A material handling device includes a vacuum cup pivotally attached to a receiving collar and pivotable to engage a surface of an object to be picked up by the material handling system. The receiving collar includes a support post and a mounting collar that is movable along the support post. The mounting collar is attachable to a support assembly that is movable to move the device toward and into engagement with the object. The mounting collar may move along the post after the respective cup engages the object and while the cups of other devices of the system are moved further toward and into engagement with the object. The material handling device may include an object sensor at a generally central region of the vacuum cup. The material handling device thus is configured to engage objects having uneven surfaces and having varying surface levels from one object to the next.