In Light Of ‘Ruminations,’ Here’s A Very Deep Dive Into Conor Oberst’s Career

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“Some things go south and they never turn around,” Conor Oberst sighs, in his distinctive Omaha whine, toward the end of Ruminations, his remarkable new LP. It’s a sentiment that squares with the rest of the album, which is at turns bitter, insightful, angry, sorrowful, funny, and self-pitying. Written after a period marked by health problems and a potentially career-ending controversy, Ruminations mostly ruminates on Oberst’s pet concerns — emotional and mental illness, and the collective psychosis that enables celebrity of the political, religious, and show-business persuasions. Musically, Ruminations is the most stripped-down album Oberst has made since his teens, centering on Oberst’s voice, guitar, occasional piano, and wheezing, Dylanesque harmonica. Recorded in around 48 hours, many of the songs sound like they were written shortly before they were laid down, before Oberst had time to revise or reconsider their implications.

These trappings suggest a redux of Bruce Springsteen’s Nebraska actually recorded in Nebraska. But Oberst is less concerned with the death of the American dream than bearing witness to the last glimmers of an accomplished, drawn-out youth. On Ruminations, Oberst is his own Charlie Starkweather, seeking to murder pain and provoke catharsis amid the barren landscape of his personal headspace. Which is to say, he’s finally all grown up.

I’ve been playing Ruminations a lot in the past few weeks, along with The Studio Albums 2000-2011, a box set collecting six LPs that Oberst recorded with his most popular band, Bright Eyes, as his indie fame surged, crested, and then receded. Ruminations aligns with those records in unsurprising ways — from his early 20s to his mid-30s, Oberst has remained an incurable sad-sack who co-mingles the personal and the political more effectively than any singer-songwriter of his generation. Ruminations feels like a culmination of those earlier records, which sometimes purposely, more often not — charts Oberst’s uneasy odyssey not just from boy to man, but from underground hero to indie superstar to an uncertain place between those poles.

In the prime of Bright Eyes, Oberst was a defining indie-rocker of the ’00s, singing NPR-friendly anthems of romantic longing and spiritual questing that resonated with 20-somethings searching for meaning in the shadow of 9/11 and the Iraq War. Oberst seemed to embrace the mantle of generational figurehead, touring with Bruce Springsteen and lambasting George W. Bush on The Tonight Show. His records were emblematic of their time, but then that time passed. Now, it’s been almost a decade since Oberst resonated as a significant pop-cultural figure.

More recently, the 36-year-old Oberst was tarred with a rape accusation that was later rescinded, and diagnosed with a brain cyst that, for now, appears to be benign. According to a recent New York magazine profile, Oberst has been spending more time back in Omaha lately, echoing the “reboot” vibe of his new record. The question with Ruminations is whether the rise-and-fall narrative that unfolds on The Studio Albums: 2000-2011 now has a redemptive epilogue.

Born and raised in Omaha, Oberst was a rock prodigy, recording his first album, Water, at the ripe old age of 13. The following year, Oberst formed an emo band, Commander Venus, while on the side recording solo tracks under the name Bright Eyes. Those songs were finally released in 1998 after Commander Venus broke up, swiftly followed by a proper album, Letting Off The Happiness.

Oberst’s feelings about these early recordings — as anyone who winces at their own high school yearbooks will understand — appear to be noncommittal. For the box set, the Bright Eyes story officially commences with 2000’s Fevers and Mirrors, a fevered, sweeping alt-rock pastiche that left an indelible impression still implanted on Oberst’s music. Again, the specter of youthful indiscretion lingers — imagine someone dictating and then publishing your inner monologue from an average day when you were 20, and you have a decent approximation of Fevers and Mirrors. “The Calendar Hung Itself,” a pitch-perfect replication of an epic undergraduate romantic meltdown, is indicative of the album’s near-hysterical emotional volume.

A few years later, in an interview with The A.V. Club, Oberst was already distancing himself from Fevers and Mirrors, preferring that his critical breakthrough, 2002’s Lifted, Or The Story Is The Soil, Keep Your Ear To The Ground, be regarded as the first Bright Eyes album.

“I mean, I wrote [those songs] when I was that age,” Oberst told Spin in 2014. “For whatever reason, some of my old records are totally a high-school thing: You come to high school and someone hands you one. I know that to be true because I get the royalty statements. Someone’s still buying those records and I assume they’re not 40 year-olds. It’s like that first Violent Femmes record, Catcher in the Rye: Something that’s so easily understood at that stage in life.”

