Despite condylar fractures representing one of the most common sites of mandibular fractures, intracranial condylar dislocation is a rare event. In this article, the authors report 2 patients. The first patient is a young female with signs and symptoms as commonly reported in the literature. The second patient reports the consequences of a delayed diagnosis of intracranial condylar fracture dislocation. Both patients underwent surgical treatment. These patients are discussed with a review of the literature, noting biomechanics and mechanism of injury, diagnostic methods, and the treatment for these fractures. Diagnosis also may be challenging at times, though it should always be suspected in patients with bite alterations associated with high energy trauma and the stigmata of direct chin trauma. There is no pathognomonic clinical examination and it is fundamental to use computed tomographic methods for confirmation. Treatment is often open reduction and internal fixation, though it should be tailored for each patient presentation.