Tears can be cathartic. They help us process extreme happiness or sadness. But a tearless response can be equally profound. Take Winterreise, the 1827 song cycle about a lovelorn wanderer’s desolate winter journey. It ranks as one of the bleakest, most moving statements of German Romanticism, thanks to the alchemy between Franz Schubert’s music and Wilhelm Müller’s poetry. Yet in almost 30 years of performing it, tenor Ian Bostridge has only seen one spectator cry. Something about the piece prompts us to internalise our emotions.

So Bostridge argues in Schubert’s Winter Journey: Anatomy of an Obsession, his new book about Winterreise. In the process he delivers a mini-lecture, explaining that the cult of sensibility and its encouragement of expressiveness — a product of the mid to late 18th century — had, by the 1820s, become the subject of mockery.

Such lateral thinking exemplifies Bostridge’s aim: to illuminate the enigmatic “Mount Everest” of song cycles with any fact or finding at his disposal. And he has gathered quite a few. History, literature, visual art, etymology and years of musical experience are brought to bear on his analysis of these 24 songs, each addressed in a separate chapter. What emerges with compelling force is the author’s intellectual curiosity and passion for his subject. He has, after all, been obsessed with German song — the Lied — since first encountering it as a schoolboy, and has performed Winterreise around 100 times.

As he points out, he does not have a musicological background, and this book is far from a technical guide to the work. Not that Bostridge lacks academic credentials: he has an Oxford doctorate on witchcraft in 17th- and 18th-century England, and in 2011 published A Singer’s Notebook, a collection of essays. In Schubert’s Winter Journey every chapter is crammed with original insights, generating a complex discussion.

Schubert’s protagonist is central to this. Is he an everyman, a Byronic figure deliberately shrouded in mystery? He might be an existentialist in a meaningless, indifferent world, someone akin to a character in a Samuel Beckett play. Perhaps he is a stranger in his own country, not unlike Schubert and Müller themselves. On this point Bostridge is particularly forthcoming, tirelessly decoding references in songs including “Gefrorne Tränen” to a post-Napoleonic Vienna “frozen” by Prince Metternich’s repressive regime.

Or perhaps the wanderer’s sense of alienation stems from another source. In 1815 a new Austrian law was passed preventing men of insufficient means from marrying. That may be why Schubert was unable to marry his neighbour Therese Grob, as he had hoped. Another love, for a woman of a much higher social status, similarly came to nothing. It’s not surprising, Bostridge concludes, that he eventually contracted syphilis, most likely in a “run-of-the-mill bordello”. And the impact of that fatal disease is vividly spelt out in the book, along with its array of humiliating treatments: “A hot room (up to 29 degrees centigrade) with no open windows. No change of underwear or bedding, no washing except rinsing the mouth . . . An unguent of lard and mercury was to be applied to various parts of the body every second day.” It’s easy to see why Winterreise, on which the composer worked in his last months, is full of “cutting sarcasm”, “profound misanthropy” and whispers of death.

Above all, it is marked by a duality between “the expression of true emotion, and a sort of ironic distancing from it, even an embarrassment at it”. Bostridge reads repressed grief into “Gefrorne Tränen”, repressed sexuality into “Erstarrung”, satirised sentimentality into “Frühlingstraum”. More intriguingly still, he explores the song cycle’s similarly troubled performance history, questioning, in particular, what it was that the Nazis liked so much about Winterreise. Was it the Romantic fascination with death?

Where Bostridge particularly triumphs is in the bold connections he makes: between the crow in “Die Krähe” and artwork by Caspar David Friedrich; the humble charcoal burner of “Rast” and the Carbonari — the revolutionary secret society of 1820s Italy. What this book lacks, however, is a clear train of thought. Like Winterreise’s anti-hero, Bostridge is inclined to meander. There is much repetition and fact-flaunting — do we really need eight pages on the Earth’s geological evolution, informative as they are? As a result, Schubert and his wanderer tend to get lost in digression. Nevertheless, Schubert’s Winter Journey provides a fascinating insight not just into the song cycle and the mindset of its composer but also that of a leading interpreter.

Schubert’s Winter Journey: Anatomy of an Obsession, by Ian Bostridge, Faber £20, 544 pages

Hannah Nepil is an FT music critic

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