Jordan Beckett (Bootstraps) Talks Conor Oberst’s Upside Down Mountain

One of my best friends has a motto: In life, he who gives the least fucks wins. Which is basically saying, a successful person cares very little.

One of my best friends has a motto: In life, he who gives the least fucks wins.  Which is basically saying, a successful person cares very little.  He or she wins in life because they just don’t give a fuck about anything, ever.  But if this is my best friend’s mantra, his standard of success, then he is aggressively losing in life.  And, for that matter, so is Conor Oberst.

My friend is neurotic, obsessive and every life issue or even trivial nuance becomes a crushing level-10 concern.  For him, it runs the gamut from existential to personal aesthetic dilemmas — nothing is minor, everything is paramount.  Take, for example, drinking a 20-ounce coffee.  In his mind, drinking a Starbucks venti-size coffee in public projects to women that:

He’s an out-of-work stoner.
He’s a ‘gamer addicted to Call of Duty.
He has no social skills and is probably a virgin.
His diet consists of Tombstone frozen pizzas and vodka Red Bulls.
Due to this diet women assume he has grossly enlarged male breasts.

This is not hyperbole.  Those are highlights taken from a real conversation after I ordered him a 20-ounce coffee by mistake.  Walking down the street with a venti coffee was a deeply distressing proposition — these things torment his brain hourly.  But it’s a 20-ounce coffee, who gives a fuck!  But that’s the point:  He does.

But he saves even greater levels of insanity for life’s main concerns.  He devotes crippling care and focus to career, family, dating, religion, America, money, ethics et al.  He is constantly taking a self-induced mental beating.  It happens with such frequency and attack that he depends on that which takes your cares away.

Alcohol is always a reliable solution.

Years ago, after a night of drinking, my obsessive friend and I took a spontaneous road trip to San Francisco.  It was here that I discovered Conor Oberst’s music.  We were ostensibly driving from L.A. to visit his sister’s new baby.  But I had other motives.

It’s sickeningly cliché but I’d been hung up on a girl who seemed to haunt every relationship — no one could fill her shoes.  We hadn’t spoken in years but I thought about her daily.  I felt like, at best, I could only hope to find an acceptable replacement, an understudy.  As I drove that day, my friend slept off his hangover and I listened to the entire Bright Eyes catalogue on repeat.  I’d heard she lived in San Francisco now, and I debated looking her up when I got into town.  The whole idea was absurd, given the obstacles, but I couldn’t stop thinking about her.

It’s a weird relationship you feel with an artist who makes records, the kinda albums that play as a whole, each song builds into the next and so on until you feel fully submerged.  They’ve been reading your mail.  These are the kind of albums that Conor Oberst makes.  He lets you identify with his world and vice versa.  My obsessive friend and I were driving pissed off and so was Conor only he was crystallizing it line by line.  We had regrets and so did he.  And we were all disillusioned, which is what happens when you care too much and life seems to repeatedly tell you it doesn’t give a fuck.

On his latest, Upside Down Mountain, themes stay consistent.  And I love Conor’s single-mindedness.  Music is an art form, but it’s also a service industry.  As in, if you make whiskey, then distill the best whiskey — don’t diversify and also offer a white wine spritzer.  The record’s bio states that “loneliness, dislocation, and regret repeatedly surface” on the new album.  Sounds familiar, but on Upside Down Mountain the whiskey has aged and burns like hell.

When we got to San Francisco I looked up my distant ex on Google.  This was a longshot.  I found three different phone numbers that matched her name — I called all three and left three messages.  They were probably massively pathetic, extremely desperate-sounding voicemails.  I couldn’t care less.

Three hours later I got a call from an unknown number.  It was her!  We were both in the Presidio.  In fact, she was four blocks away.  We made a plan to get dinner that night at 8:00.

As I walked to meet her, I chain-smoked a half pack of Parliament Lights, panicked and mentally spinning out.  Oh shit, she didn’t even know I was a smoker now!  Even if she were single, my bad habit would probably be a deal breaker!  Did I have ashy, alligator smoker skin now???  Well, maybe if this worked out, I’d find a surge of militant self-motivation to finally quit smoking.  I mean, that’d be great, we could wake up early together and take spinning classes and then make raw kale-and-spinach smoothies.  I needed another cigarette and a venti coffee!!  No, I’m absolutely not showing up drinking a fucking venti!!!  I bought Listerine and Nicorette gum.

Our date that night was incredible.  It was honestly straight out of the movies, like that magical night in Titanic that’s capped off by Jack producing a charcoal sketch of Rose nude on a couch.  That’s a bold move and a memorable date idea if you can swing it.  I wish my night had ended with an impromptu naked portrait or a ride on the bow of the world’s largest sea vessel but strangely, it felt even better.  I walked home feeling like my existence was in perfect symmetry, not aimless and disconnected.

The ship sank a few months later, but after seeing her that weekend I finally gave in: If he who gives the least fucks wins, then I forfeit, I give up.  I could accept the loss, because on that long drive back to L.A. I couldn’t help but feel like I had won.

Jordan Beckett is a member of Bootstraps.  You can follow Bootstraps on Twitter here.