As I was coming to worldly consciousness in the hick town of Belton, Missouri, a friend slipped me a copy of Fevers and Mirrors by Bright Eyes. I didn't need much time to get used to the singer's voice. Conor Oberst sounded the way I'd have sounded if I had tried to sing. And he was saying everything I didn't know I knew: The suburbs suck, depression is real, religion is empty, we're all going to die, everyone is fake (especially me), and love is our only hope. Such assertions were rare in a town where Revelations was Gospel.

It's easy to laugh about all this now, but I was rage-crying about it then. And it wasn't just the washed-out hair gel from the death of my pop-punk phase stinging my eyes. I was a wannabe intellectual and romantic aesthete in a town where all roads lead to the mall. There was no way out.

Oberst was a test case. A Midwestern emissary out there where the TV said life was. If this guy could make it, maybe we could, too. Maybe we weren't just flyover.

These and a thousand other Midwestern thoughts flooded me while revisiting Oberst's body of work, newly released in a set of remastered studio albums from 2000–2011, and his brand-new solo album, Ruminations. My editor suggested that the only proper way for me to do this story was to sit in my room and listen to all six and a half hours of this music, chronologically, in a single sitting. No friends, no phone, no distractions. Besides an immaculately clean apartment, the critical exercise gave me some welcome perspective.

I had buried a lot of basement days in Oberst's albums, but listening to the songs now, I can see a major part of my enjoyment was the sense of community and friendship he projects on his records.

Oberst and longtime producer/bandmate Mike Mogis always included in the recordings lots of little homey sounds: squeaky screen doors, dogs barking, and other Midwestern atmospherics. The band seemed to be making music no differently than my high-school friends were making music—in some half-carpeted basement studio with the TV on mute, cases of MGD cooling out in the garage.

You can hear a real sense of camaraderie in those ragtag orchestra pieces and in every reference to "Tim" (Kasher, of the Good Life and Cursive) or "Michael" or "my brother." This music was alive with genuine-seeming fellowship based in shared, humanitarian interests and ideas! Close friendship with people who liked this music provided the emotional and intellectual support I needed to get by, and, to the outside observer, that same force seemed to drive those Bright Eyes records.

Also, with the exception of Fevers and Mirrors and maybe I'm Wide Awake, It's Morning, Bright Eyes wasn't really bedroom music. The ghostly westerns, the Opry sing-alongs—most of the songs were the size of bars, barns, and factory farms. This music scene in the form of a record label was booming out from the heartland, and it filled me with a sense of hometown pride and possibility. My tears were part of a regional pool.

All of this was particularly exciting because I thought Oberst's songs, and especially his lyrics, were objectively good. Objectively great. Many of his turns of phrase still work on me today, but I can see now that they were really just very clean. (Unlike some of his rhymes, which could be dirty as sin. The man rhymes "orange" with "soil." That shit flies in Nebraska, though.)

He lays out perfect bummer couplets like a mason: "But me I'm not a gamble, you can count on me to split / The love I sell you in the evening by the morning won't exist." He rarely mixes metaphors, his short-story-type songs snap shut, and he's obsessed with parallel constructions, which formally reflect the ambivalence so many of his lyrics promote. Take this line, for example: "You can save face but you won't ever save your soul." Or this one: "To love and to be loved. Let's just hope that is enough." Or this one: "You write such pretty words, but life's no storybook." Or this one, from the most Midwestern wedding song ever: "I'd rather be working for a paycheck than waiting to win the lottery." As he says, "If you say that there's no truth, then who cares? How come you say it like you're right?"

What, you want me to defend every time he earnestly says the word "despair?" I won't. But a full 65 percent of these songs do hold up, and they participate in a workaday country/folk music tradition that will get a ho-hum Midwesterner like me through the week.

And then there are the love songs.

Especially in the earlier years, Oberst wrote a lot of songs—"The Calendar Hung Itself," "The Center of the World," "Sunrise Sunset"—from the perspective of a creepy, obsessive romantic who would threaten to commit suicide and/or drink himself to death if you didn't love him back.

The high-school boys who identified with those songs probably made shitty, fake-out feminist boyfriends. I may have been one of them on occasion. I'm sure I learned to be that kind of asshole, in part, from these songs.

But Oberst's best love songs—like all good love songs—combined the personal, the political, and the extremely particular. He became the master of the "Girl, You Ain't Lookin' So Good (But Neither Am I)" song, e.g. "Four Winds," "Lua," "Land Locked Blues," "Laura Laurent," "We Are Nowhere and It's Now," "Gossamer Thin." This genre reaches its apotheosis in his (forgive me) Brooklyn-noir masterpiece, "Lover I Don't Have to Love," which—fuck me for still loving it. I never had a druggy girlfriend who believes that love's an excuse to hurt and be hurt, but I never stopped looking.

Speaking of Brooklyn, the speakers in Oberst’s songs always seemed to be three to five years ahead of every hipster cultural trend, which put him about 10 years ahead of me. They were indulging in Brooklyn cocaine binges in 2002, a full three years before the national papers started noticing Williamsburg. They went out to the spiritual woo-woo West with Cassadaga years before LA started becoming acceptable again. And they fully embraced socialism in The People’s Key (2011) five years before Bernie gave us a future to believe in (or at least a future future). Depending on where you live culturally, Bright Eyes was the harbinger either of hope or of ruin.

If that's the case, the fine people of Asheville, North Carolina, better start buying single-family homes now. On the cover of Ruminations, Oberst sits straight-backed on a bench in front of an upright piano. He's got a new old blue suit, a bedhead cut, and a hands-free harmonica. Despite the artist's many comings and goings, on this album, everyone's still looking rough. God's still dead, but love's still conquering all (fingers crossed). "Primitive" rhymes with "John Muir did."

And as for you idiot liberal kids recently escaped from the flyover diaspora: "Be careful with your headphones on when you cross the FDR / Don't wanna be a casualty before you make it to the bar. / Hide your shakes and worried face, just sit down in the back. / Your friends got there ahead of you." The only difference is, on this new album, he seems distant from those friends, as if he still has the music but—owing to perfectly understandable circumstances from his private life—he's lost the company.

For those who have defected, for those who have deserted him over the decade and a half of his time making music, he's got a special Shakespearean message for you in "You All Loved Him Once," one that hit me hard in the final hour of my Bright Eyes marathon:

You all loved him once

Yes you ate out of his hand

He mirrored your confusion

So that you might understand

Then your soul was an experiment

So he drew a diagram

You all loved him once

It ended bad

But it didn't end bad. I'm as surprised and pleased as anyone to report that, in fact, it didn't end at all.