Spontaneous pneumomediastinum (SPM) is a rare but potentially life-threatening clinical entity in which free air is introduced into the mediastinum. It most commonly presents in young males and has an incidence of approximately 0.002% of the general population. Symptoms include sudden onset chest pain, dyspnea, neck pain, vomiting, and odynophagia. Physical examination usually reveals subcutaneous emphysema, hoarse voice, tachycardia, tachypnea, and occasionally a Hamman's sign, which is a mediastinal "crunch" sound heard on cardiac auscultation. We present a case of an 18-year-old male baritone player who presented to the ED with chest pain and odynophagia shortly after waking up one morning. The patient's chest radiograph (CXR) revealed free air in the mediastinum with subcutaneous air tracking into the soft tissues of the neck and supraclavicular region. CT of the chest with contrast esophagram confirmed the diagnosis of primary SPM. The cause of his condition was likely due to barotrauma secondary to playing the baritone in his marching band. He had no evidence of esophageal injury or infectious process which further supports the diagnosis of primary SPM. After an extensive workup, the patient was discharged from the ED with instructions on rest, analgesia, and antitussives as needed. Evaluation of chest pain patients in the ED should include a CXR, in addition to other indicated tests, to rule out this potentially debilitating condition. Fortunately, though SPM is potentially life-threatening, most cases resolve spontaneously without surgical intervention.