Directed by John Byrum, The Whoopee Boys follows two down on their luck dim witted New York street peddlers called Jake Bateman (Michael O’Keefe) and Barney Bonar (Paul Rodriguez) who hustle a Cadillac and drive to Palm Beach. Upon arrival they accidentally gate crash an upper class party held by a rich elderly couple who lost their dog, Ralph.
At the party Barney’s tries but fails to befriending a Navy admiral and his wife whilst Jake meets Olivia (Lucinda Jenney), 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.
As the film develops Olivia and Jake begin to get a little close but just before anything happens she drops a bombshell on Jake. It turns out Olivia is to be married to someone her uncle approves and her uncle will only accept a man to marry her if he is a “perfect gentlemen”. On top of that, if she cannot marry in 30 days, she will lose her orphanage to a real estate developer, Strobe (Stephen Davies), who just also happens to be Olivia’s jealous ex-boyfriend! Keith David pops up too!
Jake offers to marry Olivia, but she is convinced that Jake is not going to be good enough for her uncle. Will he convince the Uncle, save the orphanage, and marry Olivia?