Mimesis is a Greek word that means to imitate, while the word masquerade means pretending to be something or someone that he/she is not. In this case series of four cases pertaining to different organ subsets, we discuss and highlight the benign medical conditions, which pretended as neoplastic both clinically and radiologically preoperatively; however, the postoperatively histopathological report yielded surprising results. Though lots of literature on a malignant masquerade is available, there is a paucity of data on case series discussing the different subset organ involvement. These unique clinical scenarios also emphasize the fact that it is incorrect to judge a book by its cover. We would like to summarize our humbling experience in the word of William Osler “medicine is the science of uncertainty and art of probability.”