The study of Islamic law has naturally focused on aspects of pre-modern legal texts that seem most obviously legal in nature. However, in the post-classical period, new genres emerged that trouble our expectations of what is and is not legal literature. The "non-legal" materials in legal texts are often passed over in silence or dismissed as mere entertainments. Similarly, in the study of literature, the deceptive fatwas, legal puzzles (alghaz), and qadi scenes in the Maqamat of al-Hariri and his emulators have been largely ignored or treated as a curiosity. The shared social and intellectual practices between literature and law in transmitting knowledge can be witnessed on a material level from at least the 6th/12th century. However, it is in the 8th/14th century that these edifying and entertaining narrative materials become fully integrated into recognizably legal texts. This study examines a novel legal genre that reveals the crosspollinations of law, linguistics, and literature. The genre of "Similarities and Resemblances" (al-Ashbah wa-l-Naza'ir) has been described as one dealing with legal maxims (qawa'id), but even as it emerges in the 8th century, it is a complex, synthetic genre. When Taj a-Din al-Subki (d. 771/1370) used the title, he did not discuss solely legal maxims but rather discusses thematically links issues of similarity, difference, and ambiguity. For instance, his text contains stories of scholars who solve legal puzzles (alghaz) in both prose and in verse. The Hanafi Ibn Nujaym al-Misri (d. 970/1563) composed a "Similarities" work made up of seven topics (funun), including legal puzzles, legal devices (hiyal), and anecdotes (hikayat). Although Ibn Nujaym claims that al-Subki is his model, it is al-Suyuti's (d. 911/1505) work in linguistics entitled "Similarities and Resemblances in Syntax" (al-Ashbah wa-l-Naza'ir fi al-Nahw) whose structure of seven topics (funun) likely served as Ibn Nujaym's model. The last topic in both works is anecdotes, a feature not found in al-Subki's work. My paper will focus on the use of puzzles and stories in these three works to demonstrate that the new genres of legal writing reflected complex crosspollinations between linguistics, literature, and law. How were these crosspollinations productive of new ways to organize information? How did authors and readers conceive of the relationship between law, language, and narrative? What was the purpose of including narrative materials in legal texts? What methodologies might scholars use to understand how authors understood the organic links between these seemingly disparate arts?