Wednesday, May 6, 2020

Wednesday Wilco Song Spotlight: “I Am Trying To Break Your Heart”


This series has been on hiatus since late last year, but it is starting back up today with the spotlight shining on one of Wilcos best known songs:

“I Am Trying To Break Your Heart”
(Jeff Tweedy)


The striking opening track of Wilcos fourth studio album, Yankee Hotel Foxtrot, has become a signature song for the band.

It earned such status by being a game-changer in terms of the perception of who the band are and were. It sounded like no other song they’d done before, yet it had the familiarity of Tweedy’s laid-back rasp for fans to latch onto.


Beginning with arguably the best opening couplet of any of Wilco’s albums, I am an American aquarium drinker / I assassin down the avenue,’ the song proceeds through punctuating walls of sound that seem to contain every instrument that exists, which isn’t so far-fetched as it sounds.

In a 2002 interview, former Wilco member Jay Bennett claimed to have played pump organ, Wurlitzer, two different pianos, a ‘noiz’ section (including toy piano), distorted synth, and manually re-amped drum effects on the track. It’s an everything-but-the-kitchen-sink production, for sure.


The arrangement of it evolved over a long time, Tweedy told Martin Bandyke in a radio interview. A lot of the pieces that kind of come and go, and the layers of noise, and just the chaos of it was an environment that evolved around the song more than something really mapped out initially. I think over time, the shapes started to emerge more.

Midway through production of Yankee Hotel Foxtrot, Jim O’Rourke was brought in to work with Wilco on the material, in particular this troublesome track. O’Rourke worked wonders on the song, weaving the sonic sections back together into a compelling albeit intermittently noisy narrative. 


Despite wanting to engineer and produce the album himself, Bennett admitted to Kot that the opener had been a freaky fucked-up song, and [O’Rourke] made sense out of it. (Fans can—and should—consult the Yankee Hotel Foxtrot Demos bootleg to get an idea of what the song originally sounded like.)

As the finished, O’Rourke-assisted song became the intro to the album, critics took major notice. Rolling Stone magazine’s senior editor, David Fricke, called it 
a minutely detailed portrait of the singer as blind drunk. Vibes, drums, piano, fuzz guitar and bicycle bells stumble over one another like they’ve been thrown out of a bar, and Tweedy slurs his metaphors in a heavy whiskey breath.

Pitchfork’s Brent S. Sirota chimed in by describing the 
slightly disconnected, piano-led track as being ‘delicately laced with noise, whistles and percussive clutter, like some great grandson of A Day In The Life.’

One thing that more than a few critics noted was that amid the cacophony-filled breakdown at the song’s end, Tweedy can be heard singing 
I’m The Man Who Loves You,  foreshadowing the song of the same name that follows later in the album. This doesn’t appear in the demo, or in any live version of the song.

When Wilco play the song live, it sometimes starts quietly, with a lone acoustic guitar figure; others times, it sounds like somebody has just powered up HAL 9000, as a electronic hum, ominous buzzing, and sci-fi-sounding synths fill the air.


More than a few live versions of I Am Trying To Break Your Heart are officially available: a stunning airing of the song recorded during Wilco’s May 2005 residency at the Vic Theatre in Chicago appears on Kicking Television, while another exemplary take on the song, filmed at the Mobile Civic Center in Mobile, Alabama, on March 3, 2008, was included among the bonus material on the 2009 DVD Wilco Live: Ashes Of American Flags

That same year, another Chicago band, J.C. Brooks & The Uptown Sound, released a cover of I Am Trying To Break Your Heart that reworks Tweedy’s abstract lyrics into pop soul come-ons.

When I sing “I Am Trying To Break Your Heart,” the unspoken line, I think, is if I could,’ Tweedy told D.I.W.’s Trevor Kelley in 2002. I can only break my own heart - I can’t break yours. I look at most songs as reminders of an idea or something that has helped me.

With nearly eight hundred live performances in the years since, I Am Trying To Break Your Heart is a helpful reminder of an idea that few of Wilco’s concerts are without.

An excerpt of a skeletal acoustic take of “I Am Trying To Break Your Heart” accompanies the credits at the beginning of Sam Jones’ 2002 documentary of the same name. Watch it below.



This is an edited excerpt from Wilcopedia by Daniel Cook Johnson, published by Jawbone Press (www.jawbonepress.com). Order your copy here.

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