On this date in 2002, Sam Jones’ I AM TRYING TO BREAK YOUR HEART: A FILM ABOUT WILCO was released in theaters. It came on the heels of the release of Wilco’s fourth studio album, Yankee Hotel Foxtrot, which became a major story in the music business (and for fans) when the band was dropped from Reprise after turning in the album, multi-instrumentalist Jay Bennett was unceremoniously dropped from the band, and Wilco found a new home with Nonesuch Records. Much of this activity was captured by Jones’ 16mm black and white camera in over 86 hours of footage, and then edited down to a mostly crisp 96 minutes that gave insights into Wilco’s creative process, and personal interaction, as well as presenting a bunch of killer live performances. Since I saw it in the summer of ’02 at the Varsity Theater in downtown Chapel Hill, it’s been one of my all-time favorite rock docs ever.


As this was back in the day with a much sparer internet, news of what your favorite band was up to could come rather slowly, but word was out in mid 2001 that Wilco’s much anticipated album, which had been set for a September 11 release (that’s right) was rejected by their label, and that both Bennett, and drummer Ken Coomer were now out of the band, so fans like me were clamoring to hear the record at the heart of this turmoil. Before Wilco themselves started streaming it for free, I found it somewhere online (can’t remember where) and it immediately became an all-time favorite record. It and Bob Dylan’s Love & Theft (which actually was released on 9/11/01) were my go-to albums for a long ass time, and still hit my turntable regularly.


The news that a film was being made about the sessions and album release aftermath was also in the mix as Jones was streaming unedited footage on his site (which is long gone) throughout late 2001-mid 2002. Yankee Hotel Foxtrot was finally released on April 23, 2002, an anniversary which celebrated around that date by Wilco with shows in New York and Chicago, and will be further commemorated with several different box set collections being released in September, but since the film itself hasn’t gotten much notice lately, I thought a timely look back was in order.

From the press kit for I AM TRYING TO BREAK YOUR HEART (2002)

I rewatched I AM TRYING TO BREAK YOUR HEART again last night for the first time in I don’t know how long, and found it to be a little more rough, and disjointed than I remembered, but still a solidly structured narrative about a band and an industry in flux. Many critics were on the money hailing its cutting depiction of art versus commerce as the film begins with the band deep into sessions for YHF, and feeling like Reprise has got their backs. 

After footage of Wilco front man, Jeff Tweedy, laying down a vocal track for “Poor Places,” and a lovely credit sequence featuring Chicago as shot through the rain-covered windows of an automobile in motion set to an acoustic demo of “I Am Trying to Break Your Heart,” we see the band rehearse and work on material at their Loft studio. The movie began shooting on the first day that drummer Glenn Kotche officially joined the band so that’s pretty damn notable.

We watch as Tweedy and Bennett talk up their situation with Bennett even saying, “I know it’s cool to bitch about your record label, but, I mean, they’re letting us make a record in our loft, and they haven’t heard a word of it. They’re giving us $85,000, and they haven’t heard a word of it.” As I wrote in Wilcopedia, “Like many of the multi-instrumentalist’s statements during the first half of the film, these words come back to bite Bennett’s ass in the second half.


But before we get to the central conflict, Jones gives us great, grainy footage of work-in-progress portions of the aforementioned “Poor Places,” “Ashes of American Flags,” and a fuzzy workout on “Kamera” (referred to as the “Troggs version in the DVD commentary.” There’s also some superb DONT LOOK BACK-esque excerpts (including “Via Chicago,” “Laminated Cat,” and “Sunken Treasure”) from a Tweedy solo show at the Great American Music Hall in San Francisco.


Now let’s dive into the stand-out scene in the – the argument between Tweedy and Bennett that foreshadowed the end of their relationship as collaborators and band members. This is an excerpt from my book of how it went down:

“Wilco reconvene at Chicago Recording Company Studios (aka CRC), where noted cellist Fred Lonberg-Holm is seen working out his part for ‘Reservations.’ There then follows a sequence of shots from the mixing board during work on ‘I’m The Man Who Loves You,’ which are used largely to set up the first event of friction in the film.


That would be the clash between Bennett and Tweedy, described in the commentary as the lowest moment in the making of the record, over the crucial edit between ‘Ashes of American Flags’ and ‘Heavy Metal Drummer.’Bennett keeps over-explaining his position about how to handle the mix while Tweedy tries and fails to be the peacemaker. It’s an incredibly awkward and painful scene that foreshadows Bennett’s dismissal from the band, and considering all that Bennett brought to Wilco during a key period in their career, it’s a shame that he’ll be largely remembered for this tense, awkward moment.

