There’s a scene in I Am Trying to Break Your Heart: a Film About Wilco, the 2002 documentary about the making of Wilco’s Yankee Hotel Foxtrot that lives rent free in my head. Wilco’s singer/songwriter Jeff Tweedy and multi-instrumentalist/detail wizard Jay Bennett are sitting behind a studio console working on the mix for an album that has taken a lot longer to come together than either of them expected when they have a misunderstanding about how to transition one song into another. Tweedy expresses a general idea of how he wants the transition to occur, but Bennett insists on describing in excruciating detail the different ways to make it work. It’s a brutal two-minute clip. You can see that Tweedy is done with the conversation almost as soon as it has begun, but Bennett won’t let the subject die, and insists on not only explaining the alternative ways to solve this particular problem, but making sure that Tweedy absorbs everything he’s telling him. In the very next scene, Tweedy throws up in the toilet from a migraine and then returns to the studio, where Bennett continues harping on about the transition. 

After they finished the album, Tweedy fired Bennett from Wilco. 

 

Elsewhere in the documentary, Bennett is shown jumping from instrument to instrument, ripping a hot shit guitar solo, and helping orchestrate the brilliant collage of sound that makes Yankee Hotel Foxtrot Wilco’s most beloved album. He wisely says that every song (presumably that Tweedy) writes is a folk song, so the band has to rely on their arrangements to differentiate them. Despite its arduous birth, and a ridiculous music biz situation that saw Warner drop Wilco and then re-sign them under their own subsidiary label (effectively purchasing their album twice), YHF brought Wilco to a new level of stardom. Much of that credit should go to Bennett and his meticulousness. After firing him, Tweedy had to hire two people to replace him. 

 

I would’ve canned Bennett, too. 

 

This week’s column is about being cool, being a good hang, being someone that other people want to be around. 

 

When you’re splitting a couple hundred bucks a show, it’s much more valuable to have someone in your band who’s proficient at their instrument and can take or tell a joke than someone who’s a virtuoso who can’t recognize one. While I’m sure there are massively talented people at the upper echelons of the music business who are allowed to be staggeringly off-putting, if you’re playing with the hoi polloi, you should be able to mix with them. In most cases, having superb chops will not make up for a dogshit personality. 

 

DO YOU SUCK?

 

If you find that your gigmates aren’t calling you back, that people try to squirm out of conversations with you after shows, and that you keep getting kicked out of bands despite being the “best goddamn player” in them, you might have to work on your personality. Here are some telltale signs (and some strategies on how to improve). 

 

YOU ARE A DOWNER: 

 

Do you love nothing more than greeting people with a complaint? Do you love bitching about a venue, your set position, the other bands on the bill, your audience, how early you have to get up in the morning? Do you think of life as a series of obstacles to whine about? Well, good news: nobody gives a shit, so you can stop. 

 

Here’s how I see performing: it’s a privilege to entertain people. Screw on a happy face. Remember how badly you wanted to play for people when you first started out? A lot of people want to do exactly what you’re doing. Don’t forget that. Don’t take it for granted. 

 

Also: I get that you’re depressed. We all are. It’s 2025 and the world is going to turn into a fascist cyberpunk dystopia before it burns up. But if you try to put positive energy into the world, you will see it return.

 

Also II: Go to the doctor. Try out some meds. I hate that big pharma is an industry too, but SSRI and Strattera are better for you than booze and coke, and Johnson & Johnson is still less evil than the Sinaloa Cartel. 

 

Also III: It’s fun to gossip. But you gotta be funny while you do it, or you’ll just suck to be around. Misery may love company, but nobody even likes misery. 

 

One last one: Pay attention when you’re talking to someone. Are you talking to them or at them? Do you remember the last thing they said, or do you only pause when you need to breathe. I’ve a couple people in my life who I might otherwise have a good time with, but I stick to small talk with them because I don’t want to hear a goddamned Ted Talk. 

 

YOU ARE PRETENTIOUS: 

 

You got a Master’s at Berkeley. You know the difference between a phrygian dominant and a harmonic minor scale. You need to let everyone know they said “sharp” when they meant “flat.” 

 

It’s a buzzkill when I’m explaining something to you and you’re correcting me on my terminology. It’s as if you’re reminding me that you’re smarter than me, even though you literally don’t know how to play what I’m showing you. 

 

Look, I get it. Music school is fucking expensive, and it’s bullshit that your well-trained mind is splitting $98 with my stupid head, but music is experienced as sound, not as letters on a page. If you spend more than 1% of band practice arguing about theory, you’re killing me (which means you’re actually killing yourself). 

 

Also: I know many of these personality tics can be chalked up to the spectrum disorder that so many musicians have self-diagnosed. To my autie readers, I would suggest that you treat personality practice like any other. In addition to watching Youtube videos on running the phrygian dominant and harmonic minor scales, I would suggest looking up videos on how to relate to people, how to make friends, and how to work as a team. The internet has been great for musicians as well as for people who’re neurodivergent (which is almost all musicians). 

 

YOU ARE AN ADDICT: 

 

It’s a given, even in today’s more straight-laced era, that if a musician is onstage, there’s a good chance there’s something dancing along with them in their bloodstream. Almost every musician I know either likes or liked to mix it up with chemicals. (Many of those who “liked” it had to stop because they liked it too much.) But when you start missing things, it’s time to either pull back or stop altogether (note: depending how hard you go, you may need to detox before quitting). 

