A modular cutting tool assembly inludes a tool holder having at least one insert receiving pocket, and at least two cutting inserts interchangeably receivable within the pocket. The pocket has a first lateral support surface forming an angle .theta. with a second lateral support surface as measured in a plane perpendicular to the pocket axis. Each of the cutting inserts has a peripheral flank surface configured to provide a number of abutment features appropriately angled for positioning in abutment with the lateral support surfaces. The peripheral flank surface of one cutting insert is further configured to provide at least two cutting points having a first nose angle, and the peripheral flank surface of the other cutting insert is further configured to provide at least two cutting points having a second nose angle different from the first nose angle.