Pleural metastatic melanoma is rare, and associated malignant pleural effusions are even rarer. We present a case of pleural metastatic melanoma with recurrent malignant pleural effusions. The initial diagnosis showed no metastatic disease, and the patient underwent resection and received a year of immunotherapy for localized disease. However, two years later, the patient presented with pleural metastatic melanoma with unresolving malignant pleural effusions requiring an indwelling pleural catheter and eventually, thoracotomy with decortication. Clinicians should have a high index of suspicion for pleural metastatic melanoma in the setting of recurrent pleural effusions, even though it is a rare occurrence.