A front and back chamfering rotary milling cutter includes a cutter body including an insert pocket and a star-shaped indexable cutting insert releasably retained in the pocket. The cutting insert has star-shaped upper and lower surfaces connected by a peripheral surface intersecting each of the upper and lower surfaces. The cutting insert includes a plurality of circumferentially alternating inner and outer corner portions. A cutting portion is defined by each outer corner portion together with an adjacent first inner corner portion rotationally forward thereof and an adjacent second inner corner portion located rotationally rearward thereof. Each cutting portion includes a front chamfering cutting edge extending from the outer corner portion to the first inner corner portion and a back chamfering cutting edge extending from the outer corner portion to the second inner corner portion.