in october 1998, it was announced that monica potter had been cast as the lead role of karen sympathy. robert de niro was also announced to be in negotiations for the role of fearless leader, with des mcanuff set to direct from kenneth lonergan's screenplay. in november 1998, jason alexander was cast as boris badenov. in january 1999, rene russo was cast as natasha fatale. in february 1999, potter dropped out from playing karen and was replaced by piper perabo.