Futureproofing #21: The Grateful Dead and the pursuit of imperfection
Why I love the infamous jam band, after a remarkable 60th anniversary celebration summer.
Edited by Tom Gledhill
Earlier this year, The Grateful Dead released a 60-CD set called Enjoying The Ride, celebrating the 60th anniversary of the formation of the group. A 60-CD set might seem ridiculous, but it's part and parcel for a band utterly obsessed with its own history, with multiple series already dedicated to releasing live recordings from throughout the band's existence. As part of my enduring (but sometimes on-again-off-again) Dead fandom, in July I decided to listen to all 60 discs.
The box set focuses on concerts recorded at venues most associated with the Dead: Winterland, Boston Garden, Red Rocks, Madison Square Garden. Like so many of the Dead's archival sets—like the time they released every concert from their 1972 European tour—it's a demanding proposition, a warts-and-all look at a band that doesn't highlight its strengths so much as its tenacity and willpower.
The Dead weren't about perfection. Instead, they had a drive to constantly explore, to find new wrinkles in their music, and to make people happy, even when the members themselves were at their lowest physically or mentally (which you can hear frequently, especially in the later years of the band before leader Jerry Garcia died in 1995). While Enjoying The Ride occasionally felt like a chore to get through, especially its dicey stretch through the mid-'80s, it also reminded me why I love this band so much. The Grateful Dead were and are still a living, breathing project, whose evolution anyone can trace back to the beginning thanks to the meticulous archive. The band also still exists in various forms: new bands and offshoots grafted from old configurations, like a rose garden that survives floods, droughts and heatwaves.
For those who don't know much about them, the Grateful Dead were forever associated with their live shows, not their tepid studio albums. (Their 1970 twofer Workingman's Dead and American Beauty are among the best classic rock albums ever, though.) Fans recorded Grateful Dead concerts with amateur taping setups and would trade recordings of the shows, activities later allowed and even encouraged by the band, with sections set up at shows for people to make their own tapes. Huge networks of traders popped up over the course of the band's history until it was a sort of cottage industry all its own, which now means the majority of the music ever played by the band is easily available on the internet.
Played live, even rootsy folk songs or hokey covers could come alive, spreading out into loose, improvised jams that spiral out fractal patterns. Sometimes the Dead could pack a world of musical ideas into seven or eight minutes. Other times they might ride one phrase or motif out for over half an hour. Their jams were the stuff of legends, and of jokes. It was genius to those in on the fun and unlistenable noodling to everyone else. The band rarely played one of their longer jams the same way twice, which is why fans would shove their own lives aside to follow the Dead around on tour. Comparing setlists, trading recordings, and arguing over the best versions of different songs are as much a part of being a Deadhead then putting on a record or going to a show. (It's not that much different than listening to DJ sets online, or booking a Ryanair flight to see your favorite DJ in another country for a weekend.)
But there's another reason for their enduring popularity, beyond the extensive archive and the nerdery that comes with it. Drawing from a repertoire of original songs with lyrics written by actual poets, and an arsenal of covers that ranged from Bob Dylan and Merle Haggard to pre-war folk songs, the Dead are in some ways the ultimate Americana band. Their music combines traditions from across the heartland, rooted in bluegrass and inspired by jazz. Though they came up in a San Francisco scene that included groups like Jefferson Airplane and Big Brother and the Holding Company, they actually started as a jug band. Jerry Garcia's first instrument was the banjo, which informed his eventual trademark guitar solo: fast, zippy, melodic, (literally) high-strung.
The band were also students of John Coltrane and Miles Davis—in fact, Davis's electric band opened for the Grateful Dead in April 1970—and they were as connected to psychedelic rock as they were fellow roots revivalists like The Band, all at once. They could play a set of quick country and pop-rock songs followed by a set where they go 40 minutes deep on one song, or string eight songs together into two hours of non-stop improvising. What could be more American than that: combining free jazz with folk, country, rock and blues, connecting traditions from across rivers, coasts and invisible cultural barriers? This is what makes The Grateful Dead such powerful unifiers. It's why the band rules the roost with anarchist hippies and hypercapitalists alike, why Major League Baseball has Grateful Dead nights and Online Ceramics makes a killing off making Grateful Dead merch. They appeal to everyone.
Well, sort of. The very idea of the Grateful Dead, and especially the aesthetic, has a timeless cool about it. Mainly because they never tried to be cool. But the actual music is probably an acquired taste for most people. Still, it's hard to imagine someone putting one of their original live albums—like Europe '72 or the pivotal Live/Dead—and not finding something to enjoy.
There's the "Dark Star" from 1969 on Live/Dead, the definitive version of the band's greatest jamming vehicle, which would take them to the furthest reaches of their sound. It was their own In A Silent Way, music that transcended genres and context to become a freeform cloud of sound. And on records like Europe '72, there are incredible versions of "Truckin'," one of the group's most famous anthems, and "Jack Straw," one of the band's country epics told in snatches of windswept imagery and stitched together into a dreamlike suite of passages that range from lilting to amphetamine jittery.
Those, however, are curated (and studio overdubbed) albums for mass consumption. Box sets like Enjoying The Ride, or archival series like the legendary Dick's Picks, reveal the grit and hustle behind a band known to play for three to four hours every night. There are bum notes, missed lyrics and fudged harmonies, but these moments—or even whole substandard concerts—made the good nights even sweeter. It's just that with most bands, you never hear the subpar bits unless you were there to witness them yourself.
