We have analyzed the preoperative diagnosis of cholesteatoma through the use of diffusion-weighted intensity magnetic resonance (DWI-MR) in 16 consecutive patients suffering from chronic otitis media with clinical and radiological (by computed tomography) suspicion of cholesteatoma. In particular, we compared the radiological data with intraoperative ones, verifying the correspondence (in terms of sensitivity, specificity, positive predictive value, negative predictive value and diagnostic accuracy) between what is reported by DWI-MR and what is actually detectable at the time of surgery. Furthermore, we identified the most reliable DWI-MR sequence [single-shot (SSh) echo planar imaging (EPI) vs. multi-shot turbo spin-echo not-EPI] to detect cholesteatoma and reduce the time for examination. The obtained data on computed tomography scans revealed low diagnostic accuracy (56%); DWI-MR, instead, showed higher values, especially using not-EPI sequences (93.75 vs. 68.75% obtained by SSh-EPI sequences).