Imitation can be read on a spectrum from sycophantic flattery to cutting mockery depending on the context in which it appears. Inherent in imitation is therefore an evaluative element since the decision to imitate another’s work implies some kind of approbation or condemnation of the source-text. In this regard imitation resembles commentary and may be considered to serve a similar purpose. Khalīl b. Aybak al-Ṣafadī (d. 1363), a prolific writer and commentator on Mamlūk-era literature, was, himself, quite the imitator. His imitations fall along the spectrum of flattery to mockery, but each serves an overall purpose for al-Ṣafadī as he performs his chosen role as curator of cultural authority. This paper will consider three representative examples of al-Ṣafadī’s imitations and reactions to them to consider how we, as readers today, can understand the evaluative or commentarial aspect of his mimicry. The first is Ikhtirāʿ al-Khurāʿ, a short prose text that clearly mocks scholarly literary commentary without dismissing the genre as a whole. The second, a long commentary on a poem known as Lāmiyyat al-ʿAjam by Abū Ismāʿīl al-Ṭughrāʾī (d. c. 1121), is an imitation not only of the stylistics of al-Jāḥiẓ (d. 869), but also in some degree, those of al-Ṣafadī’s contemporary and sometime mentor Ibn Nubātah (d. 1366). Third, are his imitations of Ibn Nubātah’s poetry which drove a wedge between them and in which the line between mockery and flattery blurs. In service to the creation of an authoritative stance, I argue that al-Ṣafadī’s imitations serve three interrelated goals. First, they are showpieces illustrating that he, as author, masters forms he admires be they those of his contemporaries or his predecessors. Second, they are evaluation of or commentary on the source-text depending on whether the imitation reads as mockery, flattery, or something in between. Third, in making evaluations through imitation, al-Ṣafadī describes for himself an authoritative stance within the literary culture. Clever emulation (muʿāraḍah ) takes both literary skill and knowledge and al-Ṣafadī enjoyed showing off his abilities. His imitations often skirt between jest (hazl) and sincerity (jidd) allowing for a display of knowledge and ability within and deriving from the literary tradition. This tendency to play along the edge means, however, that it is not always clear whether the imitations he composed were done in admiration, mockery, or a combination.