On a Chicago, Illinois, street, an expensive car hits pedestrian Lou Pasquino, and the yuppie driver claims the accident is not his fault. When another pedestrian, Eddie Farrell, suggests that Lou call a lawyer, the driver gives Lou $266 and, at Eddie’s suggestion, his wristwatch. Afterward, Eddie and Lou celebrate their con job. However, local enforcer Pinkie Moreno reminds them they owe gangster Sal Nichols $1,000, takes their $266, and demands the rest by tomorrow. Eddie and Lou try to steal a television by impersonating gas company men, but two young karate students force them to flee. Seeing a suburban house with no lights, Lou and Eddie break in. When the telephone rings, David Malkin announces on his answering machine that he is out of the country, and that Jonathan Albertson is house-sitting in his absence. However, the caller is Jonathan, who apologizes for not being able to house-sit, as he has taken a job in Seattle. Eddie and Lou make themselves at home. Later, Eddie’s mentor, Uncle Max, suggests Eddie rid himself of Lou and move on to bigger things, like stock swindles. Eddie and Lou repay Pinkie at a bar where he plays pool. There, Eddie bets Pinkie $20 he can make a three-bank shot, but when he wins, Pinkie refuses to pay. Ejected from the bar, Lou and Eddie steal Pinkie’s Cadillac, not realizing it actually belongs to Sal Nichols. Calling on the car telephone, Nichols threatens physical harm. In a panic, Eddie and Lou ditch the vehicle in an industrial part of town, where thieves strip the car of its parts. When mobster Nichols finds the remains of his car, $60,000 is missing from the trunk. Although Pinkie names Eddie and Lou as the culprits, Nichols tosses him over a bridge. Eddie and Lou flee as Nichols’s thugs arrive. Eddie takes a taxicab to David Malkin’s empty house. David’s parents, Milt and Mona Malkin, arrive the following morning and mistake him for house-sitter Jonathan Albertson. They invite Eddie to lunch at the country club, and Mona hands him the keys to the house and David’s Porsche in the garage. At the country club, Mona introduces Eddie to her daughter Annie Malkin, who is happy to put a face to the wild person David always talks about. Milt cannot believe “Jonathan” turned down a vice presidency at several corporations, but Eddie explains that he is looking to negotiate oil leases “up north.” Mona is shocked by Eddie’s boorish behavior, but Milt likes him, and takes Eddie to his company, Malcolm Manufacturing, which makes bathroom hand dryers. When a visiting Japanese executive has to use the bathroom, nobody understands him, so Milt Malkin introduces him to “Jonathan,” who spent two years in Japan. Eddie speaks gibberish, and when the Japanese man storms off and gives him the finger, Eddie translates his gesture as “Malcolm [hand] blowers are number-one.” Milt shows Eddie his prized possession: Chicago Cubs star Ernie Banks’s autographed 500th home-run baseball. However, Eddie is more interested in the safe’s $180 thousand in cash. Later, when Eddie explains to Uncle Max that he is unsure what con to play on the Malkins, Max’s wife, Connie, suggests “the love con” on the daughter, but Eddie claims Annie Malkin is too smart and “cold” for him. Connie suggests that Eddie read a few books and “warm her up.” He visits Annie at the clinic where she works as a doctor, and tries to seduce her by volunteering. When she makes him donate blood, Eddie passes out. Later, Mona Malkin invites him to her nephew’s bar mitzvah, and Eddie realizes he is supposed to be Jewish, and watches Fiddler on the Roof for research. At the party, Eddie charms Annie’s favorite grandmother, but Annie is unimpressed. Milt drives Eddie back to David’s house, where Lou awaits, frantic that Sal Nichols has put a “contract” out on them. Eddie covers Lou’s comment for Milt’s sake, explaining that his lawyers will check on the contract in the morning, and introduces Lou as his broker. Milt offers Eddie the vice president in charge of marketing position at Malcolm Manufacturing, and Eddie accepts. During a brainstorming meeting at his new company, Eddie takes Milt and other executives into the men’s room and guides them into the stalls, explaining that people spend over seven minutes a day staring at a bathroom door. He insists that Malcolm is missing an opportunity by not posting advertisements there. Milt declares Eddie