The Making of "I Am Trying to Break Your Heart": A Film About Wilco by Sam Jones

Sam Jones's first real attempt at directing was the documentary "I Am Trying to Break Your Heart": A Film About Wilco which allows us to watch the band's creative process as they wrote and recorded "Yankee Hotel Foxtrot", the album that catapulted Wilco to the national level. Sam reminisces about those early days when filmmaking was a mystery which made it challenging and exciting.
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[@rac]

I had no idea it was the same Sam Jones. That wilco doc is incredible.

[@lajollascott]

Same here! TIL!

[@darrellgarrett72]

Yes it is!!

[@DazeyChaineMusic]

it’s mediocre at best. the narrative they painted of jay was really disrespectful

[@Nickpaflas]

Poor Jay Bennett. The rocked-up version of "Always in Love" in that movie is so great.

[@estudiosfolkloreiberoamericano]

Probably the highest part of the movie. It's so emotional and energetic!!!

[@MichaelHattem]

Unfortunately, Jay became the scapegoat in that film in a way that was quite unfair or at the very least depicted the relationships at the time in a way that was more fictive than reality.

[@casperguylkn]

The argument and Jeff puking are out of order for dramatic effect and that was unfair to Jay. Sam has never addressed any of it.

[@bif3578]

...and Sam Jones wouldn't agree to be interviewed for the recent Jay Bennett doc. Which is GREAT, BTW.

[@whitmore-project]

And kamera

[@Moondancin]

Yankee Hotel Foxtrot turned 20 years old. I was about 11 listening to this in my parents old Volvo. Time sure flies but this -took- always takes me back.

[@micheleazzu]

Sam Jones: - becomes a world class award winning photographer. - makes all by himself one of the best music docu in the history of the genre - creates and produces his own show that becomes very successful and unique in interpreting the process of the artist's life Also Sam Jones: most humble person in the world. HERO.

[@casperguylkn]

Sam Jones: hit job on Jay Bennett

[@jbyork]

That documentary was really important to me. I think anyone who is collaborating would benefit from watching it. I'm so greatful Sam made it.

[@kato64]

I had no idea he did the Wilco doc. Neat concept having someone interview the interviewer. Jason Sudekis was the perfect choice as guest host.

[@eltravos99]

I have come to love this show for a couple of years now and to learn that Sam did the Wilco doc...oh my god. That movie is so great! I love it. Sam, you are amazing!

[@loadiem31]

i had no idea he was the same sam jones!!!!!

[@LordOfDays]

I am also just realizing now that you directed that Documentary. Our senior year of high school we had a free class we do clubs in and we created "Music Club" which was more geeking out and "Listening to Music Club". Few of us could even play instruments. I vividly remember watching I Am Trying to Break Your Heart in club.

[@DK-qe6uo]

The music at the end of these videos makes me feel warm the same as finishing a level in Mario 3

[@jesseemullen]

I'm glad the new documentary on Jay came out. The I Am Trying To Break Your Heart documentary unfairly cast Bennett as the villain. Not cool

[@JohnSpo]

Jones stitched him up good. He's probably very much responsible for Jay's downfall.

[@_aworldthatspoke950]

@@JohnSpo lazy interpretation. bennet was was own victim, playing iago not just to Jeff but the other band members. maybe Jeff shouldn’t have fired him out right but the band were jaded from him trying to enforce input

[@JohnSpo]

@@_aworldthatspoke950 lazy interpretation? who TF are you? get fcked.

[@MarkAlanEffinger]

Is Sam Jones the Dick Cavett of New Media? He's found the ability to work seamlessly both behind and in front of the lens. Without muddying-up perspective. He's as much entrepreneur as photog, director, creative.

[@PhilEdwardsInc]

Found this after Google Stalking who this really good interviewer Sam Jones was - wow! Officially awesome.

[@chrisbredesen]

"You don't know the film you are making, until you get into the editing room." Best synopsis I've heard. I might steal that one. Sorry.

[@DOTTIE25]

My favorite documentary

[@LivLaRaj]

Vegas Sudeikis watched Opening Act Armisen a number of times before their big ensemble collabo at 30 Rock...

[@bradhart6487]

Like so many commenting here, I had NO IDEA that was the same Sam Jones! That film is brilliant...makes sense that he is so good in these interviews.

[@tfustudios]

Great doc! But recently learned the about the 'Jeff/ Jay argument- bathroom' scene.

[@marty88ish]

I think I have crushes on both of them.

[@walterdudedonny]

As a huge fan of Wilco at that time, I had my eyes out for their new projects and I followed the making of the documentary closely. I remember Sam had a blog about making it, essentially a diary. Did he ever publish that? I only knew Sam because his affiliation with Wilco.

[@jcjohncarter3]

Has Jeff Tweedy been on this show before? I know Jeff mentioned in his book that Sam didn't actually film the actual making of 'Yankee Hotel Foxtrot' but only filmed the demo portion, and also didn't dive into Jay's addiction issues which was ultimately the real reason behind his departure from Wilco.

