This paper deals with the rough cutting method using 5-axis control machine tool and the tool path generation method to machine complicated shapes efficiently such as overhanging shape that requires the inclination of cutting tool. In general, conventional rough cutting methods employ the contour milling with 3-axis control. However, these rough cutting methods were not always efficient, because several set-up changes were required to machine complicated shapes. The study proposes the new rough cutting method for 5-axis control machining, which uses a plunge milling that has been used only for 3-axis control machining. Consequently, the rough cutting with the high efficiency of plunge milling and the flexibility of 5-axis control can be realized. In order to achieve the method, it is necessary to generate the tool path in consideration of the tool interference with not only the target shape but also the remained part. Therefore, the study developed the tool path generation method by expanding the method which uses the 2-dimensional configuration space technique. Finally, the developed method is implemented to the original CAM software. As a result, it is experimentally found that the system enables the rough cutting of complicated shapes with 5-axis control with only one set-up.