Thanks to Sturgill Simpson and Internet Strangers, I’m Finally Living My Deadhead Dreams

17 years before Sturgill Simpson said that Jerry Garcia saved his life, I heard the word “Deadhead” for the first time. It was a word I didn’t know the meaning of until much, much later in my life, when “Ripple” was just another pretty song, one that had no consequential impact on a fourth grader. My parents had the entirety of Freaks & Geeks on DVD, which I devoured just as I had pored over my VHS tapes of Teletubbies, Scooby-Doo and the Cyber Chase, Spider-Man and Toy Story in the years prior. Summers back then involved a copious diet of Freaks & Geeks, NASCAR races and Cleveland Indians games, as my middle-childhoood came alive in the company of a working television set. At my grandparents’ house, I’d stumble through Stump the Schwab re-runs on ESPN Classic, scheming deeply about when my next opportunity to pop a Freaks & Geeks disc into the DVD player, which my parents taught me how to use solely because I wanted to watch the cancelled-way-too-soon show on repeat, would crop up.

Lindsay Weir (Linda Cardellini) is selected to attend a prestigious and competitive academic summit at the University of Michigan, but she isn’t sure she wants to go. Her guidance counselor, Mr. Rosso (Dave “Gruber” Allen), lends her his copy of the Grateful Dead‘s American Beauty. “Whenever I was stressing out, it always helped,” he tells her. “Are you a Deadhead?” a hippie classmate of Lindsay’s later asks her in the lunchroom, upon seeing American Beauty tucked under her arm. “Is it that great?” Lindsay asks her. “I wish I never heard it, just so I could hear it again for the first time,” she responds. The next day, she eats lunch with them and they tell her how incredible driving around and “following the Dead” is. “This one time, we were in New Jersey and it started raining right in the middle of the show,” one of them says. “So, suddenly, everybody goes running down to the pit and they start dancing in the mud. Then, the sun comes out, and there’s this rainbow right over the stage.” They invite Lindsay to come with them on their journey once school’s out, to follow them from Texas up to Colorado and see “nine shows in a week-and-a-half.”

At the show’s conclusion, Lindsay gets on a bus to Ann Arbor and, along with Kim Kelly (Busy Philipps), hops in their classmates’ Grateful Dead-painted van and, as “Ripple” kicks in, the “If I knew the way, I would take you home” line climaxes when Lindsay and her friends drive away into the great unknown. At age seven or eight, I was firmly in my classic rock era, but nothing beyond the AC/DCs and the Def Leppards of the world. Neither of my parents liked the Dead, either.

There’s a photo of a nine-year-old me in my childhood living room, decked out in a pair of AC/DC sleep pants and showing off my three-point football stance. In the background, the Freaks & Geeks DVD menu screen is on the TV. I cannot speak to why I loved that show so much back then. Maybe I loved it because my parents both loved it, and somewhere in the noise was a generational birthright being transmitted between kin. Maybe I heard that sweet, swet rock ‘n’ roll soundtrack, saw that one of the main characters was also Harry Osborn in the Spider-Man trilogy, and felt pulled into it. Maybe it was my body adoring something years before my brain would ever catch up. The characters were like me at various intervals of my life: I had a deathly peanut allergy; I am intersex; I started bands that never meant anything but still gave them names; I couldn’t climb the rope in gym; I quoted Caddyshack and thought Bill Murray was the funniest guy ever; I made grilled cheese sandwiches after school while home alone; my household was dysfunctional yet not broken; I thought Bob Seger & the Silver Bullet Band would make for great make-out music. It was all me and, even as my cells become newer and newer with each waking and dying day, it is all still me.