a genius. Sometime later, Annie takes Eddie to a nightclub. Pinkie Moreno sits nearby wearing a neck brace. The emcee calls Eddie to the stage, after Annie alerts him of Eddie’s wild side. “Born To Be Wild” begins on the karaoke machine, and the host hands Eddie the lyrics, as the crowd urges him on. Seeing Eddie, Pinkie becomes enraged and rushes the stage, but Eddie kicks him in the head and knocks him out, as he dazzles the audience with his performance. Over the next few days, Eddie and Annie spend time together and fall in love. Milt is impressed with the new bathroom door electronic message boards. When Eddie discovers that executive Paul Chase is taking a valuable client, Donald Williamson, to a Cubs game at Wrigley Field, he sets up a con involving Lou. At the stadium, in a men’s room, Lou dresses as a Secret Service agent, and guides Chase and Williamson into adjoining stalls, then orders everyone to stay put as “Mr. President” is told to come out. With the room empty of witnesses, Eddie iImitates the voice of President George H. W. Bush. Washing and drying his hands with the Malcolm blower, the “President” declares that he must get several Malcolm blowers for his house in Kennebunkport, Maine. Eddie pretends to leave, and Lou, the “Secret Service agent,” hurries Chase and Williamson out of the bathroom and back to the game. That night, Milt toasts Eddie, claiming that Williamson returned to the office begging to make a deal. To show his appreciation, he gives Eddie his Ernie Banks baseball, and Eddie is touched. Later, Annie reveals that “5-9-70,” the date Banks hit his 500th home run, is her father’s license plate number and the combination to his office safe. Realizing how much her father likes Eddie, Annie invites him to spend the night with her. The next day, Eddie tells Lou he loves Annie and wants to call off the con. Lou reveals that a postcard arrived from India stating that David will be returning any day, and suggests Eddie act fast. Eddie races to the clinic, professes his love to Annie, and declares that he has a confession. Believing he wants to marry her, Annie laughs and hurries away before he can say more. When Eddie returns home, Sal Nichols and his thugs are beating Lou. Pointing a gun at Eddie’s head, Nichols demands that the stolen $60,000 be returned tomorrow by four o’clock, and kidnaps Lou as collateral. Later, Eddie robs Milt’s safe and delivers the money to Nichols, and offers the gangster a chance to make more money. Outside, Eddie assures Lou that they will flee to Florida when they finish the con. Eddie suggests that Nichols bribe Gerald Fox, the Chicago Building Commissioner, into granting Nichols’s wrecking company a lucrative demolition job. He takes Nichols to City Hall, where Lou, Uncle Max, and Connie have prepared the “sting” by getting Fox’s secretary out of the office while her boss is at lunch. Pretending to be commissioner Fox, Max offers Nichols a $1.3 million demolition job, which requires Nichols to pay a $250,000 kickback. Nichols agrees, and they set a nine p.m. meet time at the demolition site that evening to exchange the money. Back at David Malkin’s house, the con-artists are surprised to see the Malkins. Eddie introduces Max and Connie as his parents. When David telephones from the airport, Eddie answers the call, and David declares him an imposter. Eddie continues the ruse, welcoming his old friend back before hanging up. Lou, Max, and Eddie hurry to the meet, where Nichols signs the contract and hands over the “kickback” money. Afterward, Eddie returns to the Malkins with the money and confesses that he stole the contents of Milt’s safe. He admits his identity as a con man, and declares that he fell in love with Annie, who slaps him. Eddie leaves as David arrives, and returns the keys to his house and car, complimenting him on his wonderful family. In time, Sal Nichols demolishes the site, which happens to be an Internal Revenue Service building, and he now faces life imprisonment. Milt Malkin replaces the money in his safe and finds that Eddie has returned the baseball. Mona gazes at photographs from the bar mitzvah, and Annie listens to Eddie’s old phone messages. Eddie visits her at the clinic to apologize, and as he leaves, he is struck by a car. Annie rushes to his side and professes her love, as Max and Connie look on from inside the car that ran down Eddie.