Two dim-witted New York street peddlers, Jake Bateman and Barney Bonar, have grown tired of the frozen cold. They head to a car place where drivers are hired to transport vehicles. When they are denied driving a Cadillac to Palm Beach, Florida, Jake flirts with the car place owner and threatens to eat her goldfish until she agrees.
Upon arriving in Palm Beach, the duo find themselves accidentally crashing a party held by a rich elderly couple who lost their dog, Ralph. Barney's attempt at befriending a Navy admiral and his wife doesn't go too well while Jake meets Olivia, an heiress who runs a local orphanage. When Jake and Barney leave to find the Cadillac had been towed, Olivia offers to take them in in exchange for help at the orphanage. Olivia and Jake begin to get a little close when she drops a bomb on Jake. She is to be married to someone her uncle approves. Her uncle will only accept those whom he considers "perfect gentlemen". If she cannot marry in 30 days, she will lose her orphanage to a real estate developer, Strobe, who just also happens to be Olivia's ex-boyfriend who can't seem to let her go. When Jake offers to marry Olivia, she is convinced that Jake is not going to be good enough for her uncle.
Upset, Jake turns to Barney, who suggests they go to a charm school run by Henrietta Phelps, a well known expert in etiquette. Taking the back route to the school, Jake and Barney are joined by the nerdy Eddie Lipschitz, aggressive police officer White, neurotic Shelley, Indian man Roy Rajmataj, and Claudia, the pregnant wife of a Mafia boss. At first, things don't bode well for anyone in the group. One night, Jake and Barney sneak off to a local bar where they find Henrietta's husband Colonel Phelps. The Colonel reveals he is part of a secret society similar to the Illuminati in terms of learning how to be a perfect gentleman. The duo splits their time between the couple, learning proper etiquette from Henrietta while the Colonel has the boys take mock photos with royal figures and government politicians to make themselves established.
Having finished both courses, Jake intends to win back Olivia. However, he must deal with the likes of Strobe and his two right hand men, Whitey and Tipper. To impress Olivia's uncle, Judge Sternhill, Barney brings in some of his friends from the charm school to help Jake. For instance, Officer White gives Barney a machine gun to help Jake shoot skeet successfully with Barney actually pulling the trigger. When at a party, Jake manages to make Strobe look foolish, the Judge is disappointed with both men and suggests a game called "cross courts", the two get Eddie to join in. However, when Eddie unwittingly confesses to Whitey about charm school, the ruse is up and Olivia is forced to marry Strobe.
At the wedding ceremony, Jake and Barney sneak in while Claudia comes in as a guest. Officer White distracts the priest and "arrests" him. Roy disguises himself as the priest with Eddie posing as an altar boy. When Strobe unveils the bride, it is actually Barney in a wig and totally embarrassing Strobe. Jake and Olivia finally get Sternhill's approval and Strobe is arrested by Officer White. Jake and Olivia drive off while Barney meets two women coming out of the church. The finale sees Judge Sternhill finding Colonel Phelps and they both give off the secret sign that they were both members of the "secret society" that Jake and Barney had become the newest members of.
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