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Eminent Hipsters, by Donald Fagen, Jonathan Cape, RRP£16.99/Viking, RRP$26.95, 176 pages

As befits a musician who made merry and smart during the golden age of the vinyl album, Donald Fagen, co-founder and frontman of Steely Dan, has split this collection of autobiographical essays into two, violently contrasting, sides. Side One is a delight: reminiscences of a not-especially disturbed adolescence, full of telling detail and recollection of spent passions. Fagen is well-known for a certain urbane smart-arsery in his songwriting that might have disappointed here, but these observations from the 1960s are constantly surprising, and recalled with great elegance.

His little essays-in-tribute to the figures evoked by the book’s title have the sting of emotional authenticity, and are mercifully uninterested in cooler-than-thou poses. In “Henry Mancini’s Anomie Deluxe” (yes, it sounds like a Steely Dan album title), the singer talks of the effect – it was hardly exclusive to him – of seeing Breakfast at Tiffany’s for the first time (“When the venal waif Holly Golightly got out of that cab . . . I wanted to sip her through a straw”).

But he rehabilitates director Blake Edwards and composer Mancini from their reputations as little more than artful squares, arguing that both were masters in exploring the dark side of their seemingly wholesome times. To witness Edwards’s flirtations with danger was “like seeing a smiling Pan Am pilot climb out of his 707 with a copy of La Nausée sticking out of his back pocket”. Mancini in the meantime became almost terminally unhip, only to be rescued in the “irony-saturated eighties”, which gradually tuned with greater earnestness into his deftness with rhythm and melody.

There are lovely appreciations of the Boswell Sisters, cold war paranoia-fuelled science fiction, and the jazz clubs of New York. Fagen’s description of his beginnings as a musician are almost corny in their cinematic quality: what should be playing on the car radio when his father first took him to Bard College than Bob Dylan’s “Like a Rolling Stone” (“I was leaving one world, but hadn’t quite arrived in the next”)?

College life for the Class of ’69 was peopled by little Jewish “firecracker” lecturers, unhinged beauties, and “a severe-looking bespectacled kid . . . playing a cranberry red Epiphone guitar” who would turn out to be Fagen’s musical partner and bandmate for the next 40 years, Walter Becker.

The scene is strikingly set for the story of Steely Dan’s beginnings, but Fagen bails out. There is nothing on the group’s rise to prominence in the 1970s, and nothing on the following decade, when the singer “came apart like a cheap suit”. So we turn suddenly to Side Two of the collection, a diary kept by Fagen during a 2012 tour of the Dukes of September Rhythm Revue, featuring fellow rock veterans Boz Scaggs and Michael McDonald.

The change of tone is abrupt: “Once an insatiable reader, I don’t read so much any more. I’m now at the age – sixty-four – where so many sad things have happened that I’m too broken and anxious to read.” There are some passably amusing grumpy stories about life on the road, but Fagen’s cynicism here becomes a little too world-weary, notwithstanding his talent for one-liners (“As Freud liked to say, the superego is soluble in alcohol.”)

In the entry for July 21, there is a short account of a tragedy suffered by Fagen’s wife, and the smiles are finally wiped off our faces. “Our lives have never been the same, and never will be,” says the author, instantly consigning the overwrought fripperies of rock music to cosmic unimportance. The diary’s final entry is for August 25: “After all the vexation and euphoria of the tour, I was feeling strangely placid, or, perhaps, feeling nothing.” Let’s face it, one of rock music’s most astute practitioners was never going to end on anything other than a minor chord.

Peter Aspden is the FT’s arts writer

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