Wilco - I Am Trying To Break Your Heart

Although I’ve heard it described as Wilco’s “epic” before – its seven minute running time may commend this distinction – I’ve always felt that this track lacks a certain confidence that would warrant such a title. “I Am Trying To Break Your Heart” is the intense, honest and intimate story of one man’s experience with heartbreak. It doesn’t provide a universally relatable message or a transcendental musical experience. Instead, frontman Jeff Tweedy explores the dark underbelly of an essential human experience that is far too often chalked up to just roses and romance. This may be a song about love, but it is decidedly not a love song.

The story is built around a noisy backdrop that is as fragile as the protagonist whom it is supporting. Gentle layers of organ and guitar hide behind a piano part that plinks its way throughout the song, sometimes shy and others bright. The instrumentation grows more amelodic with each verse, matching the lyrical progression. Glenn Kotche’s drumming is artful, restrained and powerful. Meanwhile, Tweedy paints a poignant portrait of a man pushed to his limits by desire, turning in some of the most emotionally potent lyrics of his career:

“I’d always thought that if I held you tightly / You’d always love me like you did back then / Then I fell asleep and the city kept blinking / What was I thinking when I let you back in? / I am trying to break your heart”

Just as he sings the aching titular refrain, surrounded by dissonant, scraping guitar, a gorgeous and full-bodied chord pulls the song out of its own sadness and drives it towards a more melodic place. This, however, is just a temporary respite; soon enough the band dives back into dissonance, spinning a tasteful and sharp web of sound around distantly shouted lyrics. Pushed to his breaking point by the necessity of intimacy, Tweedy eventually collapses in a mess of noise and feeling. “I’m the man who loves you” he sings, his voice tinged with hints of desperation and loneliness.

I’ve always been fascinated by this song’s opening status on Yankee Hotel Foxtrot. Originally, I had thought that it would be the perfect way to close an album: a falling apart of sorts, slow and painful.  However, I have since realised that there is also something admirable to be found in its current placement. The song is about an ending, but it is also a beginning. On its own, “I Am Trying To Break Your Heart” is a tragic and shocking rumination on the destructive powers of love. At the top of an album, however, it is a welcome reminder that every ending, no matter how disastrous, will always be followed by something new.

— Brennan McCracken