Radiologic findings of six cases of malignancy associated with chronic empyema 5-39 years in duration were reviewed. Pathologic examination confirmed three B-cell non-Hodgkin lymphomas, one round-cell sarcoma, one mesothelioma, and one adenocarcinoma. Retrospective findings on plain chest radiographs suggested the occurrence of malignancy: increased radiopacity in the thoracic cavity, soft-tissue bulgings and/or unsharpness of fat planes in the chest walls, destruction of bone near the empyema, and extensive medial deviation of the calcified pleurae. Computed tomography delineated masses with soft-tissue attenuation more clearly than radiography in all cases. Magnetic resonance images of three cases were informative because empyema cavities were surrounded by low-intensity rims, and two of them showed a signal intensity different from that of necrotic tumors. Scintigraphy revealed increased uptake of gallium in all cases. Ultrasonography was useful for biopsy guidance. Every radiologist should know this entity in observation of chest radiographs obtained in patients with chronic empyema, and further radiologic assessment and aggressive biopsy are recommended if malignancy is suspected.