Just as Bob Dylan for some will forever be cast in amber as a finger-pointing activist folkie, Oberst has long been fixed as the aggressively verbose post-adolescent manic-depressive of Fevers and Mirrors and Lifted. This is at least partly due to the lasting power of those records, which remain overwhelming in their ambition and verve, as well as the polarizing quality of Oberst’s tortured yelp. Oberst’s talent, then and now, is undeniable, but his determination on his early records to Blow You The Eff Away with every anguished turn of phrase, cataclysmic orchestral flourish, and overwrought vocal turn was bound to win disciples and haters in more or less equal numbers.

In retrospect, Oberst’s persona at that time resembles the cultural shorthand now commonly associated with millienials. He was earnest. He was precocious. He told you how much he cared. He had strident opinions about an adult world that he wasn’t experienced enough to truly understand. He seemed to try way too hard. For the media, Oberst signaled a change of the guard. Jeff Mangum, who ran from stardom and essentially retired just as Neutral Milk Hotel seemed to be approaching critical mass, was a quintessential Gen-Xer, a quirky outsider distrustful of mainstream success. Oberst, meanwhile, pointed to the rise of a proactive, upwardly mobile can-do-ism that would calcify into a generational caricature by the end of the decade.

Oberst himself became a kind of caricature almost immediately — a “cartoon of an indie rocker,” to quote a New York Times Magazine profile from 2002. As much as his songs, Oberst’s fragile, cherubic good looks were fetishized and later utilized by Jonathan Franzen and a million hacky music critics as a signifier of naive indie-boy sensitivity.

“His hair flops around his head in a black bubble, and above the quickly drawn lines of his mouth and nose his soulful eyes stare out,” the Times gushed. “Though he’s from Nebraska, he brings to mind some Japanese pop icon — Hello Kitty perhaps — the way he manages to seem both adorable and haunted at the same time.”

Given the hilarious fake radio interview at the end of Fevers and Mirrors‘s “An Attempt to Tip the Scales,” Oberst seems to have anticipated this misplaced deification. (Or he might’ve just been a Scharpling & Wurster fan.) Nevertheless, for a time, Oberst leaned into his it-boy image. Bright Eyes’ involvement in 2004’s Vote For Change tour featuring Bruce Springsteen and R.E.M. officially placed Oberst in the continuum of Important White Male Rockers, and he followed this exposure with his most immediate and popular album, 2005’s I’m Wide Awake, It’s Morning.

My theory regarding the contemporaneous Digital Ash in a Digital Urn is that Oberst was giving himself an “experimental” cover for the pop calculations of I’m Wide Awake. Simplifying and sentimentalizing his songwriting, Oberst filled I’m Wide Awake with scores of slam-dunk tearjerkers and surefire wedding tunes. Whereas the coldly electronic Digital Ash runs on great ’80s mixtapes and bad drugs — it was designed to be the “underrated” record — I’m Wide Awake is all warmth and charm and proto-Lumineers twinkle.

If that sounds like faint praise, it’s not meant to be. The songs you might remember soundtracking your first sh*tty post-collegiate apartment (“First Day Of My Life,” “Lua,” “Land Locked Blues”) hold up just fine, which speaks to Oberst’s blossoming melodic gifts. I’m Wide Awake stands as Oberst’s most successful attempt to make an album that can exist outside of whatever personal melodrama Bright Eyes fans projected on to his songs. Unlike the earlier records, I’m Wide Awake wasn’t a matter of life and death. It was “just” a collection of very well-constructed tunes that someone with zero investment in Bright Eyes’ previous albums could appreciate.

That said, I’ve always personally preferred that album’s stranger and more perverse sequel, 2007’s country-rock fantasia Cassadaga. A windy travelogue centered on a real-life community of psychics and mediums in Florida, Cassadaga is Oberst’s John Wesley Harding — a series of deeply coded, spiritually minded songs that double as troubled meditations on stardom.

While Oberst was a never an actual pop star, the intensity of his following had reached a fever pitch after I’m Wide Awake and Digital Ash. He would come to experience the bad side of fame without the benefit of the best perks. Remnants of Conormania linger to this day — in that New York story, there’s an anecdote straight out of an indie-rock version of The King of Comedy, in which a disgruntled fan asks for a selfie, gets turned down by Oberst, and then cold-cocks him. For all his detractors, it’s no wonder that Oberst has long seemed more ill-at-ease among those who love him beyond all reason.

When I saw Oberst perform on the first date of the Cassadaga tour in Milwaukee, the mix of extreme hero worship and extreme drunkenness in the audience was disorienting, like hanging out with Branch Davidians at an irresponsibly inexpensive happy hour. Young women screamed “Have my baby, Conor!” before passing out. When Oberst and his 11-piece band appeared, they were dressed in all-white suits, underlining the cultish atmosphere in the room. But Oberst didn’t comport himself like a messiah — instead, he exuded profound discomfort. Oberst wound up cutting the encore short after charging like a bull into his own string section, prompting the tour manager to literally pick him up and carry him off-stage.