But the Freaks & Geeks finale, titled “Discos & Dragons,” felt far away from me for so long. For all of the ways the show, even in its most ‘80s-bound tropes, remained culturally present in 2000, 2007, 2016 and 2024, that last episode never clicked. I liked disco music, having spent so many summers dancing to it by the fire pit with a dad lost in his drink; Pokémon was to me and my friends what Dungeons & Dragons was to the geeks (John Francis Daley, Martin Starr, Samm Levine) 30 years earlier; No one around me was disappearing for a summer to follow a band plastered on T-shirts at Hot Topic. Upon properly getting into the Grateful Dead in high school, I quickly understood the significance of that final Freaks & Geeks scene. Lindsay bailing on her invitation to the academic summit to hear Jerry Garcia, Bob Weir, Mickey Hart, Phil Lesh, Brent Mydland and Bill Kreutzmann play nearly a dozen shows became a token of surreal, liberating precedent.

Across the prior 17 episodes, we watched Lindsay stumble through her junior year of high school without so much as a clue about what she wanted. Then, she finally makes a step toward taking control of her life, by taking a risk her family has conditioned her to avoid. I wanted something like that to call my own, so every time I went to record stores, I bolted to the Gs—desperately hoping that the clerk would put an LP in my hand that’d yank me out of the place I had called home for so long. When Walmart started selling a tie-dye shirt with dancing bears on it, I spent what little cash I had on it; I tried turning my pals on to Workingman’s Dead, but to no avail, not even when we’d get together and smoke cheap pot. It was all ephemeral, as Dead & Company had not yet started and it’d been almost 20 years since the Grateful Dead played their final show at Soldier Field in July 1995; Garcia passed away a month later; Weir, Lesh and Hart formed the Other Ones in 1998, only to change their name to the Dead five years later; then came offshoots like Furthur, the Rhythm Devils, Billy & the Kids, RatDog, Phil Lesh and Friends; in June and July 2015, Weir, Lesh, Kreutzmann and Hart held the “Fare Thee Well” shows commemorating 50 years of the Grateful Dead.

By then, it felt like my chance to live out a psychedelic whim just like Lindsay Weir did was all but impossible. I was in college and broke. Dead & Company would come to Cleveland and play shows at Blossom Music Center, but no one would take me to see them. It was like ships in the night, until I fell in love with a girl who hated the Dead and left my dreams behind—until she and I chased our favorite band, the Districts, around for a weekend, catching a couple of shows. I met a couple of kids from the East Coast in the front row, as they’d been following the tour on its way west. I’m still mutuals with some of them online, and we exchange likes here and there. 72 hours of music, driving, chatting, swaying and singing is all it was, but in my mind it was so, so much longer. It felt like the “oneness” that those Deadheads lionized in Freaks & Geeks.

In 2018, my partner and I went to our very first Mountain Goats show together at the Beachland Ballroom in Cleveland, Ohio, and waiting in line outside the venue was one of the most whiplash-inducing history lessons I’ve ever experienced. Fans of all ages were swapping war stories about their favorite shows, whether it was at the Earl in 2004, or the Farm Sanctuary in 2007—shows they’d not been to, but heard it online. When John Darnielle, Jon Wurster, Peter Hughes and Matt Douglas took the stage, a man next to us checked that his expensive-looking Zoom-brand audio recorder was working properly; to this day, the recording of that show still lives on the Internet Archive. I can still hear myself and a girlfriend I no longer know cheering and laughing when “Up the Wolves” starts playing. Some days, hearing those affections is the only way I can remember her voice.

Before the Mountain Goats show started, a couple next to us explained how they’d been tailing the band from Toronto and had plans of following them deep into the Midwest. The wife, an artist whose Instagram handle escapes me nowadays, made unique stickers for each gig and handed them out to those of us in line and in the crowd. A year ago, I returned to Beachland for a concert, and one of her stickers was still on a pole outside of the front door. I never knew Deadhead was such an elastic term, one that could be used to describe fandoms of a lot of bands. Even Taylor Swift, whose concerts nowadays can cost thousands of dollars to attend, have Deadhead fans. The Mountain Goats have Deadheads, as do Insane Clown Posse, Phish, Dave Matthew Band and, really, any active K-pop group. All of it felt so purposeful, even as I existed outside of it.

