Matthew records six instances in which Jesus expressed the idiom ‘weeping and gnashing of teeth’ (8:12; 13:42; 13:50; 22:13; 24:45; 25:30). The phrase refers to the eschatological fate of the wicked. This article investigates whether those who weep and gnash their teeth suffer physically, or merely spiritually and emotionally. A word study of the ‘weeping’ and ‘gnashing’ revealed that both these terms contain within their connotation the aspect of weeping and gnashing of teeth that is a direct result of physical pain. The use of the ‘furnace of fire’ and ‘cut him in pieces’ similarly seems to associate the idiom with suffering as a direct result of physical pain.