There are many kinds of extra-axial brain tumors and tumor-like lesions, and definitive diagnosis is complicated in some cases. In this pictorial essay, we present rare and challenging extra-axial brain lesions including neuroenteric cyst, primary leptomeningeal melanomatosis, isolated dural neurosarcoidosis, intradiploic epidermoid cyst, ruptured dermoid cyst, intraventricular cavernoma, and cavernous hemangioma of the skull with imaging findings and clinico-radiological differential diagnosis, including the pathologic correlation. Familiarity with these entities may improve diagnostic accuracy and patient management.