But in 2024, being a “Deadhead,” or an equivalent of that, isn’t entirely feasible for someone like me. Dead & Company have quit touring, though they have left the door open to play more shows—namely a residency at the Sphere in Las Vegas that stretched from May through August of this year. And it’s not like following indie musicians across the country is cheap. I’d considered doing it this summer with a punk band I like a lot, until I realized that, with gas prices, housing costs and editor responsibilities, taking a week to tail a band for the love of the game isn’t much of a luxury anymore. I know someone who went to over 20 shows during Harry Styles’s recent Love on Tour itinerary and hit multiple states and countries in the process—an anomaly that, in a post-quarantine culture, feels especially anomalous and especially privileged. If you are barely making a living wage, just getting to see your favorite artist once has a barrier to entry. Fiscally, a Deadhead-style of living could be completely extinct by 2030. We’ll all be clutching our copies of Nightfall of Diamonds a little tighter then.

It also doesn’t help that, after catching COVID-19 in December 2020, some of my longtime chronic illnesses were exacerbated into a pretty potent, always-present cocktail of discomfort. I can’t stand up for long periods of time, nor can I eat a lot of food in one sitting. It’s an outcome that’s broken romances and weakened friendships because of my medically-induced flakiness. I don’t know what it means to have a night out on the town anymore, nor can I really enjoy a trip anywhere—because my daily itineraries have to account for how quickly fatigue will wash over my whole body, otherwise I will come home and be sick for a week from pushing myself too far. All of the Deadhead potential those Districts shows stirred within me had been vanquished by the wicked that always stops to collect. I quit chasing what I could no longer reach toward.

Now, spending hours upon hours in a car and traveling from city to city for a two or three-hour concert, only to do it all over again the next day, would be detrimental. Once this all became a burden of my reality, for however much longer I am alive, I started listening to every Grateful Dead live recording I could get my paws on. The shows in Veneta and Philadelphia, in 1972 and 1982, respectively, quickly became favorites. But even then, combing through 30 years of shows left a vacancy in my soul. I could listen to those songs, but I couldn’t hear them.

I bring all of this up because, on his current Why Not? tour, Sturgill Simpson is healing the part of me that has so deeply yearned for completion. Beginning in August in San Francisco, California, Simpson has been traipsing across the United States and bringing 3.5-hour sets along with him, touring his new Johnny Blue Skies album Passage du Desir and touting a decade-long discography with a coterie of players who jam so tightly that every gig sounds as good as The Last Waltz. And, thanks to an app called Nugs.net and the goodwill of concert-goers who thought to tape the performances, I’ve been able to listen to every single Sturgill Simpson as if I was there humming along with the thousands of people you can hear hooting and hollering in-between every number.

Every morning, I press play on the show from the night before, letting Sturgill and the boys soundtrack my work routine all the way through lunchtime. His opening song changes nightly; he kicks things off with “Long White Line” once, only to shift into “Juanita” a day later. “Railroad of Sin” gets to bat leadoff for a show, but so does “Brace for Impact (Live a Little).” To open a performance at the Santa Barbara Bowl, Sturgill elects to play his beloved cover of When in Rome’s “The Promise,” which found a forever-home on Metamodern Sounds in Country Music. I lay in bed, laptop tented atop my chest, and comb through pages and pages of freelancer Google docs; I run a massage gun up and down my thighs; I rub testosterone gel into my shoulder blades; I drain my lymph nodes with a gua sha: “They say that joy is fleeting and pain is forever,” Sturgill sings, and it falls out of a Bose speaker a DJ sent me in a PR package. “How I wish that happiness left scars, too, just like you do.”

And just as the Dead had filled their setlists with cover songs—ranging from Marty Robbins’s “El Paso,” to Bob Dylan’s “It’s All Over Now, Baby Blue,” to Mitch Ryder’s “Devil with a Blue Dress On”—Sturgill Simpson lets his band’s renditions of the Allman Brothers Band’s “Midnight Rider,” Procol Harum’s “A White Shade of Pale,” the Doors’ “L.A. Woman” and Roy Orbison’s “Crying” enrapture the audience. He sings his new song “One For the Road” and it dissolves into Prince’s “Purple Rain.” And not for a moment does any of it sound like anything but Sturgill Simpson or Johnny Blue Skies. And there I am, watching the pollen kick up into the air outside my screen door and hanging onto every note.

