When Chuck Berry died a couple weeks ago, we lost a giant of rock ‘n’ roll, a man whose existence had arguably more impact on this list of 500 albums than anyone, living or dead. This is not really an argument so much as a basic tenet of rock music writing, one that’s been affirmed in the chorus of praise since his death. “Chuck Berry was to rock music what Louis Armstrong was to jazz—a foundational figure; if not quite singular, then as close as it gets.” That’s David Remnick, writing in The New Yorker, but you could look to any of the white, male zombies of rock writing—Robert Christgau, Jon Parales—for more of the same. In a piece published last spring, Chuck Klosterman declared Berry the John Philip Sousa of rock ‘n’ roll. Three hundred years from now, Klosterman argued, it would be Berry’s name—not Elvis’s, not Dylan’s, not the Beatles—that historians would associate with the genre, the way Sousa looms singularly over American marching music. Whether there’s any merit to this opinion is not my concern (if that’s what you’re interested in, I would steer you toward the comments section of that article). I only bring it up as a sad point of contrast: around 2009, when Chuck Berry was still very much alive and well, I had barely any understanding of who he was.

My ignorance first surfaced in the office of my college newspaper, where, believe it or not, I wrote about music for the arts and entertainment section. It was late and I was struggling to describe a campus band on a deadline, when I found Chuck Berry’s name under the influences section of their Myspace page, of all places. Without bothering to listen to even a snippet of a YouTube clip, I described the band’s music as “Chuck-Berry-channeling-madness,” and hit submit. Sad, I know. What I thought I was gaining by affecting a familiarity with art I was not at all familiar with, is a good question. Rest assured that, if there’s any cosmic justice, I will spend my next life as a roadie for Hoobastank.

A few years later, I was waiting for some hash browns to fry up, when a roommate put on a copy of Chuck Berry’s Greatest Hits. More specifically he put on “Johnny B. Goode,” the same recording that Carl Sagan preserved on the Golden Record aboard Voyager 1, currently the farthest human object from Earth, barreling into deep space at speeds of 17 kilometers. In the implausible scenario that aliens recover this record (and have ears and appendages and the patience to sit through a Senegalese drum circle, a Bach concerto, and a Pygmy initiation chant), they will hear a defining document of American rock ‘n’ roll, one that I didn’t know until I was 20. My first reaction was a shock of recognition. This was Chuck Berry? He sounded like the guy who did that Christmas song about Rudolph. I think I said something to that effect aloud. My roommate just stared at me, without blinking. My second thought was that yeah, that college band did sort of sound like this. Which they did of course; every rock ‘n’ roll band sounds at least a little like that.

Well, almost every rock ‘n’ roll band. While Keith Richards was studying every inflection of Chuck Berry’s guitar, Donald Fagan was lying awake in suburban New Jersey, scanning the dial for jazz, standards, and vocal groups. Mostly he was drawn to black piano players: Ray Charles, Duke Ellington, and the giants of Harlem stride piano—guys like Earl Hines, James P. Johnson, and Willie “the Lion” Smith. In his memoir/tour diary Eminent Hipsters, Fagan credits his mother, a jazz singer, for introducing him to the Boswell Sisters, a New Orleans vocal trio whose subversive chord changes and emotionally ironic singing style (a style he describes as both “hot and cool”) made a deep impression on him. An early love of Harry Mancini, the composer of classic Hollywood schmaltz like “Days of Wine and Roses” and “The Pink Panther,” turned him onto jazz music. By his teens, he was accompanying his older cousin to jazz clubs in the city, where they saw Mingus and Coltrane. Among a sea of folk-rock hippies at Bard, he bonded with Walter Becker over their shared love of Miles Davis. The two started writing demos together with funky grooves, jazz chords, absurdist lyrics, and names like “Barrytown” and “Brooklyn (Owes the Charmer Under Me)”.

