According to the die cushion apparatus of a press machine and the die cushion controlling method of the present invention, in holding the cushion pad on standby at a desired standby position, it is possible to hold the cushion pad on standby in parallel with the lower faces of the dies mounted to the slide, and if the lower faces of the dies are inclined, it is possible to hold the cushion pad on standby in the state of being inclined. Through this configuration, it is possible to easily allow the material to come into contact with the lower faces of the dies from the beginning of the die cushion force control (beginning of the collision), and also possible to smoothen the die cushion action in the plane, thereby enhancing the formability.