The Top 20 Jeff Tweedy Songs: #3 “I Am Trying To Break Your Heart”

Videos by American Songwriter


“I Am Trying To Break Your Heart”
Band: Wilco
Album: Yankee Hotel Foxtrot (2002)
Key Lyric: “Let’s forget about the tongue-tied lightning/Let’s undress just like cross-eyed strangers/This is not a joke so please stop smiling/What was I thinking when I said it didn’t hurt.”

Time gets compressed and the city keeps blinking in this psychedelic, claustrophobic ode to an all-consuming relationship. “What was I thinking when I said hello” turns into “what was I thinking when I let you back in?” Tweedy admits his own culpability in the chorus: “I am trying to break your heart.”

The song kicks off Yankee Hotel Foxtrot,  Wilco’s watershed album, encapsulating the record’s mood and provides its musical mission statement.  A snatch of the later track “I’m the Man Who Loves You” can be heard during the song’s closing meltdown.

Employing his own internal poetry, Tweedy bends the English language to express all the intangibles of love and strife. “I am an American aquarium drinker,” goes the now iconic opening line. “I assassin down the avenue.” Some were confused by this; others were intoxicated.

Yankee Hotel Foxtrot reintroduced the world to an amazing and ever-evolving band, and helped turn Wilco into one of America’s most respected rock acts. The immediately arresting  “I Am Trying To Break Your Heart” was one of the primary reasons why they could no longer be ignored.


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  1. YHF is vastly overrated? I think you need to strap on a pair of headphones and put needle to vinyl once again my friend. On the other hand, YHF is not music for the masses, so maybe I’m just one of the lucky ones.

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