I believe that had Yankee Hotel Foxtrot come out as originally planned on Reprise, it would have been perceived as a failed experiment. Getting dropped by Reprise was the best thing that ever happened to Wilco. Instead of an indulgent, erratic attempt to merge classic rock and art rock, the band became a cause celebre and Yankee Hotel Foxtrot an indie touchstone, Pitchfork's emperor's new clothes.
I bring this up only because I believe it's time to re-evaluate "I Am Trying to Break Your Heart", which opens YHF as a sprawling mess but recently has been turned upside down into a soul stomp classic by Chicago RnB band, JC Brooks and the Uptown Sound. It's really quite a wonderful song, given the proper treatment. Check it out and see. - Teen Kicks
Streaming source: https://www.youtube.com/watch?v=zlxH9-TYseY