Middle ear cholesteatoma is a common inflammatory disease that requires surgery due to potentially serious intracranial complications. Diagnosis of cholesteatoma is mainly clinical, with computed tomography (CT) used to evaluate disease extension before surgery. Certain patterns of bone erosion are specific, but CT attenuation does not allow differentiation from other inflammatory middle ear diseases. With its high tissue discrimination and contrast resolution, magnetic resonance imaging is valuable in diagnosis of cholesteatomas. Absent enhancement at delayed postcontrast imaging has been used for diagnosis. Diffusion-weighted imaging (DWI) is highly specific due to the high keratin content of cholesteatomas. New non-echo-planar DWI sequences, such as periodically rotated overlapping parallel lines with enhanced reconstruction, are superior to conventional echo-planar DWI, since they minimize susceptibility artifacts at the skull base and increase sensitivity for detection of lesions as small as 2 mm. This technique is indicated when clinical diagnosis is difficult and high tissue specificity is necessary, as in congenital, temporal bone, or atypical acquired middle ear cholesteatomas and residual or recurrent disease after surgery. Non-echo-planar DWI has been proposed for screening of postsurgical (residual or recurrent) cholesteatomas, thus obviating many second-look revision surgeries, especially after more conservative canal wall up surgery.