Sometimes it doesn't matter a damn. Recordings of Fats Waller will make me dance and smile, despite the limited dynamic range and technical clarity of the original 1930s recordings. However, the arrangement of the music and the role of the band (piano, gypsy guitar, trumpet, vocals) are more than clear enough to impart the emotion of the music.
Big speakers. We don't just listen with our ears. We can feel music through our bodies at louder volumes. In addition, we can sense frequencies below 20Khz through our skeletons. Witness deaf percussion players, and the presence of church organ pipes at sub 20Khz frequencies (Stephen J Gould notes this in his essay 'An earful of jaw' since our inner-ear bones evolved from our jaw bones). Generally, I find that with larger speakers, it is possible to hear the music clearly, and at the same time have a conversation without straining.