Hear Me Out: Steely Dan’s Two Against Nature Deserved Its Grammy Win

Hear Me Out is a column dedicated to earnest reevaluations of those cast-off bits of pop-cultural ephemera that deserve a second look. Whether they’re films, TV series, albums, comedy specials, videogames or even cocktails, Hear Me Out is ready to go to bat for any underappreciated subject.

The 2001 Grammy Awards featured a relatively stacked field of nominees across the board. It was the year that albums like Eminem’s The Marshall Mathers LP, Beck’s Midnite Vultures, Radiohead’s Kid A and Britney Sprears’s Oops!… I Did It Again were recognized, though none of them took home the biggest award of the night: Album of the Year. No, that honor went to Steely Dan. Folks were outraged by the Recording Academy’s decision to give the top Grammy prize to Two Against Nature instead of, by all accounts, two of the best records of its time (The Marshall Mathers LP and Kid A).

And sure, that anger was warranted. But it’s not like Steely Dan weren’t deserving of being in the conversation for Album of the Year in the first place. Before they went on hiatus in 1981, Walter Becker and Donald Fagen enjoyed great critical and commercial success from 1972 to 1980—releasing some of the decade’s best LPs, including Countdown to Ecstasy and Aja. When I think of “definitive” bands from the 1970s, Steely Dan springs to mind often. The back-to-back singles of “Peg” and “Deacon Blues” alone solidify the duo as one of the most crucial rock acts of the era. But when Becker and Fagen were adorned with that coveted Album of the Year nod over the industry’s brightest young musicians, it set off a two-decades-long animosity toward Steely Dan—an overblown overreaction to a systematic choice made by a system that’s long been flawed anyway.

By my measurements, the Grammys only got four of the previous 10 choices for Album of the Year correct. And in the 23 years since Two Against Nature, they’ve made the right pick three, maybe four times. If you’re as chronically online as I am, then you too are well-aware of just how unserious the Grammys have become in the Year of Our Lord, 2024. Given how the Recording Academy has snubbed Beyoncé alone four times for Album of the Year, it’s difficult to really give them the benefit of the doubt these days. Winning Album of the Year isn’t what it once was, when bang-on LPs like Sgt. Pepper’s Lonely Hearts Club Band or Tapestry were walking away with the gramophone without much worry.

Two Against Nature winning when it did, however, signaled something much deeper than Kid A or The Marshall Mathers LP getting snubbed—it was as if the music industry’s leaders had yet to catch on to what anyone born after 1965 was listening to. Paste contributor Zach Schonfeld called Steely Dan’s win a “revenge of the [baby] boomers” and he’s spot on with that sentiment. When we are growing up, we’re—for some reason—conditioned to believe that the Grammy Awards are the end-all, be-all pinnacle of the music world. You might have made one of the greatest records of all time, but if you aren’t walking off the stage with that Album of the Year trophy, that greatness means nothing, etc. When the 2001 Grammys took place, we weren’t even two years removed from the infamous catastrophe at Woodstock ‘99. The disaffected youth of Y2K were still just as disaffected, and two men singing about middle-aged alienation and forlorn love didn’t align with the main demographics of modern music success.

Steely Dan had been nominated for Album of the Year twice before 2001: in 1978 for Aja and in 1982 for Gaucho. They lost both awards—and, while Fleetwood Mac’s Rumours absolutely deserved to beat the former, I’d argue Becker and Fagen should have won for Gaucho instead of John Lennon and Yoko Ono for Double Fantasy. Looking at the five nominees for the award in 2001 is like watching two generations clash head-on: Steely Dan and Paul Simon represented the legacy selections, while Eminem, Radiohead and Beck were the new kids on the scene. The Grammys not including a female artist in the category would require a separate essay, but I’d be remiss if I didn’t note that Britney Spears, Madonna and Fiona Apple were overlooked here (and you could make an argument that When the Pawn… was the best album nominated that night across the board).