During a gig with his musical partner Edward Burch at the Local 506 in Chapel Hill, North Carolina, in 2002 not long after the release of the documentary, Bennett said from the stage, ‘I’m not an asshole, despite what you’ve seen at the movies.’ Meanwhile, while recording their commentary for the DVD, the other members of Wilco found the scene so hard to watch that they left the room while it played, leaving Jones to do his best to give some insight into what happened. They return after the worst of the scene has gone by—just in time for the bit where a migraine-suffering Tweedy goes into a restroom to throw up (filmed by Jones over the top of the stall).”

Following that, Wilco continues to hone the YHF material, with live performances at First Avenue in Minneapolis, and Bennett’s last live show with the band, which takes place at Petrillo Music Shell in Chicago on July 4, 2001. 

Jay Bennett waves goodbye after his last show with Wilco, Chicago 7/4/01.

The next thing we know, Bennett is out of the band, and Reprise has let them know that if they don’t change the album they should take it elsewhere. We witness Wilco’s manager Tony Margherita bitch on the phone about the situation, while rock critics Greg Kot, who wrote the first book about the band, 2003’s Wilco: Learning How to Die; and Rolling Stone’s David bitch about the sad state of the music biz in the early aughts.


The film’s musical climax is a blistering version of “Monday” from the aforementioned Fillmore concert. Interestingly, “Monday” was one of Bennett’s favorite songs to play live, and Tweedy and Company performed live it in tribute to him when he passed in 2009. The film then closes with the song that Wilco would often use to open their shows around this time, Anthony Newley and Leslie Bricusse’s ‘Pure Imagination,’ from the soundtrack to Willy Wonka & The Chocolate Factory, as we see the four members of Wilco—Bach, Kotche, Stirratt, and Tweedy—walking around a Chicago lakefront with the skyline behind them and their now brighter future in front of them.

In 2015, Tweedy discussed the doc at a special screening of one of his favorite films, Chris Smith’s AMERICAN MOVIE (1999) with the Modern School of Film’s Robert Milazzo at the Carolina Theater in Durham.


Tweedy: “I haven’t seen it in a long time, but there were a lot of moments watching that movie, well, there were a lot of moments during the filming of that movie where, uh, the first time there was an observing ego in the room – the camera…”

Milazzo: “Camera – you do such a beautiful song called ‘Kamera,’ which speaks to that…

Tweedy: “It just felt like, I don’t know if I’ve ever been able to put myself outside of myself enough to see what a camera might be seeing. And so there were a lot of moments during the process of making that record where I was like ‘oh, no – oh, no, that’s what the camera is seeing.’ Obviously, this is not – our relationship with Jay (Bennett) for example was made painfully obvious that there was a big problem in the way we were interacting, the way he was interacting with the band. And it’s really sad that it took a camera to do that or that we weren’t together enough, or grown up enough as people to see that without a camera.”


Sadly, I AM TRYING TO BREAK YOUR HEART isn’t as easily available as it should be these days. It’s not streaming on any of the majors – Netflix, Amazon, Hulu, Apple, etc. – and the DVD is out of print with used copies being pretty pricey, but it can be found, broken up into segments on Youtube. It was long available on Vimeo for rent and purchase, but has been recently removed.

The day before the anniversary of the retail release of YHF back in April, Wilco was photographed at the offices of Criterion, which may be a sign of an upcoming re-issue of the DVD (with hope a Blu ray edition) of the doc.


This would be fantastic for Criterion to add this film to their esteemed Collection. If you don’t know Criterion, they put out deluxe, often definitive editions of movies, and while the original had an extra disc of excellent material, fans know that there was a lot of stuff (the aforementioned 86 hours) Jones shot for the film (Jay Bennett said “We gave him three movies. It should’ve been a box set”), and this would be a great way for that stuff to see the light of day. 

I wrote to suggestions@criterion.com to request it, and hope my fellow fans will do the same. It ideally would help get it streaming again on their channel too.

So Happy 20th Anniversary to I AM TRYING TO BREAK YOUR HEART. Here’s hoping more folks, whether hardcore or casual Wilco fans, will give it a watch in tribute.

More later…

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