Overboard derives much of its humor from having its characters anachronistically placed in modern times. For instance, they put quarters in dockside parking meters, order pizza by cellphone, and have a company health insurance plan. Competence is also an issue. While the Overboard crew carries cutlasses and makes raids, most often their treasure is stolen by disgruntled shipmates or by more able pirates. The captain has made a horrendous mess of the investments for their pension fund (at one point, he adjusts his failed investment strategy by flushing cash straight down the toilet).