After leaving Bard, Becker and Fagan abandoned their collegiate material in favor of commercial pop music. They spent some time peddling tunes to Tin Pan Alley. They co-wrote “I Mean to Shine,” a largely forgotten Barbara Streisand single. They played in the touring rhythm section of Jay and the Americans, an early boy-band forerunner, known for their nostalgia-laced throwbacks to the ‘50s. By 1972, just three years out of college, they’d had enough of that. They decamped to the West Coast, where, with the aid of producer Gary Katz, they returned to their experimental college demos. They rotated through a cast of hot-dog session players, searching for musicians that could navigate the complex arrangements. Unsatisfied with what they heard, they decided to tone down the jazz stuff in favor of radio-friendly rock tropes. Those recordings became Can’t Buy a Thrill; Becker, Fagan, and the expansive roster of studio musicians in the liner notes became Steely Dan.

Nowadays, Becker and Fagan disavow Can’t Buy a Thrill as a minor work, a stepping stone to the records that came later. Certainly, it’s the only album-length concession they made to rock music of the Chuck-Berry-channeling variety. They keep the jazzy interludes and the hokey changes to a minimum. The solos they do include (classics like Elliot Randall’s on “Reelin in the Years” and Jeff Baxter’s on “Change of the Guard) feature mostly guitars. Lyrically, I never know what Fagan is going on about, but at least on this record, he doesn’t ruin a great melody with a line about a girl turning 18. To call any Steely Dan record emotional or heartfelt is nuts, but compared to the later records, Can’t Buy a Thrill has some seriously touching moments: the chorus of “Turn That Heartbeat Over Again”; that high, lonesome steel guitar on “Brooklyn (Owes the Charmer Under Me)”; the minor key strut of “Only a Fool Would Say That”. Not that Can’t Buy a Thrill doesn’t sound like a Steely Dan record. A pianist and a bassist respectively, Fagan and Becker remain one of the most idiosyncratic songwriting duos in rock history. They never wrote a song that didn’t sound like them, even when it was sung by Barbara Streisand.

For what it’s worth, Can’t Buy a Thrill is my favorite Steely Dan album, the only one I enjoy listening to front to back. There’s a wistful quality to it, a soft Latin soul, that goes missing as they progress toward the funked-up elevator Muzak of Aja. With a few songs excepted (“My Old School,” “Barrytown,” Peg,” and maybe “Bad Sneakers”), I could do without their subsequent records entirely.

My personal tastes aside though, I love the wedge that their work, taken as a whole, sledgehammers into our generational understanding of taste. In his RS500 piece on Pretzel Logic, Steven Casimer Kowalski touches on this: “Imagine your parents, imagine your mother and father, imagine them existing in infinite universes and then find the most embarrassing pair of the bunch. Those two are huge Steely Dan fans.” I would add that what makes Steely Dan parent-fans more embarrassing than, say, Huey Lewis or Journey parent-fans, is their disdain for convention. The conventional narrative around baby-boomer rock begins with black blues guitarists and runs through Berry, Elvis and the Beatles/Stones. By reaching around Berry to steal from black jazz pianists, and by elevating Hollywood cheesemongers like Mancini to the counterculture, Steely Dan twist that narrative a little.

In my family, taste in music is very much a generational thing. My record collection, which grew from my parents’ and my grandmother’s records, reflects this. Going back one generation are the Rolling Stone-approved records my parents loved, the ones I grew up with: Dylan, Fleetwood Mac, the Beatles, E.L.O. Going back another, are the jazz and standards that my grandmother loved: Stan Getz, Herbie Mann, and Mancini movie soundtracks—the kind of thing that Rolling Stone wouldn’t touch. For most of my life, I’ve written my grandmother’s taste off as boring and middle-brow, the mid-20th century equivalent of liking Dave Matthews Band and the Goo Goo Dolls. Once again, I was assuming some level of familiarity with art I was not at all familiar with—worse, I was passing critical judgment on it. Lately, I’ve been going through my grandmother’s records, trying to remedy that. Along the way, I’ve fallen hard for Dave Brubeck and Bill Evans. I’ve learned that Stan Getz isn’t always terrible. But the music that’s floored me most is probably Mancini’s. Specifically “Moon River” (the Audrey Hepburn version, from the Breakfast at Tiffany’s soundtrack.) I’d never heard it. It’s a stunning song, a musical landmark that, like Chuck Berry, went from cultural ubiquity to outside my orbit in the span of only two generations. At their best, this is what Steely Dan does well: they get disparate corners of our vast culture to co-inhabit a three-minute pop song.

