Cross-eyed Strangers

On Wilco, Yankee Hotel Foxtrot, and the lonely joy of being different

I wasn’t ready for Wilco the first time I heard them. It was 2004. After school, I went to my local audio + electronics store, A&B Sound, looking for something new to put in my stereo. On the wall behind the listening counter (remember those?) a 12” by 15” portrait-shaped grey poster of an egg looked at me and said, “Ask about me. I am interesting.” So I did.

The very cool woman unpackaging CDs in front of me tried desperately to hide her enthusiasm as she directed me toward the “W” section, adding that I needed to also hear the band’s earlier album: Yankee Hotel Foxtrot. I grabbed the “egg” album (A Ghost Is Born) and the one she mentioned with the cool buildings on it, handed them to her to insert into the player, and sat down, expecting to have my mind blown.

A Ghost Is Born didn’t land. The singer seemed out of key, like he wasn’t trying. The lyrics focused on themes I couldn’t relate to (domestic abuse, filling out tax returns), and the songs took forever to get off the ground. After a quick flip through the other tracks, I switched to Disc 2.

YHF felt like more of the same. Meandering. Repetitive. Noisy but not loud enough. It got a little groovier than AGIB, but I still didn’t like this Jeff Tweedy guy very much. My steady diet of The White Stripes, Matthew Good Band, and Rage Against the Machine at the time meant I was open to rough vocals, but maybe not in a way that could be perceived as lazy. I think I was looking for more passion.

Here’s the thing though: I couldn’t just stand up and leave. This older, much cooler girl was still standing there with her third-day-dirty hair, unpacking boxes. So I bought them. To avoid embarrassing myself and being thought by a stranger as a guy with less-than-stellar music taste, I bought them.

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It’s not every day that you find a reason to thank the horny, self-conscious, teenage version of yourself, but that’s how I feel right now. Within a year’s time, both albums were easily among my favourites. And this is when I began to recognize Wilco’s benevolent, isolating effect on my life.

During one post-church Sunday afternoon, I tried to hijack the six-disc player at my friend Rueben’s house and swap out the country and metal for Yankee Hotel Foxtrot. It didn’t go over so well. Instead of converting my friends to my new religon, I got an annoyed and/or disgusted “What is this?” I don’t think we even got all the way through “I Am Trying to Break Your Heart” before Rueben switched it back and the room full of peers breathed a collective sigh of relief.

I wasn’t completely alone in my love for Wilco. My younger brother Nick got on board pretty quick, and a group of his friends shared our fascination with this already-aging Chicago band. Nick and I picked up the back catalog, flirted with Tweedy’s former band Uncle Tupelo, and even added the solo albums and side projects of Wilco’s members to our CD collections.

Two years after I graduated, we formed a band with these friends and fellow Wilco-lovers, calling ourselves Alpha Beta Crayon.¹ Dan, Nick (the second Nick in the band), Tim, and (later) Dave introduced us to a long list of other artists that we both still consider our favourites: The Velvet Underground, Yo La Tengo, Animal Collective, and many, many more.

Why am I telling you all this? It’s not because of the 20th Annivesary boxset of Yankee Hotel Foxtrot that the band released last month, not exactly. It’s not because more people need to know about this album or the band that made it. Most people who will enjoy YHF have probably already heard it. I’m not writing a piece of free promotional material. Honestly, it’s more of a personal exercise. I’m trying to understand why this album has such a strong hold on me.

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I recently read Lindsay Zoladz’s New York Times article about YHF. In it, she discusses the documentary I Am Trying to Break Your Heart, a film that tells the story of the album’s creation, major-label rejection, and defiant success. The doc, released in 2002, helped turn the album into a symbol of hope for independent artists and music lovers in the early ‘00s.

But Zoldadz doesn’t focus too much on all that. Instead, she points to the heart of Trying to Break Your Heart—the difficulty and dissonance in the band’s inner dynamic, specifically between Tweedy and his then-writingmate, Jay Bennett. To Zoldadz (and most other critics) the doc presented Wilco as Jeff Tweedy’s band, casting Bennett as an overly opinionated second fiddle that wore out his welcome midway through the recording process. Zoldadz compares this “Jeff as hero, Jay as villain” narrative to the one weaved in another, newer doc, Where Are You, Jay Bennett?, which attempts to turn the tables and give Bennett the credit and legacy he deserves.