2001 was also the Grammys year where Eminem and Elton John famously performed “Stan” together amid the accusations of homophobia being thrown onto the former—and that performance alone is what remains the most remembered part of the entire ceremony. I think The Marshall Mathers LP is a great rap record, probably one of the most essential genre releases of the 2000s when the decade was all said and done. While it being nominated for Album of the Year at all still remains a shock to me, I don’t see a world where a project featuring a song like “Kim” gets awarded the most prestigious industry brass (but, then again, “Cousin Dupree” won Best Pop Performance by Duo or Group with Vocal, so what the hell do I know?). The Grammys play it safe, and them nominating Eminem’s third album in the first place was their one step toward risk (see 2003, too, when Eminem would lose to Norah Jones). My personal favorite album that was nominated for the award was Beck’s Midnite Vultures, which I still consider to be his greatest full project ever (sorry Odelay fans). It was his fusion of funk, R&B, rock and disco, and it was terrific—though it didn’t have quite the commercial success that Odelay had three years earlier. When I listen to Midnite Vultures, I never think “this is a Grammy winner.” It just doesn’t have that industry-flavored juice that, as bland as it is, is a requisite for most Album of the Year triumphs.

If you look at the last 25 Album of the Year winners, practically none of them stand out for being a “risky pick.” The closest one that fits that arc, for me, would be Billie Eilish’s When We All Fall Asleep, Where Do We Go?, which isn’t even that odd of a choice—it just doesn’t have the cookie-cutter pop trademarks that its fellow nominees, like Lizzo’s Cuz I Love You and Ariana Grande’s Thank U, Next, did. And even then, the Grammys could have gone even more off the wall by selecting Lana Del Rey’s much better Norman Fucking Rockwell! for the award. A record as controversial as The Marshall Mathers LP or a record with the experimental playground of Midnite Vultures was never going to break through the Recording Academy’s vanilla mold.

So that leaves us with a one-versus-one of the ages: Steely Dan’s Two Against Nature versus Radiohead’s Kid A. On paper and in practice, Kid A is the better album. I am not a Radiohead fan by any means, save for a song here and a song there, but even I wouldn’t dare say that Kid A is somehow lesser than Two Against Nature. Just three years prior, Radiohead’s OK Computer—a record largely considered to be one of the greatest records of all time—lost to Bob Dylan’s Time Out of Mind. Surely one of the most renowned rock bands of the last 30 years couldn’t possibly lose Album of the Year twice in three years to artists’ “comeback” albums? Well, luck was not on Thom Yorke, Ed O’Brien, Philip Selway and Jonny and Colin Greenwood’s side.

But the question of “Did Steely Dan deserve to beat Radiohead?” lingers on 23 years later, and it’s usually met with a swift “no.” But what I’m arguing has nothing to do with whether or not Walter Becker and Donald Fagen should have beaten Radiohead. Instead, all I am saying is that they deserved their Album of the Year win. Who they beat to earn it really doesn’t matter at the end of the day. Did Steely Dan deserve to win an Album of the Year award at some point? Yes, even though Two Against Nature is Steely Dan’s eighth-best album (they’ve only released nine in total)—as opposed to how Kid A is probably Radiohead’s second or third-best album (the ranking hinges on your opinion on In Rainbows, which would lose in 2009 to Robert Plant and Alison Krauss’s Raising Sand, in case you needed another reason to be mad at the Grammys).

If Two Against Nature had won the award in, say, 2003 when the competition would have been Norah Jones (Come Away with Me), Eminem (The Eminem Show), Dixie Chicks (Home), Nelly (Nellyville) and Bruce Springsteen (The Rising), the deck wouldn’t nearly have been as stacked against our yacht-rock sleaze heroes. But when a record with a “greatest of all time” consensus like Kid A is in the conversation, well, it’s hard to argue in favor of Steely Dan. But, I’d like to offer one nugget of thought: The Grammys have never had a reputation for consistently awarding its most coveted prize to the greatest albums of all time. By my count, here are the records that fall into that category that did win Album of the Year: Songs in the Key of Life, Sgt. Pepper’s Lonely Hearts Club Band, Rumours, Tapestry, The Miseducation of Lauryn Hill, Bridge Over Troubled Water and Graceland. 66 albums have won the award; seven of them being all-timers isn’t necessarily an impressive winning percentage.