After Sturgill’s show at the Roy Wilkins Auditorium in St. Paul, Minnesota on September 25th, my social media feeds were bursting at capacity with iPhone-shot videos of him and his band (Laur Joamets, Kevin Black, Miles Miller and Robbie Crowell) blazing through the classics, like “Turtles All the Way Down,” “A Good Look” and “Living the Dream.” His performance of “Time After All” is especially gentle but rousing, a proper come down after “The Promise” and “A Whiter Shade of Pale” melted into one another. One user on Twitter/X even went as far as posting a long thread of every song he captured, letting everyone know that, for one night, one-half of the Twin Cities was the center of the whole goddamn universe. And there I was, procrastinating on my homework and following along with every tweet added to the thread. And then I logged into my Nugs.net account 12 hours later to hear all of it again.

Before I grew up on Freaks & Geeks, I grew up on country music. Ask my mom what my favorite song back then was, and she’ll be sure to mention something about a home video of me singing Alan Jackson, or she’ll bring up how I used to play Diamond Rio’s “Beautiful Mess” over and over until my portable CD player broke. Then, though I rarely like admitting it, I’ll reveal that my first-ever concert was a Brad Paisley performance at a country fair in Ohio in 2003. It was the music my grandparents played in their car and in their garage and in their living room. We’d take all the winding West Virginia roads and the local country station would dip in and out, as the Devil’s Elbow turned my Coca-Cola flat. My mom was at that legendary Kenny Chesney show at Cleveland Browns Stadium, the one where all of the bathrooms in the venue were out-of-order. I can picture a seven-year-old me watching CMT’s music video countdown and shaking my rump to Trace Adkins’s “Honky Tonk Badonkadonk.” Once upon a time, I was obsessed with Joe Nichols’s “Tequila Makes Her Clothes Fall Off,” and I used to howl along to Toby Keith’s “I Love This Bar” as if I was a binge-drinking third grader.

But my beautiful love-affair with country music came to an end when it was time for me to carve out a taste of my own, when the Blake Sheltons, Jason Aldeans and Luke Bryans of the world entered the genre’s pantheon and ruined it, when my grandparents kept getting sick and their stereos were on less and less. But then Sturgill Simpson came around—or into my view, at least—in 2016 and released his third album, A Sailor’s Guide to Earth, and I watched him sing “Call to Arms” on Saturday Night Live almost a year later. And then he won a Grammy Award for Best Country Album, back when I still voluntarily watched the Grammys, and I began to believe in the countrypolitan pride that beckoned once my fingers to rewind that Diamond Rio CD. And I kept it all to myself, even though millions of other people loved Sturgill’s work. But nobody that I knew listened to him, so I toddled in my own cosmos of reptile aliens made of light. I believed in a kind of living where love’s the only thing that’ll ever save it. Many called Sturgill Simpson the savior of country music; I’d say he’s more of a guardian of memory. He makes the kind of music that lets you know that parts of yourself are worth remembering—a kind of music you can lay down and hear every second of.

I don’t go to concerts very much anymore, and I’ve probably only stayed for an entire show twice in the last four years. My body is falling apart, but the music still glows within me, so I go to the venues even if I know there’s an expiration date idling. But none of that matters when I’m in the company of Sturgill Simpson in 2024. I can check in and check out his shows as I please, or I can linger in the performance from the first note to the last lick, from “Juanita” until “Jupiter’s Faerie.” I don’t even worry about whether he’s making a stop in Ohio on this tour or not; it wouldn’t matter anyway.

