Deciding just 15 songs out of Conor Oberst’s extensive 20 year back catalogue is no easy task. It requires careful planning, flow charts and a great deal of time to form. Following the release of his latest cohesive album Upside Down Mountain, the former Bright Eyes frontman still has grounds to prove that he’s one of the most relevant singer-songwriters in the digital age. Here are some choice cuts that may not be so obvious.

A full Spotify playlist is available to listen to and follow here.

The Calendar Hung Itself…

Starting proceedings as they mean to go on, ‘The Calendar Hung Itself…’ from 2000’s Fevers & Mirrors features Oberst detailing the plight of an over-possessive boyfriend (“Does he lay awake listening to your breath, worried that you smoke too many cigarettes?”). Oberst’s obsessive lyrics are a prominent feature on one of Bright Eye’s finest records.

The City Has Sex

In this choice cut from ‘Letting Off The Happiness’, Oberst uncorks his bottled up bitterness addressing loneliness and channels it into a powerfully short but sweet burst of aggression.

Mañana

It with Desaparecidos that Oberst showed how versatile he could be. Trading in his acoustic guitar for an electric, ‘Mañana’ perfectly demonstrates another side to the timid singer famously known for ‘First Day Of My Life’.

One of My Kind

A song which was criminally left on the cutting room floor following the Outer South sessions with the Mystic Valley Band, ‘One of My Kind’ details Oberst’s struggles with returning to his hometown following success, stating that he’s “Got so many broke friends who say I owe them from when we were children”.

Loose Leaves

A complete juxtaposition from most songs in Oberst’s arsenal, ‘Loose Leaves’ is a poppy new-wave effort which is sprightly and cheerful.

A Perfect Sonnet

Born out of envy and jealousy, ‘A Perfect Sonnet’ is a sharp, biting track that Oberst dedicates to romance. Lyrically, ‘A Perfect Sonnet’ is one of his most unrelenting and doesn’t hide behind any clever metaphors, directly stating “I believe that lovers should be tied together and thrown into the ocean in the worst of weather and left there to drown. Left there to drown in their innocence”.

Desert Island Questionnaire

A cut from Oberst’s latest effort Upside Down Mountain, where he encapsulates his fears into a 5-minute song which easily stands out amongst his extensive discography. The folks from First Aid Kit really decorate the tracks on Upside Down Mountain beautifully, but they really drive home Oberst’s pure angst when he sings “Everyone’s asleep in this burning building and I can’t wake them up in time”.

When The President Talks To God

In this song, Oberst details a theoretical conversation between George Bush and God. Known for his venomous tongue towards the Bush administration (especially on I’m Wide Awake, It’s Morning), Oberst pinpoints all of his aggression over a simplistic guitar rhythm. Truth be told, if there was a conversation between God and George Bush, we think it would go something like this.

Hot Knives

The fuzz-folk cut from the unapologetically orchestral Cassadaga features carefully arranged stabbing strings (no pun intended), grand excessive crescendos and the Dupree sisters from Eisley providing some luscious backing vocals. What’s not to love?

Get-Well-Cards

Oberst’s self titled album released in 2008 gained a lot of momentum and even managed to acquire the prestigious ‘Best Songwriter of the Year’ title from Rolling Stone (which he later acknowledged on ‘I Got A Reason #2’). ‘Get-Well-Cards’ takes the Dylan comparisons to another level.

Temazcal

Taken from the Monsters of Folk LP featuring M. Ward, Jim James and Mike Mogis, Oberst showcases his infatuation with Mesoamerican history with ‘Temazcal’, which features some of his most cryptic lyrics to date (“The love we made at gunpoint wasn’t love at all”; “The mayans stole tomorrow, hid it underground”).

Easy/Lucky/Free

Stating himself that this song is based on an optimistic outlook at death, Oberst’s philosophically apocalyptic lyrics paint a vividly dystopian picture (“I set my watch to the atomic clock, I hear the crowd count down until the bomb gets dropped”) over such a relaxed backdrop.

No Lies, Just Love

On the surface, ‘No Lies, Just Love’ is a simplistic four chord piano ballad. Dig a little deeper however, and you’ll find that it documents Oberst’s darkest hour where he seems as if he is about to burst into a stream of tears at any given moment during the song.

Road To Joy

A staple in Bright Eye’s catalogue, ‘Road To Joy’ closes out the perfect I’m Wide Awake, It’s Morning with an interpretation of Beethoven’s ‘Ode To Joy’. A performance on Late Night with Craig Ferguson perfectly displays how chaotic the climax of the song is.

Let’s Not Shit Ourselves (To Love And Be Loved)

In one of the most grand exits to an album, Oberst begins by screaming “Can I get a goddamn timpani roll?”. Clocking in at 10 minutes, the song features Oberst on top form lyrically and even manages to rival Bob Dylan at some points.

Honorary mentions:

Cartoon Blues
Endless Entertainment
I Got The Reason #2
It’s Cool We Can Still Be Friends
Jetsabel Removes The Undesirables
Te Amo Camila Vallejo