Wilco's Jeff Tweedy on the Meaning Behind His Song "I Am Trying to Break Your Heart"

Jeff Tweedy, frontman of the band Wilco, talks about the meaning and language of his song "I Am Trying to Break Your Heart" and the emotions of live performance.
Tweedy appeared at The Connecticut Forum "Creative Minds" on December 9, 2021 along with actor Nick Offerman, poet Tracy K. Smith, and moderator Alison Stewart.

[@angellacanfora]

He's an American treasure, will go down in history as one of the all-time great songwriters. So very grateful to have become his fan early on - 1995 - and to have had his music as the soundtrack to my life!

[@joygimbel7760]

He already is

[@deglispiriti]

I jumped on the train in 1998. How amazing to see all those great songs live, when they were WIPs. Thank you, Jeff, for also being the soundtrack to my soul.

[@stevemills1960]

No. He’s an American aquarium drinker.

[@louisjwilliamsii]

This song moved me when I first heard it. Years later it still speaks to me in completely different ways. I love songs that can evolve with you. What I like about Wilco is most of their songs mean different things to me as I get older. It's like listening to them for the first time every few years

[@j3nji]

Well you fking succeeded Jeff Tweedy. I tear up every time I hear your music. In fact, when I saw you live in Portland, Maine many years ago I cried through the entire show like an absolute psycho. When I was introduced to your music many many years before the Portland show it was during a time when I was falling in love. I leaned on your music through all the ups and downs of that relationship and then when we saw you at the State theatre it all just bubbled up and over. So /wave I was the nut bawling through your performance.

[@minaguta4147]

Love this. Thank you for sharing.

[@ApoorvBisht]

I've been listening to this song for about 10 years now, and finally recently every line means so makes so much sense to me in my own way..

[@christianholzel560]

The greatest!

[@blakewhittington4336]

I just want someone to love me enough that I could break their heart is my meaning for it

[@j.c7719]

I feel every line of that song deeply, it’s funny how lyrics are mostly just nonsense or stream of consciousness when you write them and then when you read or listen to them back, you realise it’s completely relevant to your life in that moment and expresses exactly what you can’t say.

[@joygimbel7760]

Best song name ever

[@duckman531]

To me, it's about trying to reunite with an estranged lover. It ain't easy, especially when this isn't the first time.

[@JDrevolver66]

The bits of (sometimes quasi) alliteration are another great aspect of the lyrics. Makes the images that much more vivid (the bible-black predawn, he *assassins* down the avenue.

[@bumfitmusic101]

Brilliant!

[@GreatEgret]

I believe JT said in the past that it’s about moving Wilco away from Alt Country into new styles of music. Summer Teeth was not well received by the Alt Country fan base when it first came out.

[@sonvolt9938]

Let's forget about the toe tied lightning.

[@eddiehopson5834]

tongue tied

[@imgitai]

Impressionistic

[@samwardlaw4239]

With a pinch of surreal

[@JeffWhite-cl2be]

Springsteen, melloncamp, and even many other artists with real talent and appeal can't hold a candle to the prolific writing of Jeff Tweedy, I wonder what impossible Germany could be about?

[@RealAsaMitaka]

Why is he old

[@rupman27isback]

So basically we still know Absolutely nothing about the song 😄

[@deglispiriti]

The reader is the writer and vice versa. Do you assassin down the avenue?

[@SonicRave1]

I always thought it was about kicking Jay out of the band? 🤷🏼‍♂️

[@SeenACowSki]

But Jay is on the song.

[@JDrevolver66]

Because of the movie it will always be associated with that, but it happened after they finished the album. The stuff between Jeff and Jay seems to have started during recording and especially the mixing stage. Jeff would have written the song before the sessions started (heck, along with the 8 tracks he and Jay co-wrote for the album).

[@philipbell9301]

Good one

[@deglispiriti]

@@JDrevolver66 Thanks for the insight. Yes, Jay is so integral to this record.