 

Drinking and drugs go with music like guns and crime. They might make the job seem easier, but they for sure make it more dangerous. I’m not only talking about overdoses and vehicular manslaughter either. This article is about social graces, and when you’re loaded, you have fewer of them. If you’re rude or disgusting to the wrong people, it might cost you gigs, audiences, or, potentially, a career. It’s also really hard to shake a reputation as a booze bag. People will put up with you as long as you’re reliable, but once you fuck up, they’ll blame the booze, even if it had nothing to do with it. 

 

Also: a word about quitting. If you’re thinking about it, you should probably do it. 

 

Also II: Being obliterated or shitfaced drunk in public is gross after 30, and being heavily buzzed in public is gross after 40. Ironically, a lot of people drink to feel more mature, but the only people who can actually pull off public intoxication are girls who show their boobs for mardi gras beads and frat boys who practice kissing each other. 

 

Also III: I do want to make the point, though, that I’m not anti-intoxicants. Most bands’ biggest draw is selling drinks, not tickets. And the best audiences are usually pretty well-lubricated.  

 

YOU ARE A RACIST, MISOGYNIST, AND/OR HOMOPHOBE: 

 

C’mon. Don’t be that. We’d be stuck playing oompa music here in the States without contributions from girls, gays, and the melanin-enriched. 

 

This has nothing to do with politics. This has everything to do with not being an asshole. 

 

YOU ARE AN ASSHOLE: 

 

Some people aren’t on the spectrum. Some people are just fucking dicks. 

 

I think there’s something about the amount of alone time that goes into becoming a good musician that can make a person feel that what they do is more important than what others do. 

 

And there’s absolutely a correlation between narcissism and the desire to make everyone look at you while you talk into a microphone. The best singers I know are aware of narcissism’s power, but also intimidated by it. Just because you feel you have something to say, doesn’t mean it’s something worthy of broadcasting.

 

A caveat: The thing is that, yes, if you are really good, you can get away with being a dick for a while. But you better be really good. And you better be pretty funny. 

 

YOU ARE A PSYCHO, RAPIST, THE ANTICHRIST: 

 

Fuck off.

 

Scenes are getting better at flushing these cancers out, but some of them are buried deep. Some of them own venues, allegedly. 

 

YOU ARE A CREEP: 

 

Just tell the 18-year-old with the breathy voice that she had a good first show. Don’t offer to be her ambassador to the local music scene. (Also, do you really think she’s going to have sex with you? And let’s say she does, how do you think that is going to go? Fucking yuck.) 

 

Men vastly outnumber women working in the music industry, and you’ll only keep driving that number up if you gate-keep or creep on the women already here.

 

Besides, we need more women in music. In case you aren’t aware, the more women perform, the more women will watch. The more women watching, the more men will watch. More women equals more audience equals more than $98 split four ways.   

 

YOU ARE WEIRD: 

 

It happens. Not everyone fits in. A music scene can feel cloistered, like some version of high school where every classroom is a dimly lit bar, the bathrooms have stickers all over the walls, and the cafeteria serves lunch at 8:45 PM – chicken fingers, french fries, and whatever well two-part cocktail a blue ticket buys. Bands talk, some people are still mean, some things never change. 

 

The truth is people get into music for different reasons. For every person who wants to share their soul with the world, there’s a keyboard scientist who wants to have their explorations in FM synthesis incorporated into a song. 

 

My advice to people who are weird is to get good. It’s really hard to kick someone out of a band for being awkward when they have the material down. 

 

CONCLUSION: 

 

I think the craziest thing about having a dogshit personality is that people won’t tell you. They’ll just stop calling you. In medium-sized cities the pool of good players isn’t infinite, and the scenes themselves are actually quite small, so your reputation, as it is, gets around. 

 

YOU DON’T WANT TO/CAN’T CHANGE YOUR DOGSHIT PERSONALITY:

 

Sly Stone did hard drugs for over fifty years and quit. You can probably change. But let’s say you don’t. How can you still be in bands?

 

  1. Be the Best Player in Town: This is America. We say we’re a democracy but we’re actually an oligarchy run by rich people and celebrities. If you’re a celebrity, you can be all kinds of dogshit. 

 

  1. Be Rich: One of the hardest parts of getting a band off the ground is having a place to rehearse and equipment to record with. If you pay for all the stuff, your band members will be much more likely to put up with your dogshit personality. You can also bribe them with free beer, weed, and pizza. That alone will probably buy you six months. 

 

  1. Get Gigs: Hustling for gigs is hard and most people hate it, but a band without gigs is like a relationship without sex. And just like a person will put up with a trash personality for some bomb dick/pussy/whatever, a band will put up with your lousy personality if you score some dope stage time. 

 

  1. Do the Grunt Work: The member who handles a band’s social media, bookkeeping, or quartermaster duties will always get an extra allowance for their personal picadillos.

 

—

 

Towards the end of I Am Trying to Break Your Heart, an interviewer asks Tweedy what he thinks about separating from Bennett: “I think Jay’s contribution to the band, over time, and our collaboration, was important and was valued. As for the circumstances surrounding him leaving, I think that’s really up to Jay to define. As far as my feelings about it: I couldn’t be happier.”

 

In 2023, Jeff Tweedy and Wilco released their 14th album Cousin. I’m sure they’ll have another one out soon. They’ve had the same line-up since 2004. 

 

In 2009, Jay Bennett died suddenly from an accidental overdose involving a fentanyl patch he was wearing to combat hip pain that required surgery. Since parting with Wilco, released five albums, but is still best known for his work with the band that kicked him out.