It was clear to Wilco’s Jeff Tweedy (
on Substack) , at least in late 2000, that the album they were expecting to release on Reprise records had three songs that would serve as the backbone to the record. ‘I Am Trying To Break Your Heart’ as the opener, ‘Ashes of American Flags’ in the middle and ‘Reservations’ as the end.Some things were less clear that year for the band. The role of drummer Ken Coomer had already been called into question, leading to Glenn Kotche replacing him. Inside twelve months, the tensions around the question of who would ultimately mix the album Jay Bennett or Jim O’Rourke would spill out on in the documentary movie I Am Trying To Break Your Heart: A film about Wilco alongside the issues with the record label that would ultimately see the band dropped.1
A reservation can be an expression of doubt, or it can be retaining something for future use. On ‘Reservations’, Tweedy insists that he doesn’t have the former about the object of the song, and the reality is the person he doesn’t like is himself. As the subject header here says, he does have reservations but not about you. Even twenty years on, I still remember the original Pitchfork review, a 10.0, saying there are no truer words to be said.
As a closer, the song performs two tasks; the first half gives us those final words and thoughts from Tweedy; it is a simple, literal love song that is mournful and still shimmers despite the near numbness of the vocal delivery as if delivered from the pits of depression. The second half of it is a slow, ambient drone, a break at the end of the album, a palette cleanse to allow us time to reflect and take in all of what has gone before. Ultimately, they would mine that well too much for my liking on 2004’s follow-up A Ghost Is Born, moving more in the direction of dirges on some tracks.
In recent years, the song has been played frequently around the middle of setlists. This from a 2009 show shows the song’s sheer power, even without the woozy interlude that concludes the album to reflect on the start of the track.
Another slightly different definition of reservation would be around keeping something back. On exiting their contract with Reprise, the band was asked to part with $50,000 to buy themselves out and repurchase the album. In the end, the label gave it to them for free.
Ultimately Yankee Hotel Foxtrot would go on to be Wilco’s best selling album. Buoyed by streaming from the band’s website, which saw an eightfold increase in traffic and gave their crowds at their late 2001 shows enough familiarity to sing along to technically unreleased songs. In 2002, to much critical acclaim, the album was eventually given a retail release on Nonesuch Records, who seemingly didn’t share Reprise’s reservations.
AOL’s merger with Time Warner that year and the latter’s shrinking share of the music industry lead to job cuts, including Reprise’s Howie Klein, a big supporter of the band. With no hits to that point and nothing on the record that felt like it would be, the label rejected it in June 2001.
Truly beautiful piece of music ✨ It's a new one for me and resonated with me deeply. Thanks for sharing.