This article outlines the findings of typological differences between the Level 4 (L4) and Level 5 (L5) of the Interagency Language Roundtable (ILR) in the Russian passages, as explored through the comparative linguistic and content analysis of highly abstract and idiosyncratic philosophical, literary and colloquial perspectives on culture, politics, technology, economics, society, and law. Having reviewed over 100 written and spoken samples from classic and contemporary Russian authors, including literary prose, poetry, dissertations, scientific presentations, debates, satirical pieces, and passages of slang-based correspondence via the internet, we found the ILR-relevant features that would help target language (TL) instructors rate the L4-higher passages for Reading and Listening. (Contains 3 tables and 10 notes.)