Let’s say it doesn’t work out. You cross over from adolescence to adulthood and wind up living a life you didn’t choose. The rooms are depressing and fluorescent; the people who once offered comfort grow distant; any ambition for the future is replaced with a somewhat nauseating impulse just to get through the day.

David Berman sings to one such person in “Pretty Eyes,” at the very end of The Natural Bridge, an album he made when he was 29. His friends and collaborators in Pavement were achieving a type of success that must have seemed like a dream back when he and Stephen Malkmus first met as students at the University of Virginia. Pavement had something that could conceivably be called a hit single; their videos were in frequent rotation on MTV; they were reaching the masses from festival stages and rave reviews. Meanwhile, Berman had been living in Amherst to study under the tutelage of his hero, the poet James Tate. “To do that, I got into this MFA program,” he told Frequency Magazine in 1999, “and found out I could go up there for three years and not work. It was great.”

After several failed attempts at making a second record—the follow-up to 1994’s Starlite Walker, a shaggy, lovable album he made with Malkmus, Bob Nastanovich, and Steve West—he got together with some local musician friends in Massachusetts. At the end of the sessions, they watched as he strummed through “Pretty Eyes,” sleep-deprived and hell-bent on getting it all right in one take. In the opening verse, he sings these words:

I can see you in your room at night
The pictures on your walls
Little forest scenes and high school Halloweens
But they don’t come to you
They don’t come to you at all

As far as Silver Jews lyrics go, these ones are fairly straightforward. He sings in the second person to someone he can access only in his mind. He recognizes they are at a stage in life when their escapist fantasies and childhood memories are equally out of grasp, more useful for locating the pains of the present. He offers this song—which ends on the romantic promise of “I’ll always remember your pretty eyes”—as a means of consolation and farewell.

This particular bedroom isn’t the only place where The Natural Bridge grants us access. There’s a barroom where a lonely man avoids his reflection in the mirror; an abandoned drive-in theater with ivy growing over the screen. Nearly every setting on The Natural Bridge illustrates his worldview through some sense of deterioration. The scenery is always dripping and creaking; people are shaking and shivering; the perspective is grayscale and bleak. While recording the album, Berman felt haunted by the graveyards of Massachusetts and a truck parked outside the recording studio, a former gun factory, bearing initials that spelled out “G.O.D.” Listen closely and you might start seeing God, too.

“Liking The Natural Bridge is liking me at my ostensible worst,” Berman said in one of his final interviews. He died in 2019, leaving behind a catalog with no real weak points, so the “worst” in his assessment seems less about the quality of the work than his state of mind: the first time in his career when his art seemed beamed from some desolate terrain that he could not escape. Due to the tragic circumstances of his life and a mythology he couldn’t help but spur on (“I always loved bands with mystique,” he confessed), this burnt-out mood is probably the closest to how people remember his music. Even when he’s telling jokes, resisting sentimentality to the point of abandoning meaning at all, his questions are naked and troubling and unignorable.

Much of the brilliance of Berman’s work gets boiled down to his writing, but The Natural Bridge is a memorably atmospheric record—the types of songs you return to both for what they express and how they make you feel. Even beyond the melodies, this is an album full of texture. Just as you could spend an entire essay running through the lyric sheet, there are almost too many sonic moments to list. The way the snare drum harrumphs uninvited into “How to Rent a Room.” The muted soft-rock piano of “Dallas” that sits atop the arrangement like a stubborn layer of snow on a rooftop. The whip of white noise as he sings about the death of a pet in “Pet Politics” or the gorgeous ripple of acoustic guitar and piano that kickstarts his verse about the Bible a minute later.

Backed by members of the Amherst band New Radiant Storm King, Berman introduced a lineup of Silver Jews that existed for only one record. (They did not tour the album, and, as far as I know, there are no outtakes.) This was the only band who seemingly aspired to Spiderland as much as Beggars Banquet, and they were the most tethered to the therapeutic nature of his writing process. “Almost everyone I’ve told that it was a sad record said it doesn’t sound sad at all,” he observed to The Independent upon release. “I think recording was a process of calming myself down, and it might come across that way.”

Part of what the album teaches is patience, an invitation to carry the art into the world and see how the passing of time affects your understanding. Maybe one day you will hear “Bring It on Home to Me” on the radio and notice the line that Berman inverts in “How to Rent a Room” (“I know you laughed when I left/But you only really hurt yourself”), putting its narrator in conversation with Sam Cooke from the other side of the door. These connections are even designed into the packaging, like the quote from the Gospel of Thomas printed on the record label in reverse, so fans would have to hold it to a mirror to read it. The idea is to catch your own reflection, to recognize yourself, to notice how much we overlook every day.

This level of intimacy may be why the people who love Silver Jews tend to really love Silver Jews. And the people who love this record tend to really love this record. “There’s two kinds of Silver Jews fans,” Berman once said, “the ones who favor The Natural Bridge and the others.” Where other career staples like American Water offer a greater sense of melodic uplift, Tanglewood Numbers presents a more energized band, and even Purple Mountains extends his universe with warmer, richer arrangements, The Natural Bridge is as direct and unflinching as his music ever sounded.

In an indispensable piece of reporting for Stereogum, in 2016, Ryan H. Walsh detailed the process of bringing this album, tirelessly, to life. Here, you get all the details you could want about the album’s creation. There were the aborted sessions with Scud Mountain Boys, the alt-country band led by Joe Pernice, another songwriter who obtained a poetry MFA at Amherst. There were the planned sessions with Malkmus, Nastonovich, and West, which Berman flaked on, thus giving Pavement studio time to make what would become the Pacific Trim EP.

