After receiving wedding pictures from Rio de Janeiro, Brazil, entertainment attorney Walter Fielding (Tom Hanks) complains to his girl friend, concert musician Anna Crowley (Shelley Long), about his newly married scofflaw father, Walter, Sr. (Douglass Watson). His father might be starting a new life, but he stole the firm's money and ran away to Brazil, and left him and the law firm in debt. The next morning, Walter comments that his father's much younger Filipino new wife, Florinda (Tetchie Agbayani), looks underage. When Anna tells him not to be so conventional, he admits he wants a house in the suburbs, and a wife. When he asks Anna to marry him, she asks for more time to make her decision. Her first marriage to Russian music conductor, Max Beissart (Alexander Godunov), was a disaster, and she is not in a rush to marry again. Suddenly, her former husband's associate, Shatov (Yakov Smirnoff), barges into the bedroom and informs Anna that "Maestro" is returning home, and reclaiming his luxury apartment. Walter and Anna are both broke, and cannot afford to relocate elsewhere in New York City. They decide to contact their friend, real estate broker Jack Schnittman (Josh Mostel), for help. Meanwhile, Max conducts his first rehearsal back in town, and criticizes the orchestra for their mediocre performance. While jogging, Jack Schnittman proposes that Walter gather $200,000 in cash by the end of business Friday because the owners of a $1 million property are willing to sell for less. Walter is suspicious, but feels pressured, and agrees to consider the deal. At dinner, Max tells Anna his life is meaningless without her, and he wants to get back together. Anna insists she loves Walter, and Max only loves himself. Anna goes with Walter to inspect the house Jack recommended. The owner, Estelle (Maureen Stapleton), shows them the property, and explains that Israeli Intelligence arrested her longtime husband, Carlos, for being Hitler's "pool man." If Estelle can sell the property and the furnishings, she might raise enough money to pay the lawyers. Walter and Anna want time to make a decision, but Estelle claims that Carlos is facing extradition, and she must sell immediately. She offers to include an antique Lincoln car in the deal. Walter cannot resist a bargain and convinces Anna to buy the house. She sells valuables from her divorce to raise her share of the money. Walter persuades his client, a successful boy singer named Benny (Billy Lombardo), to loan him the $200,000 in cash to pay for the new house. As soon as Walter and Anna move in, their house falls apart. When the front door is stuck shut, Walter receives an electrical shock as he rings the doorbell. Upstairs, Anna tries out the four-poster bed they acquired with the house, and becomes trapped when the mattress collapses around her. When Walter knocks to get Anna's attention, the front door falls down. He turns his attention to repairing the staircase, but his hammering loosens the ceiling plaster upstairs. In the bathroom, Anna is revolted when she turns on the bathtub faucet, and gooey, rusty water spurts out. Walter assures her that all houses need maintenance, and encourages her to be more positive. As Anna hangs her clothes in the bedroom closet, the rod and shelving collapse. Outside, Walter repairs the front door. He tests it three times and goes inside, but within seconds, the door frame separates from the structure, falling to the ground. Upstairs, when Anna pulls the dumbwaiter ropes, a raccoon emerges and attacks. Walter hears Anna's screams, but as he races up the staircase, it collapses around him. Walter is convinced the house is "a lemon," and that Estelle swindled them into buying that faulty house, but Anna will not let him quit. However, a rainstorm reveals that there are several leaks in the roof. The next morning, a carpenter named Art Shirk (Joe Mantegna) arrives to do an estimate on a new staircase, and declares that the front door has dry rot. Art's plumber brother, Brad (Carmine Caridi), arrives, and insists on a $5,000 upfront check without even inspecting the house. He claims to have seen the house several years earlier, and does not expect the plumbing problems have been resolved. Later, electrical fires occur when too many appliances are used. The blender and the popcorn popper explode, and the stove doors burst open. The turkey is propelled out one window and bursts through a second floor bathroom window. As Anna and Walter pour buckets of lukewarm water in the bathtub, the rotting floor gives way, and it crashes onto the floor below. The next day, Brad Shirk's foreman, Curly (Philip Bosco), arrives with a crew that looks like a gang of Hell's Angels. Curly encourages Walter and Anna to leave while they work on the house. Walter returns to find piles of debris everywhere after the group had trashed the house even more. Since Walter was not available to sign building permits, Curly and his crew went as far as they could. He promises to return when Walter has his permits approved. The "permit man," Mr. Shrapp, agrees to return if Walter pays a cash bribe. Soon, Walter falls into a hole in the floor concealed by a throw rug. Mr. Shrapp arrives, and believes he hears Walter laughing instead of answering the door. Angered by Walter's rudeness, Mr. Shrapp rips up the permits and leaves. Anna calls Walter to be picked up at the train station, but he cannot answer the phone. She hitches a ride with a truck driver, and finds Walter stuck in the floor. When she attempts to rescue him, he plummets to the floor below. That evening, when Walter puts another log in the fireplace, the chimney comes crashing down, and snuffs out the fire. Four months later, the house is still under repair as a more competent work crew fixes all the damages and patches up the holes in the floor, walls, and ceiling. Walter complains that Curly estimated the job would be done in two weeks. However, things are looking up. A new staircase and running water in the kitchen are the latest improvements, but accidents continue to occur. At an orchestra rehearsal, Max persuades Anna to have dinner at his apartment. Although she claims she will not sleep with him, they drink too much, and in the morning, Max tells her they made love, and she is consumed with guilt. Later, Anna tells Walter that Max took orchestra members to dinner after a brilliant rehearsal. When Walter wants to know if she spent the night with Max, Anna insists he will have to trust her. They argue as Anna lies about her indiscretion. When she finally confesses, Walter spends the night downstairs. In the morning, the fight continues. Walter want to kick her out of the house and refund her money. The workers listen in as she claims the house belongs to her just as much as it belongs to him. Finally, they agree to stay together until the repairs are done, sell the house, divide the money, and split. Anna retreats to the bedroom and sobs. Later, Max makes a surprise visit, and learns that Anna and Walter have decided to break up. He suggests that Anna should rekindle their relationship, but that is not part of her plan. Max confesses they did not sleep together, but lied to sabotage her relationship with Walter. When he sees how much she actually cares for Walter, Max decides to play matchmaker. He warns that it would be a mistake for Walter to throw away his relationship with Anna. Another few days later, when the house is finally renovated and restored, Walter and Anna are confused about where to take their relationship. Walter confesses he will get over Anna's one-night stand with Max. Anna tears up as she reveals she never slept with Max. They fall into each other's arms and kiss. Anna and Walter throw a wedding in their new home and Max conducts a full orchestra as part of the entertainment. Despite the repairs to restore their new house cost more than the $200,000 in cash that they used to purchase it, Walter and Anna are finally happy and that their "money pit" of a house is finally livable and everything is great. In Rio de Janeiro, the crafty con artist Estelle and her partner-in-crime Carlos (John van Dreelen) resurface where they offer to sell a house to Walter, Sr. insisting it must be a cash deal... and the vicious cycle is about to start all over again.
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