In the middle of all that, Zoldadz stuffs a stunning detail from the second film in brackets:

(“Perhaps the film’s greatest service is the details it fills in about Bennett’s 2009 death: Often reported simply as an overdose, Bennett died of a faulty fentanyl patch he had been given by doctors to mitigate his pain before hip surgery.”)

I identified with Jay Bennett when I watched I Am Trying to Break Your Heart in 2007, a feeling that grew stronger over time. While I’ve been on both sides of the Tweedy/Bennett dynamic—forced to have a difficult conversation with a bandmate as its leader, and being cut from another group’s lineup—I never saw myself as the alpha of any social group and often felt like I had to earn my place in the closeknit environment that is a band.

In 2009, Bennett’s death hit me hard, especially for someone that didn’t know him personally, and the insinuation that his “overdose” had anything to do with his removal from the Wilco lineup never sat well with me. At this point, with the revelation highlighted by Zoldadz adding some much-needed context, the whole Tweedy v. Bennett discussion mostly serves to illustrate one thing: you never get the whole story.

That said, I recognize that I empathized with Bennett for the same reason I grew to love Wilco’s music. Both the man and the band have an “outcast” quality to them. They’re different. They don’t run with the crowd. Their ideas don’t always mesh well with the group. And they seem to understand the suffering that comes with that.

Take the lyrics found on YHF. These ain’t your silly love songs. Much discussion surrounding them has focused on Tweedy’s writing process at the time: finding words and phrases in other writing (newspapers, magazines, etc.) and sticking them together to make a kind of collage. But combined with his “squeeky, unsure” voice (as he puts it), the seemingly disjointed lines always find a way to hint at the specific and profound.

Track by track, the same themes pop up: disconnection from loved ones (what was I thinking when I let go of you?), emotional crisis (phone my family; tell them I’m lost on the sidewalk, and no, it’s not okay), loss of innocense, both personally (playing KISS covers, beautiful and stoned) and nationally (I would like to salute the ashes of American flags and all the fallen leaves filling up shopping bags). They all end up pointing to a relatable yet isolating internal struggle: the impossible walls between your inner self, yourself, and others: unpenetrable isolation.

These songs are sad. But the way Tweedy expresses the sadness in them—the odd turns of phrase paired with intimate details—makes them surprisingly relatable. And that relatability sends a shock of joy to the listener—at least it does to me.

The final track, “Reservations,” might be the strongest example:

how can I convince you it's me I don't like
not to be so indifferent to the look in your eyes
when I've always been distant 
and I've always told lies 
for love

I'm bound by these choices, so hard to 
make
I'm bound by the feeling so easy to fake
none of this is real 
enough to take me
from you

I've got reservations
about 
so many things
but 
not about you 

I know this isn't what you were wanting me 
to say
how can I get closer and be further away
from the truth
that proves it's beautiful 
to lie

How does another human-being not connect with that brokenness? And yet, the song is about exactly that: how hard it is to be fully known and understood by others. The paradox shines a different kind of light on the dynamic between Tweedy and Bennett at the time, one less focused on justice and more on the sadness of disconnection and lost friendship. Listening to Yankee Hotel Foxtrot now, with all this in mind, makes me want to text all my old friends, from Rueben to Nick and everyone in-between, to say “Hello!,” “I’m still here,” and “I love you.” We’re not all the same, but in a way, that makes us all the same.

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What about you?

1. Is this album part of your personal canon, too?

2. What music makes you feel different from others?

3. Were you ready for Wilco when you first heard them? Are you ready for Wilco now?

4. What album makes you want to hug your friends?

Leave a comment. I want to know!

1. Despite its suggested ties to YHF, the band name was actually given to us by another influence, Blitzen Trapper, while fanboying with them after a show at the University of Washington.