I think of Two Against Nature’s win in the same way I think of Leonardo DiCaprio’s Best Actor win for The Revenant in 2016—in that they’re both “sorry it took us so long to give you this” wins. DiCaprio, ever the generational thespian, should have won for The Aviator in 2005, and the Academy likely saw how weird it was that one of the most lauded living actors had not yet won the most coveted award in acting. Steely Dan should have won for Gaucho in 1982, and it probably looked bad to somebody that the duo had been nominated nine times between 1975 and 1982 and been shut out completely. But unlike DiCaprio, who has cranked out films consistently since the early 1990s, Steely Dan hadn’t made a record together in almost 20 years prior to Two Against Nature; the record was a symbolic return of two greats as much as it was a continuation of their pretty damn good discography. And let’s be real, we were all really stoked that DiCaprio won in 2016, even if we can all admit that The Revenant was not that solid of a flick.

The Grammys are also suckers for awarding an album their top prize if said album has a juicy story pinned to it. In 2005, Ray Charles’s final studio LP won; Eric Clapton’s Unplugged, which featured the tragic “Tears in Heaven” took home the award in 1993; The Concert for Bangladesh, a compilation of the performances from the titular, groundbreaking charity event, nabbed the win in 1973; Simon & Garfunkel’s final album together won in 1971. I don’t blame the Recording Academy for seeing Steely Dan’s comeback and adorning it with an award that, if we’re going strictly off of quality and impact, should have gone to Radiohead. But the Grammy Awards are never going give a band like Radiohead its due, unless they break up and then drop an album 20 years later.

Kid A, as undecorated by primetime television award ceremonies as it is, remains beloved. Pitchfork gave it a 10/10 (as opposed to their 1.6/10 review of Two Against Nature) and Rolling Stone gave it four out of five stars when it came out (they awarded Two Against Nature three-and-a-half stars), and music fans far and wide saw its omission in our recent greatest albums of all time list as a blunder. Radiohead has a cultural staying power that does not hinge on institutional credibility. Sure, Kid A winning Album of the Year would have meant that Yorke and Greenwood’s compelling vision was given its hard-earned due. But Radiohead doesn’t need the Grammy Awards.

And, oddly enough, Steely Dan did? Becker and Fagen’s work always existed on the fringes—the music was satirical, witty, technically precise and complicated, but a piece was missing somewhere. They were critically and commercially adored, yet never rewarded with shiny trophies for their efforts. Their propensity for multi-dimensional, orchestral approaches to jazz fusion and blistering rock ‘n’ roll seems just a touch too delicious for music’s biggest night, and perhaps odd, ordinary, offbeat, slimy and otherwise cringey character studies weren’t the right material for the Grammys—maybe had they written a breakup album or some soft-rock radio fodder they’d have been legitimate to the suits 45, 50 years ago. If Eagles couldn’t puncture the Recording Academy, Steely Dan sure as hell weren’t going to.

Two Against Nature is a unique case, though, as it’s the album that cemented Steely Dan’s critical legacy and cemented their cultural loathing. The widespread hatred for the band did not exist then like it does now, and you can thank the Grammy Awards for that sea change. While few rock acts in music history have ever had a late-career renaissance quite like Steely Dan’s, the kids of 2001 were not much interested in songs about hotel rendezvous and problematic family members, nor did they care to embrace the remnants of the yacht rock their parents listened to 20, 30 years prior. But Two Against Nature is a good album that picks up right where Gaucho had left off. After disbanding in 1981 and reuniting in 1993, Steely Dan took seven years to hone their bedrock. The jazz-rock amalgams are crisp, Fagen’s voice sounds as legible as ever and their characters admonish sentimentality for sometimes-uncomfortable deep, personal reflections and depictions of awkward, out-of-place love and alienation.

“What a Shame About Me,” “Jack of Speed,” “Cousin Dupree” and “West of Hollywood” are some of Steely Dan’s best tracks ever, and Two Against Nature is the kind of record that could have only been made by two bandmates who’d seen the top of the mountain together, took some time away from each other and then, when the world had moved far away from them, reunited to reconsider the magnitude and fallout of it all. If we take away the on-paper blunder of Two Against Nature beating Kid A and remember that the Grammys are not the tastemakers we’ve been conditioned to believe them to be, it’s hard to not buy into the compelling, underdog narrative Steely Dan had so expertly (and, perhaps, unintentionally) fallen into by the turn of the millennium. After going 0-9 at the Grammys before 2001, Walter Becker and Donald Fagen had ditched their “Deacon Blues” identity and found that Crimson Tide glory after all. “I’m way deep into nothing special,” indeed.