At their worst, Steely Dan is an affront to everything that rock music stands for. The recordings are too smooth. The lyrics are too cerebral. The songs are too fussy, the melodies too overwrought, the solos too self-indulgent. They’re too something, I want to say, in a French accent, while making a cartoonishly effete gesture with my thumb and forefinger. The most articulate critic I’ve read on the subject is William Burroughs, who was introduced to Steely Dan’s music in a 1977 interview with the now-defunct New Times Magazine. Burroughs, who claims not to know that a dildo in his book Naked Lunch inspired the band’s name, is unimpressed with the snippet of “Black Friday” he hears. “These people are too sophisticated,” he says. “They’re doing too many things at once.” He goes on, comparing the band’s efforts to literary success. “To write a bestseller, you can’t have too much going on. You take The Godfather, the horse’s head. That’s great. But you can’t have a horse’s head on every page. These people tend to have too many horses’ heads.”

If we can put aside the irony of Burroughs criticizing anyone for artistic over-indulgence, I want to dwell for a moment on the connection he draws between music and writing. No doubt you’ve heard that exhausted line, credited to everyone from Nietzsche to Elvis Costello, comparing writing about music to dancing about architecture. I hate this line. While it’s true that writing packs only a sliver of the emotional wallop that music can dole out, the two art forms have had a lot to say to each other over the years, even before Dylan won a Nobel. I can’t listen to Astral Weeks and not hear Lester Bang’s words in my head; if not for Peter Guralnick’s writing, names like Rufus Thomas, Ernest Tubb, and Sleepy LaBeef wouldn’t mean a thing to me. I can still rattle off the names of the Pitchfork writers who wrote about Sigur Ros, Broken Social Scene, and Animal Collective when I was in college.

What draws us to write about music? What compels us to read what others have written? In an era when the entire history of recorded music is at our disposal, why read about music at all? I don’t have good answers to these questions. Certainly, there are times, especially while struggling with a piece of music writing, when these answers devolve into wishing I’d read less as a kid and picked up a guitar instead. Confronted with an unwieldy paragraph, or a thought that won’t arrange itself into a sentence, I roll my desk chair over to the corner of my room and start noodling around on a guitar. I don’t really know chords, or songs, but I keep the thing in open tuning, so it doesn’t really matter. I pick around until I find a succession of notes that sound interesting and then I play them over and over, until the writing impulse returns or my roommates ask me politely to stop. I have no active interest in getting better at guitar; there’s just something about the immediacy of producing sound that is addictively different from the hard-wrung pleasures of producing written thought. The two arts complement each other in a strange way I’m struggling to articulate. I’ll defer to the late, great Guy Davenport: “Music is as close as we will get to angelic discourse,” he wrote in his essay “On Reading”. “Literature comes next, with a greater measure than music can claim of the fully human.”

One weird paradox of writing is that the amount of work I put into a piece tends to correspond inversely with the amount of work required to read it. This particular piece went through about five drafts. In my experience, that’s a healthy number. The horse heads don’t tend to rear up, if they rear up at all, until around the third or fourth draft. I’m not sure this paradox holds true for recording music. For better or worse, though, this is the Steely Dan approach to making a record. A quick listen to those early college demos reveals how much their music benefited from revision. There isn’t a note on Can’t Buy a Thrill, their sloppiest record by a mile, that sounds unconsidered or out of place. Whether this is the kind of perfection that belongs on a rock record is a question for the ages. But it’s only in the pursuit of some unattainable ideal—whether it’s an insane degree of sonic fidelity, or the more perfect crystallization of human thought—that you get that rich sense of loss, that heavy measure of the fully human.

—Ryan Marr