After tafseer had become a scientific discipline dedicated to the Qur’an, works that were explicating manuscripts except the Qur’an and written for this purpose were named commentaries. In other words, a commentary is an explanation provided by someone who claims that he/she understands the text better than the other readership. The commentaries have undertaken the role of translating, explaining, and interpreting the diverse scholarly works written in many branches of science—from mathematics to astronomy and from rhetoric to logic—and have an exceptional place in Turkish history of literature. The literary commentaries, written for the Arabic and Persian classics have become a unique field within our literature. These works, which have a wide range of objectives, ranging from the reinterpretation of classical Islamic civilizations to the teaching of languages, contain seriously philological, literary, historical, etymological, lexical, mythological, cultural materials and knowledge. Sa’dî-i Şîrâzî’s work, Bostân, which he completed in 1257, is one of the commented classics of Islamic civilization. Bostân written in the form of mathnawi poetry style has become a work that has been widely read from the day it was written until today and it has been accepted as one of the main sources of learning for those who want to learn Persian. The work is inspired by the events that Sa’dî-i Şîrâzî has seen, heard or personally experienced and composed of stories written by him about politics, good morality, love, consciousness of being a servant, beneficence, thrift, consent and decency. This work, which is also loved by Turks, has many translations and commentaries. Sûdî-i Bosnevî and Şem’î, are contemporary and eminent commentators who wrote significant works in Turkish commentary literature and they both commented on Bostân. These two commentaries, which were made on the same source text and in the same century by different commentators, shed light on the tradition of commentary literature with their intersecting and diverging points in the sixteenth century, in which literary commentaries emerged. The presence of myriad copies of the manuscripts of two Bostân commentaries in different periods is an indication that they are among the works that were read intensely during and after the mentioned period. Both Sûdî-i Bosnevî and Şem’î commented on works apart from Bostân. As far as the clues reveal in their works, the two commentators had met and discussed as much that they would have opinion about each other, and both had read and studied each other’s works. It is understood from the refutations in their works that they had bitterness between them as a result of practicing in the same field, rivalry or other personal matters. In these refutations, they went beyond revealing the literary mistakes of each other and expressed negative opinions about each other’s characters. It is possible to say that Sûdî-i Bosnevî is more sharp-tongued and rough-styled in this manner. The attitude of Sûdî-i Bosnevî against Şem’î in his refutations is so harsh and cruel that it can overshadow the literariness of his work. In fact, in some of his utterances and expressions insults can be noticed about Şem’î. However, the work of Sûdî-i Bosnevî is more systematic and elaborate than the work of Şem’î in terms of technique and content. While the couplet was commented upon, it had been studied meticulously and carefully in every stage from the explication of grammatical elements to word denotations, from literary arts to translations. Both the copy differences and mistakes of Sürûrî and Şem’î, who commented earlier on Bostân, are taken into consideration, and the substantial effort has been made for translation to be the closest to the original. In the work of Şem’î, there is a translation in the center of the commentary. The commentator interprets each couplet by separating them verse by verse, and used annotations to explain the elements that he thinks are difficult to be understood. However, these explanations are very limited compared to those of Sûdî-i Bosnevî, and they are also superficial and weakly informative. It can be noted that Şem’î is qualitatively inferior to that of Sûdî-i Bosnevî in terms of the translation of the couplets. The translation of the Sûdî-i Bosnevî, which is far superior to that of Şem’î in attributing meaning to words, recognizing the Persian metaphor and translating it into Turkish, is much more robust and successful than Şem’î’s translation. However, it can be seen from time to time that Şem’î’s commentary of Bostân gives Arabic meanings of the words, used in couplets, alongside their Turkish meanings, as does Sûdî-i Bosnevî’s commentary of Bostân. Şem’î noted copy differences and for better understanding of the verses, he transformed them into plain sentences under the name of “takdîr-i kelâm” and wrote a refutation concerning the reviews of Sürûrî, who had written commentary for Bostân earlier which he considers mistaken. In this context, the comparative study of Sûdî-i Bosnevî’s commentary of Bostân and Şem’î’s commentary of Bostân, within the tradition of Turkish commentary literature, constitutes the subject of this work.