[Editor's Note: Best Album Ever is a column where critics talk about their favorite records and what was happening in their lives when they got into them.]

I started at tony St. Louis liberal arts college Washington University in 1995, fresh from an upper-middle class St. Paul, Minnesota upbringing where I'd spun alt-country like The Jayhawks. But I had no idea this anachronistic, melancholy music would soundtrack my formative years — when I lost my virginity, found my calling, tried drugs, and otherwise engaged in growing up awkwardly.

My freshman year music dork conversations focused on local alt-country heroes Uncle Tupelo, who broke up in 1994. Everyone was forced to choose a splinter act — Wilco or Son Volt. I took Son Volt, of course, as Jeff Tweedy's new outfit sounded too much like the Replacements, and was too concerned with catchy tunes. As if those were bad things.

But though Still Feel Gone, Anodyne, Trace, A.M., and Being There are classic albums, none killed me like a band who came from outside St. Louis called The Bottle Rockets, particularly their album The Brooklyn Side. (The title references a bowling term.)

The music was nasty, in both the positive and negative senses: Over lumbering tempos and heavy guitars the group, fronted by former Uncle Tupelo member Brian Henneman, savaged Rush Limbaugh and called out high school assholes-turned-crabby-cops.

The tenor and lyrics of Henneman remind me of Texas native Steve Earle, not just in the twangy rock sound, but in the defensive, almost-shrill outrage against the evil empire.

I was down with outrage politics — totally fucking down, crafting a zine called The Nomad at my college, which before mocking the Greek system and the business school, published hackneyed investigative stories on the administration and lefty opinion pieces. (It took some chutzpah to critique the student government while also accepting funding from them.) Politics and art at the time went hand in hand for me, and a dream about changing the world through craft was partly why I loved the Bottle Rockets. There was no more powerful couplet to me than this one, from “Welfare Music:”

Quit school when she was 17

Senator on TV calls her welfare queen

Used to be daddy's little girl

Now she needs help in this mean old world

I used to get stoned and imagine a progressive future in which poor people could adequately support their families. I was inspired, even if, as the son of a doctor and an academic I hadn't experienced the American hardships I lamented. And my heroes mostly hadn't either; the bulk of the alt-country heroes came from middle-class backgrounds, worshiping at the altar of Bob Dylan, a regular kid from Minnesota who fancied himself a vagabond troubadour in the Woody Guthrie mold. I was a facsimile of a facsimile. This was all basically an excuse to indulge in self-pity, which can be fun, but gets old quickly.

So perhaps it's not surprising that, before long, I abandoned alt-country in favor of something that felt more real: hip-hop. While, again, I couldn't relate to the experiences described in rap songs, the messages seemed to come from a truer place. The genre felt closer to human struggle, and as a budding journalist I appreciated the street-level perspective. Further, with time I came to associate the themes of roots rock — yearning, solitude and heartbreak — with weakness, and no longer wanted anything to do with that 18 and 19-year-old kid so deeply affected by those emotions. The more I thought about it, I didn't want that pain (or the accompanying quixotic politics) in my life at all. I wanted to celebrate each day, to meet women and to exude confidence. Hip-hop was a perfect soundtrack.

But upon recently hearing that the Bottle Rockets were re-releasing both The Brooklyn Side and their self-titled 1993 debut on the occasion of the latter's 20th anniversary (out tomorrow, November 19, on Bloodshot Records), I put The Brooklyn Side back on. I tried to listen with a new perspective — without being embarrassed about who I once was, without self-hatred. What I heard this time wasn't alt-country pathos, but rather craftsmanship and inspiration that defy genre, with choruses and bridges that seem eternal. “Welfare Music” remains a Springsteen-caliber heartbreaker while “Thousand Dollar Car” and “I'll Be Coming Around” sound like radio songs that just so happened to not get much radio play. “Gravity Fails” has one of my favorite lines:

Calling you my better half

Is always good for a laugh

Don't get me wrong, the production is great — New York producer Eric Ambel gets much credit — but the songs' structures are so solid that with a little re-jiggering and a savvy programmer they could likely slide into just about any format in just about any era.

That group had only a short run on a major label and never broke big. This seems tragic, and the idea of Henneman still having to hustle hard through middle age makes my stomach churn. But, given the choice, it seems better to have crafted enduring art than to have briefly shone bright. Too often, the latter seems to be the goal in hip-hop, and in my own work as well. As a journalist and editor, I'm often tempted to set aside the enterprise pieces that take great effort in favor of blog posts that quickly go viral on the internet (and are just as quickly forgotten). Hard work is no guarantee of any payoff. It's got to be its own reward, and I suspect that for Henneman it is.

That's not to say wallowing in (or fetishizing) pain, which continues to be an alt-country trope, is a good idea, or that there isn't much to be said for hip-hop's good-time anthems. But it's clear to me now that the Bottle Rockets stirred many real emotions in me. Life is a painful thing after all — for everyone, poor or not — and their acknowledgement of that was cathartic for me. It is now, too. Sadness isn't an emotion monopolized by college students, and attempting to paper over it is no recipe for long-term happiness.

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