Once the record finally got set in motion, there are mythical stories of Berman instructing his bandmates to match his frayed, sleepless state of mind (“He urged me to play like my feet were sopping wet,” recalled guitarist Peyton Pinkerton) and speaking at length about each song to help them embody the words. There’s a scene of him lying behind the drum set, writhing in “psychic agony,” before delivering his vocals. There’s the sense, once the record is released, that it failed to justify the great lengths he and his collaborators went through to make it, not to mention the hype afforded to him by his proximity to Pavement. “I thought I’d made a terrible mistake,” Berman said of the immediate aftermath.

But what exactly did he want to gain from this music? After all, so much of his writing exists to document the sad fixtures who live just outside the spotlight: the other house in New Orleans that didn’t make the cut in “The House of the Rising Sun,” the other guy in the Garden of Eden whom Adam killed before he could develop a storyline. His most iconic lyric involves “approaching perfection,” and even that he describes as something akin to sickness. “I make art out of hostility,” he confessed to The Guardian in 2002. “I started writing poems because I wanted to make poems so good they would make everyone else quit. I don’t have the voice or the technical skills to blow people away with my music.”

There is some truth to this statement. In 1999, Actual Air, the extraordinary result of Berman’s MFA thesis, would garner praise from poet laureate Billy Collins, formative influences like James Tate, and even a glowing review in The New York Times. These are mainstream accolades that it’s difficult to imagine being granted to even the most accessible Silver Jews album at the time. And yet, so much of Berman’s art encourages us not to seek this type of validation. Even that Times critic reviewing Actual Air had to admit he sometimes had no clue what was going on. Using a metaphor from Berman’s poem called “The Moon”—where a man who buys a car, part-by-part, is thrilled to receive an ashtray and wheel in the mail—David Kirby writes that Berman’s more impressionistic writing merely “present the reader with a jumble of shiny pieces that don’t necessarily add up to a whole car.”

Where Berman’s poems might ask us to fill in the blanks, The Natural Bridge shows the crucial way his music could add to our understanding. Take a line like this: “Time, cum, sand, and surf/These are the building blocks of life.” As it appears in the lyric sheet, you might imagine someone misremembering a Jimmy Buffett song with a smirk. But in “The Frontier Index,” the band accompanies this line with claustrophobic, post-punk momentum, as Berman repeats the word “building” with a stutter, his delivery cavernous and steely, like this may be the last wisdom he’ll be able to impart. And so what if it is? Could any other last words be more profound?

Maybe Berman’s tense relationship with this record was due to this urgency. He spoke about how difficult it was to listen to any music after its completion, both because of the intensity of the recording and the strange anticlimax of its arrival. But there is also an exhaustive feeling to the music. From hints of the ’80s goth sound that made him first fall in love with music (among the sole recordings from the aborted Scud Mountain Boy sessions was an Echo and the Bunnymen cover that has allegedly since been destroyed) to deeper dives into the classic country that would define his later work, each song attempts to expand the definition of what a Silver Jews song could be. Say what you want about his drawling, affectless vocal delivery or the hopeless nature of his writing. But you can’t say he wasn’t trying.

Which, as so often in the adult world, leads to disappointment. Hence “Ballad of Reverend War Character,” whose lyrics consist almost entirely of brief, morbid character studies, zooming through entire lives as if skimming through the obits and skipping to the endings. In lieu of a chorus, he offers little pearls of wisdom after each verse. “In a horror movie when the car won’t start/You give it one last try,” goes one, returning to the feeling of terror that courses through the record. Another: “In space there is no center/We’re always off to the side.”

I’ve returned to this lyric many times, and I am always astounded by how much it conveys in so few words. There’s the rebuttal of a cliché—not only are we not the center of the universe, but there is no center at all. There’s also a seemingly teachable lesson, a way to ponder our insignificance that feels so particularly Berman that I imagine nobody else in the world could identify whether it was a source of comfort or anxiety to him. “Well, don’t believe in people who say it’s all been done/They have time to talk because their race is run,” he sang on 1994’s “Advice to the Graduate,” and here was his impetus for moving forward: to keep learning, to say something true.

At the very least, he was able to find a definition of success far from the goalposts he was raised with in Dallas. In a 1999 interview, he talks about the grim view of corporate adult life afforded to him by visits to his father’s notorious work in government affairs and PR. These characters and images would drift through his writing forever: the frosted bank glass, the buildings made of mirrors. “He put the fear into me early on… that I would live a life inside of those worlds,” Berman explains, “and I’ve been able to escape it so far… It’s a terrifying world.”

Maybe this is the world where the character in “Pretty Eyes” lives. Maybe it’s where the guy in “Inside the Golden Days of Missing You” is coming from before he gets to the bar. Maybe it’s what the narrator of “How to Rent a Room” is running from, imagining his death in the eyes of the people he once knew. In the following decade, Berman would find true love and religion, release an influential collection of poetry and several more beloved records, tour the world and meet people who found comfort and meaning in his work. Things, of course, would also get bad. But he tried to strike a balance. “There’s been moments where I felt aging was a process of decay,” he told Dolomite Magazine in 1999, “but the last few years have been the best of my life, and it seems to get better.” The Natural Bridge, in its stark and defenseless way, looks to the future with resistance and desperation. It awakens with a sense that life has begun.