A high jugular bulb is often discovered as an incidental finding that is asymptomatic. Conductive hearing loss in association with this anomaly may occur, but has been reported infrequently in the literature. We report five cases of high jugular bulb and associated conductive hearing loss. Mechanisms to explain the conductive hearing loss include contact of the jugular bulb with the tympanic membrane, interference with the ossicular chain, and obstruction of the round window niche. The operative findings, radiographic and audiometric data that support these mechanisms of conductive hearing loss are presented.