As the ’70s drew to a close, it looked like Steely Dan were in a breakneck race with Fleetwood Mac to see whose followup to a massive ’77 blockbuster would wind up more star-crossed. While the Mac finally got their million-dollar new wave-ish double LP opus Tusk out to a somewhat less receptive public before the decade rolled over, Gaucho was born out of a cavalcade of misfortunes that ground Steely Dan’s album-a-year proficiency into debris and saw them limp defeated into the soon-inhospitable ’80s. To many people, including the band members themselves, Gaucho is a what-could’ve-been story: so many lost opportunities, rumored and hinted at but only surfacing decades later on muddy bootlegs, the final product on record store shelves more of a salvage job than an original vision. Massively overbudget, wracked with technical nightmares and health-jeopardizing accidents, held up in label-rights limbo, and delayed far beyond the point of belief, its labor pains were eerily reminiscent of the last throes of New Hollywood’s auteurist freedom before focus-grouped blockbusters took the reins again.

That said, Apocalypse Now is a hell of a film, ain’t it? Gaucho is in that same ballpark, success-wise and (mostly) critically, a work of art that only sounds like it took forever in terms of meticulousness. Even after losing a pivotal song, “The Second Arrangement,” to an assistant engineer’s tape-erasing screwup, even after subsequently scrapping, possibly out of sheer spite, a handful of additional songs that could’ve been certified Aja-mode classics (“The Bear” and its Isleys-gone-beatnik eeriness is a stunner), even after Walter Becker endured both the overdose death of his girlfriend and injuries from getting hit by a car that left him on crutches, even after MCA used their upper hand in the contract dispute as an excuse to bump the LP’s price to a dollar higher than the rest of the label’s catalog… even after all that, Gaucho wound up worth the turmoil, at least for listeners. It also tore Becker and Fagen apart as songwriting partners, but ending — at least temporarily — on a top 10 platinum record with at least a few fan-favorite songs is a strong way to go out.

And it does sound like the end of something, whether or not the whole ordeal shut the doors on the band as a going concern. Gaucho is the self-aware aging hipster’s reckoning with the decline of Boomer cool; where Tusk flirted with New Wave, “Babylon Sisters” and “Hey Nineteen” and “My Rival” and “Glamour Profession” try to find rejuvenation in meaningless flings, in other peoples’ youth (“Hey Nineteen”), in wounded, shamed revenge (“My Rival”), in the cool-by-association of being a dealer to the stars (“Glamour Profession”). So from the words on down, everything on this record throbs with cumulative uncertainty: will the session players flown in to Manhattan from L.A. be the same 40-take workhorses, or will their coke-naut adventures knock them out of joint? Should the Dan just give in to using a tricked-out, super-sophisticated drum machine for the humanly impossible fills, offering it a real-live-boy name (“Wendel”) so MCA can whimsically award it its own platinum plaque? How long will it take to get that “Babylon Sisters” fadeout just right in the mix? There are only seven corners of this faded, damaged corner of modern-man panic to visit here, but whether it’s rictus-grinningly upbeat (smudgelessly shiny demi-disco on “Glamour Profession”) or a white-knuckled slow jam (“Third World Man” is like finding euphoria by drowning in a jacuzzi), the cumulative effect is devastating.