Wilco’s Sky Blue Sky Was a Music Festival Even Chris Black Could Love

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I have never been that interested in music festivals. I prefer to see bands in dark clubs after having a sensible dinner. The idea of standing in the midday sun in a giant field (or worse, a concrete parking lot) to watch a band that normally plays at 9 PM hit the stage to sweat it out at tea time just never sat right with me. I first encountered this at Warped Tour in 2006, when Cartel, the band I managed, played in the parking lot of the Lakewood Amphitheatre in Atlanta. Enduring Motion City Soundtrack with nothing but Monster Energy drink in the cooler in Southern summer heat is a fate worse than jail. It made me feel old, and I was barely in my early 20s. I have only been to a few festivals since, mostly because How Long Gone was booked to perform.

I recognize that festivals are a necessary part of the modern music business. Economically, they are one of the few places where artists, promoters, sponsors, and platforms all win at once. Artists get meaningful fees and merchandise sales. Brands get captive audiences and lifestyle associations. Fans get the illusion of community in an otherwise atomized culture. Everyone agrees to the deal for a weekend. In a business where recorded music barely pays, festivals are where scale, urgency, and money actually converge. Most importantly, festivals supply meaning. They provide physical presence in an era of parasocial everything.

Last weekend, I was in Mexico, at the Hard Rock Hotel Riviera Maya, for the fourth edition of Wilco’s Sky Blue Sky Festival. We were there to do a live How Long Gone podcast on Sunday, but I wanted to go down on Thursday to see friends play. The lineup was stacked for someone with my tastes: Wilco headlined 3 of the 4 nights, Waxahatchee, MJ Lenderman & The Wind, Sno Caps, The Jayhawks, Yo La Tengo, Golden Smog, and Dinosaur Jr all played. The hotel was psychedelic to say the least—a sprawling property littered with dusty rock memorabilia, Led Zeppelin lyrics affixed to walls, and a truly insane Brett Michaels suite that I only heard tales of. The gym had a full wall-sized photo of Britney Spears next to the free weights. My room had bright blue walls, a giant silver headboard with an embossed pattern that resembled a Tommy Lee-esque tribal tattoo, and a mural of a blonde woman wearing a top hat smoking a cigarette Slash style while shredding on a Les Paul. I was sure I had made a big mistake.

I started to get the hang of the place. I have never been to anything all-inclusive in my 43 years on planet Earth. I am happy to pay (sometimes overpay) for what I want when I want it. Luckily, I had some Sky Blue Sky veterans give me tips on what food was edible and what I had to absolutely avoid. The first day, I was in a terrible mood—the flight felt long, the Cancun airport is always hell, and the hour-and-fifteen-minute Sprinter ride to the hotel is the last thing anyone wants to do. Seeing J. Mascis from Dinosaur Jr. walking around with a snorkel did help, though.

There was so much to make fun of. I kept a running list of all the t-shirts I saw. I was gathering material for our show on Sunday afternoon, ready to BBQ this whole fucking thing, but something happened on Saturday night. Wilco, a band I have deep respect for, was on stage for their headlining set. The weather was perfect, and they played “Passenger Side,” an old song from their album A.M., which came out in 1995. I was standing at the front of house, and as I looked around, something clicked. Next to me were people probably a little younger than my parents; they were both wearing Wilco shirts and singing along to every word, just like I was. These people aren’t in the music business; they don’t read Pitchfork, give a fuck about Spotify streams, or debate the merit of Geese on Reddit threads. They were people who probably lived in the Midwest suburbs and planned this vacation a year ago. They simply love the music, and I was earnestly moved. When you do this shit for a living, you forget that the whole point is just to enjoy it. So I did. I stopped being a cynical dickhead and watched Golden Smog from a dock while the rest of the crowd stood waist deep in the ocean, beers in koozies, wearing long-sleeve sun-reflecting fishing shirts. I stayed up until midnight to see Michael Shannon and Jason Narducy perform an amazing set of R.E.M covers. I didn’t think again about how the people looked or where they came from. I just had fun with my friends.