The theatrics—which, in Sturgill Simpson’s case, are just hard-nosed guitar notes strummed with a certain level of Kentuckian panache—are life-affirming even as they trickle out of my phone’s speakers, as I exist and I ache and I sing along from someplace hundreds and hundreds of miles away. I sleep in a part of a house that was once an indoor patio where my grandfather would sit, listen to country music radio and watch semi-trucks thunder down the highway outside. Whenever Sturgill kicks into “Scooter Blues” and puts on his Jerry Reed hat, I rise from my bed and do a shuffle in the daylight leaking through the tressing blinds blackening out the room, because I know my grandfather would have enjoyed hearing a song squeal like this.

It’s not lost on me either that, as Sturgill Simpson’s reverence for music-making and playing were growing thinner in recent years, it was his preparation for the Dead Ahead festival, where he had to learn quite a few Grateful Dead songs, that reinvigorated his craft. “It’s almost like I could anticipate where Jerry [Garcia] was going,” he told Uncut. “And it was because Jerry played folk, country, bluegrass and blues, the same way I play guitar.” Now, I’m not explicitly comparing Sturgill Simpson to the Grateful Dead, but there is a reason why, in an age where 45-minute sets are becoming as common as they are preferred by artists of my generation, there is something profoundly romantic about a veteran picker like Simpson spending 1/8th of his day on-stage at auditoriums, theaters, arenas and amphitheaters in the cozier, familiar parts of America. It feels like, dare I say, a “oneness.”

As fate would have it then, there is something divine about these parts of my world colliding now—Freaks & Geeks (the series premiere just had its 25th anniversary), the Grateful Dead, chronic illness and the Sturgill Simpson of it all. Years ago, I found it cruel that I’d never be the Deadhead my favorite show so very obviously hoped I would become. It’s like that scene in Uncut Gems, where Kevin Garnett asks, “Why the fuck would you show me something if I couldn’t have it then?” but personified into some sick and demented reality augmented by my worsening health. But the things that color your purpose shall always remain, and Sturgill emerged this summer under the name Johnny Blue Skies—billing his records and shows as such—and resurrected all of that loss. In this life, his music argues, I too can turn the volume up like I’m ready to pull all the garage walls down, even if I haven’t yet lived through the love I’ve so hopelessly thrown my beliefs behind. There is joy, he contends, in unfulfillment. Why spend every day listening to a less than HD recording of a concert I wasn’t even present at? Maybe I love all of this so much because it feels nice to be a part of something, even from a distance. There’s an entire universe in my phone; this body’s meanness softens for the 180 minutes that Sturgill Simpson is singing.

I think a lot about how, because somebody else loves the Mountain Goats so much, there is a part of me and someone I loved dearly that is forever accessible on the internet. And anyone can click play and feel all of it even when I cannot muster the courage to do it myself. You can’t always hear those moments during live recordings of Grateful Dead shows, but you can imagine that, somewhere in-between the band playing a resounding take of “Bertha” and Bob Weir lamenting the Oregon heat, two people exchanged a look or a laugh with each other that neither of them can now access. After the conclusion of “Turtles All the Way Down” at the St. Paul show, Sturgill Simpson lets out a deep exhale and a woman in the crowd cheers louder than all of the clapping hands combined. It’s been two weeks since that gig, but I’m still thinking about her and how, when that same song ends in another state one, or six, or 12 days later, it is absent from all the noise. That woman will never cheer like that again, but the rest of us get to remember it for her.

Because sometimes, it just takes a couple of hippies saying, “American Beauty, that is a great album, man,” to you in the school cafeteria at lunchtime, or maybe it just takes a stranger on the internet uploading audio from a Sturgill Simpson concert onto a weed-inspired phone app. Or, just maybe, all it takes is the belief that I can make love-struck magic with thousands of people who, like me, so badly want to take control of their own lives. A wise man once sang, “Would you hear my voice come through the music? Would you hold it near as it were your own?” and, when I lay in bed—gut turned inside-out and back muscles knotting into an unforgivable grief—I sing, “I believe that I found God about the same time that I found you,” out to no one, with the hope that everybody hears it.

Matt Mitchell is Paste’s music editor, reporting from their home in Northeast Ohio.