In the course of a 1998 interview, legendary free improvisation guitarist Derek Bailey was played 14 tracks and asked to identify them. Despite the fact that no one could question his encyclopedic knowledge – hearing Bailey discuss music, in general, was like hearing Keith Richards discourse on blues, minus the bourbon – his response was “they all sound the bloody same to me”.

How could someone so musically literate sound so bewildered? One thing uniting many of the players and composers at the outer reaches of music and sound art is what is at best an ambivalence towards, and at worst a detestation of, recording, and that was the problem for Bailey, a man passionately committed to the live experience. All 14 of the tracks he was played were recordings, and despite their different players, genres and styles, this was enough to make them seem interchangeable.

This ambivalence is a central theme of David Grubbs’ Records Ruin the Landscape. Specifically, his interest is in experimental music of the 1960s, “music that was heard by the smallest of coteries in the early 1960s but is now available to what would have been an unimaginable audience of potential listeners”.

A central figure here is John Cage, and Cage’s opposition to records is legendary. In public lectures, he often illustrated the musically stultifying effect of fixing a performance on disc by recalling a concert featuring Stravinsky’s Firebird, conducted by the composer. A boy in the audience, obviously familiar with the suite on record, turned to his mother and said authoritatively, “That’s not how it goes.”

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Grubbs points out a further paradox. Those, like Cage, who have huge misgivings about records often wind up making them, not least because recordings are vital to the growth of enthusiasm for, and awareness of, even the most transitory of sound art. Grubbs treats three of the earliest releases of Cage’s music – the 25-Year Retrospective, Indeterminacy and the Time recording of Cartridge Music – both in terms of the role they played “in forging his public identity” and of the impact they had on an up-and-coming generation of artists in the 1960s.

He also examines “the dramatic change in access to archival recording that has taken place through online dissemination”. He provides “analyses” (as he puts it) of two influential websites, DRAM and UbuWeb.

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As is so often the case when people start to gush about streaming, the discussion risks being politically and sociologically naive. According to its founder, UbuWeb’s manifesto is “UbuWeb wants to be free”, playing on Stewart Brand’s assertion, so dear to hackers everywhere, that “information wants to be free”. However, to paraphrase Morton Feldman in turn, most streaming sites are not free – they’re fighting over pieces of advertising revenue. (Fortunately, a brief parsing of the scripts running on its site reveals UbuWeb as a refreshing exception.)

This is an engaging book, but does it ever go anywhere? Among the historical insights and the insightful observations – and there are many – it’s hard to escape the feeling that here are five chapters in search of a thesis. After talking about Cage, for instance, Grubbs is suddenly writing about Luc Ferrari’s tape piece Presque rien. The discussion is interesting, but – like the free associations of an elderly aunt that lead her unexpectedly to talk about next door’s whippet – how did we get there? When we read Jacques Derrida (if we read Derrida), the lack of a unified direction is never a problem (even if you miss the resolution of knowing whether the butler did it), but the absence of such old-fashioned clarity is unconstructively unsettling when it reads like Dan Brown.