman "Bruiser" Stone (Mickey Rourke), a ruthless but successful ambulance-chasing lawyer, who makes him an associate. To earn his fee, Rudy is required to hunt for potential clients at a local hospital. He meets Deck Shifflet (DeVito), a less-than-ethical former insurance assessor, now a paralegal who has failed the bar exam six times. However, Deck is resourceful in gathering information and practically an expert on insurance lawsuits.Rudy has just one case, one of insurance bad faith. It could be worth several million dollars in damages, but his personal life is falling to pieces and he is about to declare himself bankrupt. When his employer is raided by the police and the FBI, he and Deck set up a practice themselves. They file suit on behalf of a middle-aged couple, Dot and Buddy Black, whose 22-year-old son Donny Ray is dying of leukemia, but could have been saved with a bone marrow transplant, denied by their insurance carrier Great Benefit.Rudy passes the Tennessee bar exam but has never argued a case before a judge and jury. Now he finds himself up against a group of experienced and devious lawyers from a large firm, headed by Leo F. Drummond (Voight), a showman attorney who uses unscrupulous tactics to win his cases.The original judge assigned the case, Harvey Hale, is set to dismiss it because he sees it as one of many so-called "lottery" cases that slow down the judicial process. But a far more sympathetic judge, Tyrone Kipler (Glover), takes over when Hale suffers a fatal heart attack in his swimming pool. Kipler, a former civil rights attorney, immediately denies the insurance company's petition for dismissal.While preparing his case, Rudy seeks new clients and meets pretty Kelly Riker (Danes), a battered wife whose husband Cliff's savage beatings have put her in the hospital. He persuades Kelly to file for divorce, but this leads to a confrontation with Rudy that results in the abusive husband's death. To keep Rudy from being implicated, Kelly tells the police she was alone and killed her husband in self-defense. The district attorney declines to prosecute her.Donny Ray dies, but not before giving a video deposition in the front yard of his home. The case goes to trial, where Drummond preys on Rudy's inexperience. He gets the vital testimony of Rudy's key witness, Jackie Lemanczyk, stricken from the record. Nevertheless, thanks to Rudy's single-minded determination and skillful cross-examination of Great Benefit's unctuous president, Wilfred Keeley, the jury finds for the plaintiff.It is a great triumph for Rudy and Deck, at least until the insurance company quickly declares itself bankrupt, thus allowing it to avoid paying fifty million dollars in punitive damages. There is no payout for the grieving parents and no fee for Rudy.Deciding that this triumph will create unrealistic expectations for future clients, Rudy decides to abandon his new practice after only one case to teach law with a focus on ethical behaviour instead. Furthermore, he leaves town with Kelly, out of a desire to remain low profile and protect Kelly from any possible retribution from Cliff's vengeful relatives.
Output: Question: How many times did Deck Shifflet fail the bar exam ?, Answer: Six