Song · Wilco
“I am Trying to Break Your Heart” by Wilco
From the album Yankee Hotel Foxtrot (2002)
“I am Trying to Break Your Heart” by Wilco appears on 13 radio countdowns from 7 stations between 2007 and 2025. It was first released in 2002 on the album Yankee Hotel Foxtrot. Its best result is #16 on The Best Opening Tracks of All Time. In the combined RockLists rankings it is #468 indie & aaa song of all time and #209 of the '00s.
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"I am Trying to Break Your Heart" comes from Wilco's Yankee Hotel Foxtrot, released in 2002. Jeff Tweedy wrote it alone and sings it like a man muttering through a fog, while the band, producing themselves, let the song lurch and clatter around him.
Jim O'Rourke mixed it, and the tune keeps surfacing and sinking under the noise, a pop song left out in the rain on purpose. It's disorienting, a little broken and weirdly tender, the kind of track that asks you to lean in rather than sing along.
Written with AI assistance from RockLists chart data, MusicBrainz.
RockLists rankings
Indie & Adult Alternative
All Rock Formats
All-time and decade countdowns
| Year | # | Station | Countdown | of |
|---|---|---|---|---|
| 2007 | 305 | WTMD | WTMD Top 897 Songs of All Time | 897 |
| 2009 | 110 | WYEP | WYEP 913 Songs That Matter from the Last Decade | 913 |
| 2013 | 106 | WXPN | WXPN 885 Greatest Songs of the New Millennium (2013) | 885 |
| 2014 | 195 | WXPN | WXPN 885 All-Time Greatest Songs (2014) | 885 |
| 2018 | 230 | The Current | The Current's 893 Essential Songs | 892 |
| 2019 | 64 | KEXP | KEXP Listeners' Favorite Songs of All Time | 627 |
| 2022 | 46 | 90.9 The Bridge | 90.9 The Bridge Top 909 Songs of the 2000s | 907 |
| 2022 | 260 | KEXP | KEXP Top Songs of the Last 50 Years (1972-2022) | 491 |
| 2023 | 325 | WYEP | WYEP Countdown to Fall 2023 | 1229 |
| 2024 | 34 | The Colorado Sound | The Colorado Sound Top 1055 Songs of the 21st Century | 1055 |
| 2024 | 85 | WXPN | WXPN The 885 Greatest Songs of the 21st Century (2024) | 885 |
| 2024 | 16 | KEXP | The Best Opening Tracks of All Time | 738 |
| 2025 | 574 | WYEP | WYEP Best Songs of the 21st Century (So Far) | 714 |
Also listed as: I Am Trying To Break Your Heart; I Am trying to Break Your Heart; I Am Trying to Break Your Heart.
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