Song You Need: A Steely Dan grail is a song of the summer contender

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“Third World Man,” the last song on Steely Dan’s 1980 masterpiece Gaucho, is a dank and unsettling thing, a five-minute meditation on post-traumatic stress disorder rife with paranoid delusions and miserable realities. Steve Khan plays a louche guitar that periodically tightens up in staccato angst, and Donald Fagen sounds studiously cold behind his rakish delivery, drawing out the syllables on “Smoky Sunday.” It had been five years since Robert Christgau had written that Steely Dan were “the Grateful Dead of bad vibes.” Here, as the closer to what would be their last album together for two decades, Fagen and Walter Becker seemed intent on living up to that pseudo-compliment.

It wasn’t supposed to end like that, though. Gaucho should have ended with “The Second Arrangement,” a song beloved by the band, producer Gary Katz, and engineer Roger Nichols. It had made it through Steely Dan’s famously torturous studio process (they were such perfectionists by this point that they’d given up on drummers entirely and brought in a proto-drum machine called Wendel), and all the song needed was a layer of horns before it took its rightful place on the album. Instead, completely by accident, a junior engineer wiped the tape pretty much clean when trying to get it ready for playback. All that remained was the fade-out. “The Second Arrangement” was strong enough to survive Gaucho-era Becker and Fagen’s metiulousness once, but it couldn’t muster another round. After trying to re-record and resurrect the song a few times, they decided they’d never recapture the magic of the original.

It became the Holy Grail of Steely Dan outtakes. Over the years, it’s been pieced together by fans using scraps, 30-second demo clips, and sticky tack. But, especially by the standards of a band who cared so much about the way the thing sounded, all of these versions were infuriatingly inadequate, odd little monsters.

And all this while, the original version was just sitting on a cassette in a drawer in Roger Nichols’ house. Nichols was, as Jake Malooley writes in his excellent blog post at Expanding Dan, always bringing home cassette tapes from the studio, and the day “The Second Arrangement” died was no exception. But it never left the drawer until Nichols passed away in 2011 and his daughters, Cimcie and Ashlee, went through their dad’s stuff.

The full story of how the song made it from the drawer to the internet is well worth reading. But while you’re doing that, go ahead and listen to “The Second Arrangement” on repeat like I have been all week. The guitar riff is an all-timer, insistent but a little playful, Steely Dan at their jazz-inclined best. The chorus seems straightforward and classical at first but keeps slipping into unexpected shapes and keys, never quite at ease, a Fagen calling card (he does it masterfully on “Maxine,” from his debut solo album, The Nightfly).

Lyrically, “The Second Arrangement” is far from good vibes and far from shocking — a down-on-his luck, recently-divorced man paying the price for his poor decisions? In a Steely Dan song? Never! — but it’s a long way from murder and monomania as well. In fact, up next to “Third World Man,” it’s a breezy, carefree, song-of-the-summer contender.

"The Second Arrangement" is currently not available on streaming services.

CORRECTION: An earlier version of this article credited Walter Becker as the guitarist on "Third World Man." It was in fact Steve Khan.