This study investigates the physical elements, surface features, readability, rhetorical moves, and politeness strategies employed in job application letters written by Filipino and American teacher-applicants using the lens of contrastive rhetoric analysis. The study analyzed 30 authentic Filipino and American job application letters written from 2001 to 2015, which comprised the entire corpora, using Upton and Connor’s (2001) Coding Scheme and Brown and Levison’s (1987) politeness strategies as frameworks for analysis. The results revealed that the Philippine corpus does not strictly observe the needed physical elements in a job application letter, while the American corpus has consistently adhered to all the required elements. In terms of the surface features of the corpora, Filipino teachers include less words and shorter sentences that are more lexically dense. Meanwhile, American teachers write more words and longer sentences that are less lexically dense. As regards the corpora’s readability, measures of lexical density revealed that American job application letters are more intelligible than those of the Filipinos. However, both of the corpora fall under acceptable ranges of readability based on the Gunning-Fog index. In terms of the rhetorical moves, Filipino teachers follow a more personalized and unconventional way of presenting details in their application letters, while American teachers are more structured and tend to conform to standards in representing each move in their letters. Finally, the preferences of both Filipino and American teachers for politeness strategies show no apparent difference. Filipinos observe direct and nonstandard ways of expressing respect to their addressees. On the other hand, American teachers generally prefer positive politeness strategies and are more indirect, formal, and conventional in expressing congenial statements in their letters. Based on the results, implications for establishing an ESP writing class for teachers are provided.