Dermatomyositis is an uncommon inflammatory condition characterized by proximal muscle weakness with distinct cutaneous manifestations. Like any other systemic disease, it affects multiple organs, the lungs being one of them. Common pulmonary manifestations of dermatomyositis (DM) include interstitial lung disease (ILD), primary lung malignancy, and aspiration pneumonia. The involvement of the pleura is not commonly seen, and pleural effusion is rarely reported in DM. Its presence should prompt further workup, especially for malignancy. An association between dermatomyositis and malignancy has been studied widely and is well established. Here, we report a 37-year-old female with classical cutaneous manifestations and myopathy of dermatomyositis presenting with a malignant left-sided pleural effusion.