Difficulty is most often associated, not with popular music, but with the avant-garde. How do popular music listeners listen to albums that present compositional, performance or conceptual elements from the avant-garde? This paper explores where difficulty lies for listeners when they listen to, situate and evaluate albums that sit on the intersection between the popular and the avant-garde. The paper focuses on the online collaborative discourse of readers of a British music magazine (The Word), to explore how, while ‘difficult albums’ might be considered sui generis and dislocated from the norms of popular music, the aesthetic discourse of The Word's readers shows that to engage with difficult albums is to explore how they are able to be connected with a range of musical histories and practices, as well as to multiple personal experiences of popular music.