A plungeable cutting apparatus can include a cutting tool having at least one cutting insert. Each cutting insert can have a body sized and configured to define at least one cutting edge that is positioned for cutting into a work piece to define a recess, groove or other type of aperture. Some embodiments of the cutting apparatus can utilize an array of cutting inserts positioned along a distal periphery of a cutting tool of the cutting apparatus, for example. Each cutting insert can have a generally square configuration or other suitable shape. Some embodiments can be sized and shaped to help limit vibration during metalworking to help improve the life of the cutting insert and facilitate larger sized aperture formation via plungeable cutting operations that may also need less finishing work.