Disclosed are a variety of arcuate-shaped inserts for drill bits, and in particular, for placement in rolling cone cutters of drill bits. The arcuate inserts include 360° or ring-shaped inserts, as well as inserts of smaller arcuate length. The arcuate inserts are suitable for use in all surfaces of the rolling cone cutter, and in other locations in drill bits, and may have specialized cutting surfaces and material enhancements to enhance their cutting duty performance. Certain arcuate inserts may include stress relieving discontinuities such that, upon assembly into the cone or during drilling, the arcuate inserts may fragment in a controlled and predicted manner into shorter arcuate lengths.