STORY OF THE SONG #6: ‘I Am Trying To Break Your Heart’

“I am trying to break your heart
I am trying to break your heart
But still I’d be lying if I said it wasn’t easy
I am trying to break your heart.”

The opening song on Wilco’s fourth album ‘Yankee Hotel Foxtrot’ is a big one. Not only is ‘I Am Trying To Break Your Heart’ a work of art, it’s also the title the band gave to the acclaimed documentary of the making of their fourth album by director, Sam Jones.


It was the beginning of the new Millennium and Wilco were about to cement their reputation as one of America’s greatest groups. The problem? The band’s record company had second thoughts. “The response we got from Reprise was they didn’t like it,” Jeff Tweedy told Rolling Stone. “The only specific direction I heard through the grapevine – I never had a direct dialogue with anybody – was that they said the vocals were ‘masked’… I couldn’t figure out what that meant.” Fans of Wilco fell for the dreamlike narration singer/songwriter Tweedy brought to Wilco’s best tunes, but on songs such as ‘Jesus, Etc.’, ‘Kamera’ and ‘War On War’ listeners were being challenged to lean in a touch closer than ever before. Then there was that opening song and its abstract intro…


See what we mean about a work of art? Picasso-esque in its wanton unshackling of convention, the song opens with white noise bleeding from the speakers until the warmth of gently-strummed acoustic guitars bring with them the promise of melody with a beat that’s relentless as rain. “What was I thinking?” sings Tweedy as the band try to figure out the answer to his question with cyclical piano figures, keyboard runs and stuttering Ringo-like drum fills. The recording fragments again around five minutes in and critics who’d proclaimed Wilco as ‘America’s answer to Radiohead’ get ready to tell us they told us so. “I was trying to find something else in there that was more exciting than six chords strung together with a bridge and a chorus,” revealed Tweedy. “Country songs on jukeboxes in bars always sound better to me than playing country records at home.”


Live versions of the song have developed over the years since ‘I Am Trying To Break Your Heart’ was released, but Wilco presented it pretty much as straight as could be from the start. A fan and festival favourite in the set-list, taken from the band’s biggest-selling album to date, the song’s lyrics take on different meanings whenever Tweedy, Wilco, the music industry or America itself lurches from happiness to heartbreak and back again. Lines such as “I am an American aquarium drinker”, “I want to hold you in the Bible-black predawn” and “I assassin down the avenue” have been catalysts for debate amongst fans since the song was committed to wax. But what does it all really mean? “If you can make up an arbitrary set of rules and follow them, inevitably things start to take shape and meaning,” Tweedy has said about the lyrics he writes. “Meaning exists whether you generate it or not and I think I’m more comfortable with identifying it than I am with generating something that I think is profound.”



JC Brooks & the Uptown Sound’s 2010 cover of ‘I Am Trying To Break Your Heart’ is one of Wilco’s favourite covers of their own songs. An incessant Motown beat and blaring horns highlight the high energy version and the song builds like a lost slice of classic soul. JC Brooks & the Uptown Sound are based in Chicago just like the 2022 Black Deer headliners and get inside ‘I Am Trying To Break Your Heart’, dance it to the end of love and bring it all back home again…


Read Story of the Song #5: You Are My Sunshine’ here.