We report the imaging findings in two patients with proliferating trichilemmal tumors. In the first patient, the tumor arose on the lower lip, a very unusual location for this type of tumor, and showed malignant transformation with metastasis to a regional lymph node. It was seen as a poorly marginated soft-tissue mass with isointense signal on T1-weighted MR images and hyperintense signal on T2-weighted images. Large areas of high signal intensity caused by necrosis were also found within the tumor on T2-weighted images. After i.v. administration of contrast material, the mass showed significant enhancement, with considerable portions remaining unenhanced. In the second patient, the tumor originated from a preexisting trichilemmal cyst and occurred in the hair-bearing area of the posterior part of the neck. CT scans showed a well-encapsulated cystic mass that contained multiple speckled calcifications in a wall of variable thickness. There were several foci of smooth soft-tissue elevations from the inner wall of the mass, which corresponded histologically to proliferating portions of trichilemmal cyst.