There's a certain pleasure in hearing a not-so-great rendition of a song only for the band to explode into technicolour during the transition to the next. Or in hearing one of the guitarists or keyboardists stumble on a phrase that lights a fire under everyone else. The occasional struggle is a reminder of the humanness that makes them more relatable than most other famous classic rock bands. In the '80s and onwards, as Jerry Garcia's health worsened, it was often said that if he had trouble singing, his guitar playing would be incredible, as if he were speaking through the strings instead. I'm inclined to agree, which raises an unusual question: why would you purposefully want to listen to a band when they're not at their peak?
The answer is because of a lifelong connection that can feel unusually personal, like you've been there with them the whole time. How many other groups are there where you can listen to them night-in and night-out and hear something different? Where you don't have to return to the same studio recordings but can instead choose from 200 different versions of a song, all played a little differently? What other band can you love at their worst, and love even more at their best, and appreciate the good times through the lens they give you of the bad times? (This idea describes jam band culture at large, but The Grateful Dead's music is actually good, and most other jam bands… aren't.)
I felt this connection the first time I saw Dead & Company, the band that cofounder Bob Weir has led with original drummer Mickey Hart since 2015 (featuring John Mayer on guitar and vocals in place of Jerry, and a handful of other musicians who have been in the greater Dead orbit since the late '90s). At their best, the band is a faithful continuation of the legacy, even if it's something of a tribute act. My first time seeing them play at Dodger Stadium in 2022, I was locked in in a way I've never really felt at a concert or a DJ set. Just utter captivation, watching and listening to the music breathe and grow, surrounded by people of all ages who were just as excited and openhearted, and who have all had their own personal, decades-long journey with the Dead.
That first show I saw was amazing, in spite of some of the worst songs in their repertoire towards the end (covers of "Dear Mr. Fantasy," and, god help us, "Hey Jude"). To me, it was basically perfect—I even finally had the universal Deadhead experience of sitting through a song I didn't like, in person. The second time I saw them, a year later, things were weirder, and a bit spacier. I wasn't as bowled over, but it was remarkable seeing an aging hippy legacy band play music that was somewhat confrontational, or at least confrontationally strange.
And then, on the first weekend of August 2025, the band took over Golden Gate Park for a 60th anniversary celebration that many assumed might be the end of the ten-year Dead & Co project, as founding singer-songwriter and guitarist Bob Weir starts to look visibly worn. Anticipation ran high: tickets, which were over $600 for the whole weekend, sold out almost instantly, and San Francisco repainted a few city buses to celebrate the band's legacy in the city, as well as the tens of thousands of fans descending on the park for the weekend. The shows were being streamed live (also for a hefty price tag), which meant that it was more of a global event than a localized Bay Area one.
I organized mini-watch parties for two of the three nights they played. I was stoked. And in the end, they kind of sucked. It was brutal to watch one of my favorite bands embarrass themselves a little, during shows broadcast around the world. The second night had some stronger moments, but on the third night, the band rarely caught fire, lacking the chemistry of the group at their best, and with some individual performances so poor that it was hard not to find it distracting. But I still had fun. It was exciting to try and predict which songs were coming next, what they might play on which night, and of course, that feeling when the band did catch fire, like on a particularly exciting rendition of the "Help On The Way" > "Slipknot" > "Franklin's Tower" triptych they've been playing since 1975.
The unpredictability is key, and so is the trial-and-error process. Discussion threads and forums were full of people arguing about those Golden Gate Park shows: they weren't the best that weekend, but we were lucky to still have this music. How dare we criticize? But also, the band used to criticize themselves, and they know they have off nights. Part of being a Deadhead is making fun of the band or being honest about when they're not so hot. Back and forth, ad nauseum. But it made me realize that being a Dead fan isn't just about enjoying the music—it's about living it alongside the band. Dare I say, it's about enjoying the ride.
This is what makes the band such a force: you can never really get sick of them, or at least I can't. There's so much variety even in the band's most bog standard performances. You can listen to a string of concerts all in a row from peak years like 1972 or 1977 and experience vastly different performances.
A lot of it feels like circumstance and practice. The band aren't the most technically skilled musicians in the world, but they had enough creativity to make each night sound different—to find new pockets in a song they've played over 1,000 times. And they're still doing it 60 years later, still trying to forge new ground, even as the main players approach 80. Like the Sturgill Simpson-assisted "Morning Dew" from the Golden Gate Park weekend, which is among the best versions of that song I've ever heard.
So I will always be a fan of the Grateful Dead and its offshoots, even though sometimes it can be embarrassing—either because of the hippy associations, or the boomerness of it all, or the fact that the band can be embarrassing themselves. (No one needs to hear John Mayer and Bob Weir halfheartedly cover a Sam Cooke song.) I will always fly the flag for them, because they capture what I like most about all music, which is also what drew me to electronic music: unlimited possibility. Dense layers of references folded back into each other. Endless remixing of familiar tropes, songs and phrases. A feeling that no matter how great the past was, the future still holds more. And the idea that every night can bring something completely new, even when it's deeply familiar. I will always thank The Grateful Dead for teaching me the joy of spontaneity, and teaching me, as a kid who never went to anything, about why people go to events and experience music communally.