[@jesseemullen]

Most of the demos were actually done with Ken Coomer in 2000. They were pretty close to finishing it when he started filming in January 2001. (They delivered it to Reprise in June of that year)

[@casperguylkn]

This is so untrue and unfair to Jay. The argument was edited and Jeff puking happened days earlier. It all made Jay look bad. Was Jay using drugs? Yes and so were others in the band and they functioned just fine.

[@patriciagrandjean8205]

@@casperguylkn Oh, please. Jay Bennett wasn't functioning "just fine." He was having boxes of drugs shipped in and creating even more anxiety for Jeff Tweedy than he was feeling already. I'm getting really tired of the Jay Bennett, "misunderstood genius" meme. Personally, I think he was very gifted but as a person, I wouldn't want to be around him for long. And I don't agree that "Where Are You, Jay Bennett" made him seem any better as a human being. But yes, his talents were celebrated more effectively. Personally, I think "I Am Trying to Break Your Heart" was great in that it shows what a crazy time making "YHT" was in Wilco's development--I didn't think anyone was a hero. You can tell by watching that Tweedy is close to unraveling, and Bennett contributes to that.

[@casperguylkn]

Made Jay Bennett a villian. Good job.

[@julioibarra7156]

One of the top music docs. Not all happy times making records

[@oliviagiles]

Holy crap Mr Jones, you are amazing!!!!! :)

[@SANTOMSTELLA]

He always reminds me of meet the millers. Lol.

[@davidbenson2224]

Figure it out, Sam! Great!

[@mnchls]

just now released that he's the same Sam Jones. damn!

[@That1Guy]

It’s been scrubbed from the internet. Even Disappeared from my iTunes purchases.

[@troy8420]

it's on vimeo

[@spacedoubt15]

All these cultured people in the comments and I've never heard of the band let alone the documentary. I don't live in the states is my only defense.

[@norasmith2474]

Even in the states Wilco is not a household name. They are popular and well known if you're into their genre of music.

[@bonvivantinsf]

Jason Sudekis is the luckiest bastard in history

[@silverfishla]

You basically killed Jay Bennet's career and made Wilco suck. Thanks Sam Jones.

[@AndySalinger33]

That documentary is one of the worst cases of a director completely shaping and controlling the narrative. He essentially destroyed Jay Bennett with editing flourishes. It was a one-sided, mean-spirited and successful attempt to paint Jay as the problem. I happened to rewatch it a few weeks ago, and it’s even more glaring than I’d remembered. Really disgusting.

[@duncansligh5822]

I think it just showed a handful of creative disagreements that served as an explanation as to why he was let go. And then it’s not like Jay did a great job of being graceful in that moment. He pretty much dissed that band to the camera on his way out. Jay was brilliant, and I think the doc early on showed his musical mind, but also showed that he was taking creative direction away from Jeff in a way that wasn’t productive to the band.

[@AndySalinger33]

@@duncansligh5822 I can see your points completely. And I really appreciate the civil discourse. Jay certainly didn’t help himself at many turns. It’s true. And I saw them live in bars with Jay, as well as seeing them live many times from the “Wilco” album, through to around “the Full Love”-era. They are certainly a different band without JB. I liked them a lot through those years, but I did sort of lose interest and stop really following what they’re doing. Tastes change, I guess. Nice talking with you. 👍😀

[@duncansligh5822]

You too! I appreciate your perspective!!

[@PRAGMAGICK]

aw shucks we got ourselves a family here! *I don't quote Raising Arizona with sarcastic intentions*

[@AndySalinger33]

@@PRAGMAGICK nice 😂😂

[@theoryofthemobius]

Two nights to get a two camera effect... yep, been there. It's how we get our chops.

[@bhotaling1]

This is great. I was hoping Sam would sit in the other chair.

[@eximusic]

Funny, I never put that together either (that this Sam Jones is the same on that made that documentary, which I own). Wow, I was always wondering who this guy was anyway.

[@brooklynboy1000]

jason did you get your salad dressing?

[@philipbell9301]

That movie made me completely dislike Tweedy, just reminded me of someone could crawl under your skin and then act like it’s your imagination. Bennet was the best arranger. Stuff is so boring and show boaty at the same time now.

[@bentolleson2585]

Never cared for Wilco. Jeff Tweedy hitting on Son Volt's girlfriend during the Uncle Tupelo days just turned me off concerning anything Tweedy would be involved in. That's just my opinion though.

[@blainebauman572]

Ben Tolleson Tweedy tells his side of this story in his book, it’s worth a read.

[@bentolleson2585]

Blaine Bauman thank you for the suggestion. I will look into it. Thank you sir

[@annabanna3024]

LoL. "Son Volts girlfriend" The Man behind SV is Jay Farrar. If you do your research the dude is a total asshole and was always extra shitty toward Tweedy back in the day. Sucks you turned yourself off to Wilco over something like that though. Especially since it had nothing to do with you personally and you don't really know what went on exactly. You really have missed out on a ton of great songs and a bunch of fantastic albums. 😕

[@patriciagrandjean8205]

You mean Jay Farrar, not "Son Volt." That's the name of Farrar's band.

[@Covid--ts5cw]

This is racist. 🇺🇸