The ultimate success or failure of a restored tooth is dependent on clinical management such as material choice, cavity design, bonding techniques and others. The current paper adopts a fundamental result in the linear theory of elasticity on the singular stress distribution in bi-materials wedge to analyze the choice of different materials used for the restoration of a tooth. Based on the value of the strongest singularity, different restorative materials are evaluated in terms of the susceptibility to the tooth fracture. Comparable results are reported for amalgam, gold alloys, and ceramic materials. Due to a wide variety of mechanical properties the application of resin composites could lead to better or worse fracture resistance of the restored tooth. The theoretical findings are supported by current clinical reports on longevity of restored teeth.