“Al-Jāhiliyya” evokes vivid images of idol worship, tribalist antagonisms, and violence commonly assumed to be emblematic of the Muslim representation of pre-Islamic Arabia as a “barbaric” anarchical society. Such associations, however, overlook manifold complexities of the era’s portrayal in classical Arabic literature, and this paper calls for a more nuanced reading of classical narratives of al-Jāhiliyya. Exploration of the word’s semantic shifts evidenced in Arabic lexicography and Qurʾānic exegesis between the third/ninth and seventh/ thirteenth centuries reveals that only after the fourth/tenth century did the now common Jāhiliyya stereotypes become virtually synonymous with pre-Islam. Via a survey of third/ninth century Arabic writings, this paper also explores how and why certain discourses articulated rather positive memories of pre-Islamic times.