Nick Hendricks ( Bateman ) and Dale Arbus ( Day ) are friends who despise their bosses . Nick works at a financial firm for the sadistic David Harken ( Spacey ) , who implies the possibility of a promotion for Nick for months , only to award it to himself . Dale is a dental assistant being sexually harassed by his boss , Dr. Julia Harris ( Aniston ) ; she threatens to tell his fiancee Stacy ( Lindsay Sloane ) that he had sex with her unless he actually has sex with her . Nick and Dale 's accountant friend Kurt Buckman ( Sudeikis ) enjoys working for Jack Pellitt ( Donald Sutherland ) at a chemical company , but after Jack unexpectedly dies of a heart attack , the company is taken over by Jack 's cocaine @-@ addicted son Bobby ( Farrell ) , whose apathy and incompetence threaten the future of the company .