This article will review the anatomy and common pathologies affecting the peroneus longus muscle and tendon. The anatomy of the peroneus longus is complex and its long course can result in symptomatology referable to the lower leg, ankle, hindfoot, and plantar foot. Proximally, the peroneus longus muscle lies within the lateral compartment of the lower leg with its distal myotendinous junction arising just above the level of the ankle. The distal peroneus longus tendon has a long course and makes two sharp turns at the lateral ankle and hindfoot before inserting at the medial plantar foot. A spectrum of pathology can occur in these regions. At the lower leg, peroneus longus muscle injuries (e.g., denervation) along with retromalleolar tendon instability/subluxation will be discussed. More distally, along the lateral calcaneus and cuboid tunnel, peroneus longus tendinosis and tears, tenosynovitis, and painful os peroneum syndrome (POPS) will be covered. Pathology of the peroneus longus will be illustrated using clinical case examples along its entire length; these will help the radiologist understand and interpret common peroneus longus disorders.