With post-Dan solo releases being sporadic throughout the ’80s and ’90s — represented solely by Fagen’s The Nightfly (1982) and Kamakiriad (1993) and Becker’s 11 Tracks Of Whack (1994) — their legacy spent two decades slowly being slotted into a classic rock canon they were often at strange odds with. (Ever hear “Reelin’ in the Years” or “Josie” sandwiched between Foreigner and Bob Seger? It’s like a transmission from another planet.) So after spending much of the ’90s touring and reestablishing their history with releases like the box set Citizen Steely Dan, the prospect of a new album was a potentially pretty big deal. In retrospect, though, it only got partway “there” in the popular consciousness. It received decent reviews — decent enough, anyways — and hit a not-disastrous #6 on Billboard’s album charts. But in a year where they were pitted against Gen-X favorites like Beck, Eminem, and Radiohead for Album of the Year Grammy, their win for Two Against Nature still gets held up as one of the most surprising (or, less charitably, “maddening“) wins of all time. Between the skeptical aging fans who felt it didn’t measure up to Aja and the youth-movement poptimists who scarcely cared about a band that last hit the charts when future record-buyers were still in preschool, there were a lot of reasons people turned their noses up at this one.

And yet there’s still something to it: Two Against Nature is a case of an album being delivered by the people who you would most trust to put it out, just at a time when their reintroduction to the mainstream pop world felt strangely out of step. The music industry was still reeling from the artificial high of the pre-filesharing late ’90s, where the tastes of teenagers were dominating the charts more than any time since the peak-Boomer ’60s. So into this fray of Slim Shady dick jokes and Britney Spears provocation come a couple fiftysomething jazz weirdos with an album dominated by songs about sexual derangement. In “Gaslighting Abbie,” a man and the woman he’s cheating with plot to drive the man’s wife insane; “Negative Girl” and “Almost Gothic” are love songs to women whose mood swings and personality crises make them inexplicably appealing; “Cousin Dupree” is lite-incest desperation (and, go figure, the big single). The allusions aren’t quite as sly as they used to be, but the bite hits the bone — when the breeziest, cheeriest thing on the record is “Janie Runaway,” an idealized ode to seducing a missing teenager with the kind of pitch you could imagine Taxi Driver’s Keitel-pimp Sport giving Jodie Foster’s Iris, it’s clear you’re still dealing with some dark comedy venom here.

So maybe the relatively flat production is what helps it pass muster this time around, as opposed to having light ideas left fluttering through the impactless, vague odor that permeates Everything Must Go. The smoother, the creepier, maybe — ironic counterpoints filtered through shiny state-of-the-art Audio Product Refinement, easy listening for uneasy realizations. That doesn’t make the funk-lite fussiness that much more memorable, granted, and for every lead vocal where Fagen makes being broken in the brain sound like the apotheosis of class and refinement over electric pianos you could swim through, there’s this odd sense that all the edges have been filed down just a little too much, like the drums have been run through an autoclave to get rid of any unseemly residue of intensity or drive. Still, it’s fun to think of how many well-intentioned wine-tasting party soundtracks have been turned weird by this record — if not by the deranged plotting of opener “Gaslighting Abbie,” then definitely by “What A Shame About Me,” a strong entry in the great canon of works about Failing in New York: “I said babe you look delicious/And you’re standing very close/But like this is Lower Broadway/And you’re talking to a ghost.”