The 10 Best Conor Oberst Songs

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Conor Oberst has been writing songs since he was 13 years old. He’s 34 now, and in those two decades and change, he’s amassed a catalog that ranges from wounded folk songs with Bright Eyes to political punk anthems with Desaparecidos. He’s been the Americana troubadour, the muckraking activist, the lusty drunk guy stumbling around the Village and the man in love. There’s so much music from the prolific singer/songwriter that you get to see all of his sides, a near-complete portrait of the artist as a young and then slightly older man.

Much of Oberst’s strongest work so far fell between 2000 and 2005, bookended by the delightfully nervous wreck of Fevers And Mirrors and the double album I’m Wide Awake, It’s Morning/Digital Ash In A Digital Urn. The five-year period caught Oberst in the first half of his 20s, an age range primed for a kind of emoting that’s more articulate than a teenager’s but still too recklessly honest to pass as an adult’s. Oberst has released wonderful music since then, and some before, but it’s tough to top yourself when you’ve left that wilder person behind. In honor of Oberst’s latest album, Upside Down Mountain, released this week under his own name, here are the 10 Oberst songs you need to know.

10. “Mañana”
From Desaparecidos’ Read Music/Speak Spanish (2002)
Oberst got compared a lot to Bob Dylan when he started out, so consider Desaparecidos the equivalent to Dylan plugging in. The five-member punk band only made one album, with a title reflective of Oberst’s own self-improvement to-do list, and its songs offer social commentary directed at the group’s hometown of Omaha, Neb. On “Mañana,” Oberst nearly bursts a vein while screaming about rewriting the world’s future. This is what happens when emo folkies cut loose.

9. “If Winter Ends”
From Bright Eyes’ Letting Off The Happiness (1998)
The debut Bright Eyes album, a compilation of tracks Oberst wrote over two years as a teenager, was an unfiltered jumble. With the opening cut on his sophomore release, Letting Off The Happiness, Oberst steps up and shows an early glimpse of his potential as a songwriter (and of Mike Mogis’s talents as his producer). A clearer voice, a stronger melody and words about looking for an escape route give a more direct view into the mind of this restless kid in Omaha. He hasn’t smoothed out all of the edges, as he claws and cries his way toward the end, but he has funneled some of that fury into a song structure that gives shape to his fragility.

8. “Take It Easy (Love Nothing)”
From Digital Ash In A Digital Urn (2005)
Digital Ash In A Digital Urn is a good album, but it comes off looking like the ugly twin next to its release counterpart, I’m Wide Awake, It’s Morning. Though the latter album contains the higher quantity of better songs, Oberst did save a couple for Digital, one of which is “Take It Easy (Love Nothing).” An attempted friends-with-benefits situation goes awry, and Oberst is the recipient of a “this never happened” note. The brushoff turns him into a coldhearted villain, lying to get laid and kicking people out of his home once it’s over. And if any guests nag at his mind for too long, Oberst writes them into songs that he can shelve and forget.

7. “Method Acting”
From Bright Eyes’ Lifted Or The Story Is In The Soil, Keep Your Ear To The Ground (2002)
Lifted came out in August 2002, not yet a year after 9/11 and the start of the war on terror. Oberst was and is a vocal anti-war advocate, and though the song “Method Acting” never explicitly talks about the war, the topic is written throughout the music. The militaristic drumming, the unclear picture coming across his TV set and his request for someone to “Just tell us what to fear” all perfectly capture the mood of the time. Oberst even tells his players, “Boys, keep strumming those guitars,” in the tone of a captain encouraging his men to press on. It is Oberst’s attempt to figure out how his role as performer fits into the mess.

6. “A Perfect Sonnet”
From Bright Eyes’ Every Day And Every Night EP (1999)
Frustrated that you’re not in love? Oberst has an image for you: lovers chained together, thrown into a fire with their songs and letters and left to burn in their arrogance. It’s a touch on the extreme side, but sometimes you want your songwriters to go to the dark places so you don’t have to. Oberst drags his disgruntled feelings out from under the bed on this one and invites you to either join in or just watch as he heaves them around the room.

5. “The Calendar Hung Itself…”
From Bright Eyes’ Fevers And Mirrors (2000)
Oberst is a twitchy guy, and on this song, his nerves spread into his surroundings. The guitar isn’t strummed as much as it’s scratched like a bad rash, while Oberst bigs himself up as the more adoring lover compared to the one who may have taken his place. By the time he gets to repurposing some lines from “You Are My Sunshine,” his voice is ragged, his throat is raw, and there’s no way to believe that the person he’s singing about makes him happy when skies are gray, especially when he’s saying the words through clenched teeth.

4. “Cape Canaveral”
From Conor Oberst (2008)
Oberst released his first self-titled album in 2008, and perhaps in response to the rush of recognition that came from I’m Wide Awake, It’s Morning, the LP spends most of its time plotting an exit strategy. “Cape Canaveral” gently opens the album with a message of atonement woven within the strum of an acoustic guitar. A rocket’s path through the air and the open interstate offer two escape plans, and though they take different roads, they both satisfy Oberst’s need for a way out.

3. “Lua”
From Bright Eyes’ I’m Wide Awake, It’s Morning (2005)
Cold walks, cabs that won’t stop, rumors of a hip party you’ll never find, flasks on the subway: This is a New York night. As such, it’s going to strike a chord with anyone living in the area who’s gotten stranded after 4 a.m. on the Lower East Side in the middle of winter. But it will also speak to anyone whose simple late night conclusions look a lot more complicated in the daytime. Pigeons hanging on your window ledge might be a New York thing, but loneliness, addiction and destructive behaviors aren’t confined to city limits.

2. “Lover I Don’t Have To Love”
From Bright Eyes’ Lifted Or The Story Is In The Soil, Keep Your Ear To The Ground (2002)
Lifted blessed Oberst’s music with the gift of strings, and they’re put to good use on “Lover I Don’t Have To Love,” a song that’s about exactly what you think it is. Oberst shows his teeth on this one as he pursues a girl he just met and hunts for drugs after a show, while the strings and a wayward keyboard line build the drama. Poetry never dulls the narrative, leaving it so straightforward that there’s no way to misinterpret the song’s carnal, desperate nature.

1. “First Day Of My Life”
From Bright Eyes’ I’m Wide Awake, It’s Morning (2005)
There’s a reason you hear this song at all of your friends’ weddings, and it’s not just because the DJs refuse to play “I Just Called To Say I Love You.” In this lightbulb moment, Oberst realizes he’s found the person he loves and admits his happy feelings as openly as he usually proclaims his sad ones. Alongside the bright lines of an acoustic guitar, Oberst plugs up his bleeding heart and plays the optimist—a shocking and moving role change.

Check out the Spotify playlist here.