Afterward I thought about “If the Brakeman Turns My Way,” a stately piano dirge in which Oberst wishes for “a place to level out.” The song’s central metaphor romanticizes a life guided not by overpowering artistic ambition, but rather fate. “I never thought of running / My feet just led the way,” Oberst sings, sound less like a typical 27-year-old dude than an old-before-his-time rock lifer burned out from playing in bands constantly for almost 15 years. Another variation on this theme kicked off 2008’s Conor Oberst, released after Oberst put Bright Eyes on hiatus. In “Cape Canaveral,” one of his very best songs, Oberst cops to being an adrift former child star, first likening himself to a rocket shooting across the sky, and then putting himself on that rocket blasting off from the rest of civilization.

“I know that victory is sweet even deep in the cheap seats,” Oberst argues at the close of “Cape Canaveral,” and after that, he basically did check out for a while. (On the LP cover for Conor Oberst, he’s sleeping in a hammock.) Conor Oberst initiated his “polished professional” era, which also includes 2009’s Outer South and 2014’s Upside Down Mountain. At this point, craft supplanted inspiration; though not without their charms, these albums are as slight as his early work is dynamic. With 2011’s The People’s Key, Oberst made the first and only impersonal Bright Eyes record. Instead of aping the Smiths, Oberst had taken to emulating Interpol, pumping up the ear-candy quotient and submerging the lyrics amid Texas indie musician Denny Brewer’s nonsensical braying about the etymology of “pomegranate.”

Oberst seemed to sense that he was flailing. “I’m like a person who wants to be a chameleon, but is a bad one,” he confessed to Spin in 2014. Nevertheless, Oberst insisted that “My goal is never to convey details of my own life for its own sake. If I wanted that I would write a memoir or go to confession.” Oberst said this as his personal life was imploding in the aftermath of a female fan accusing him of rape on an xoJane message board in 2013.

Oberst sued for libel, and the accuser recanted, but the incident short-circuited the publicity campaign for Upside Down Mountain, and threatened to permanently put Oberst out of commission as a major artist. When Oberst tried to retrench by reuniting the politically minded punk group Desaparecidos, whose 2014 LP Payola was far more spirited than Oberst’s comparably staid solo work, the support tour fell apart after Oberst fell ill.

In a sense, Ruminations is Oberst’s ultimate retreat — he sings alone, he plays alone, and he writes about being alone. No matter his protestations to the contrary, Ruminations can perhaps only be interpreted as a confessional work. At times, Oberst seems to deliberate bait critics in that regard, like when he references his health issues and threatens to put a gun in his mouth in “Counting Sheep,” or when he expresses ambivalence about meeting Lou Reed and Patti Smith in the stunning “Next of Kin.”

But that’s nothing compared to the bile of “You All Loved Him Once,” in which Oberst describes a fallen hero whose followers’ love “turned to hate.” In one of the most brutal stanzas, Oberst appears to address the people who turned on him, in the most vicious subtweet of one’s own fans since Dylan’s “Positively Fourth Street.”:

“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”

At the risk of trivializing Oberst’s personal ordeals, the shock to his system seems to have galvanized him. For the first time since Cassadaga, Oberst has made an album with real stakes. He’s even introduced a new element to his writing: Humor. Granted, the wit of Ruminations is so dry and misanthropic that it’s barely perceptible. Nevertheless, even the faintest hint of humor is a welcome respite. In “A Little Uncanny,” Oberst praises Jane Fonda for protesting the Vietnam War, calling her “a symbol for a pain she never knew,” which could also apply to Oberst’s relationship with his own fans. In the next stanza, he flips the celebrity activist narrative to the song’s villain, Ronald Reagan, who was “man enough” and “tan enough” to pull the country to the right. (Later in the same song, Oberst namechecks Christopher Hitchens, Oliver Sacks, Robin Williams, and Sylvia Plath — four dead people, two from cancer, two from suicide. Read into that what you will.)

Ruminations concludes with its best song, “Till St. Dymphna Kicks Us Out,” an ode to day-drinking that references one of Oberst’s favorite haunts in Manhattan’s East Village. After spinning so much oblivion in the previous nine songs, Oberst finds a grace note amid the destruction. Yes, sometimes things go south and stay that way. “But if you want a confidant,” Oberst adds, “I’d never let you down.” Not exactly a happy ending, but it’s a start.

Steven Hyden is Uproxx’s Cultural Critic and the author of Your Favorite Band is Killing Me and an upcoming book on the rise and fall of classic rock. Say hello to him on Twitter.