Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2 weeks per grade, to prove that he has what it takes to run the family business.

Sam Giancana is a ruthless mob boss from Chicago. During a trip to Las Vegas, he sees a performance by the McGuire Sisters, a popular singing group with a pure image. Sam is attracted to Phyllis and begins aggressively courting her. The two enter into an epic romance, but it brings unwanted attention and tarnishes Phyllis's reputation. For Sam, however, the consequences are far more drastic, landing him in trouble with the law and his fellow mobsters.

Growing up poor on the streets of New Jersey, Frank Siena (Danny Nucci) has little hope of realizing his dream of becoming a doctor. But "fate" has a way of intervening. Now a brilliant, successful cardiac surgeon, Frank seems to have it all, except for one terrible secret: Before he swore to save lives and do no harm, Frank took another oath... to mob boss Nicola Delarusso (Paul Sorvino), who paid his way through medical school in exchange for absolute loyalty. And when Delarusso demands payment in full Frank suffers a crisis of conscience that could cost him his job, his wife... and his life!

Guy Luthan, a British doctor working at a hospital in New York, starts making unwelcome enquiries when the body of a man who died in his emergency room disappears. After the trail leads Luthan to the door of an eminent surgeon at the hospital, Luthan soon finds himself in extreme danger people who want the hospital's secret to remain undiscovered.

Three lovable party buds try to bail their friend out of jail. But just when the guys have mastered a plan, everything comes dangerously close to going up in smoke.