Grateful Dead, Sly and the Family Stone, Joan Baez, Kacey Musgraves, Ezra Koenig of Vampire Weekend and Janelle Monáe

Recasting Woodstock's Original Lineup With 2019 Artists

Due to a whole litany of legal obstacles, funding issues, and misguided decisions far too numerous to recount, an official 50th anniversary celebration of the Woodstock Festival won’t be taking place this year in New York State, Maryland, or anywhere else. The demise of Woodstock 50 is a shame, not just for the organizers and artists who hoped to make it happen, but also for the fans who hoped to celebrate this incredible watershed moment in American history.

But then again, how reflective was this proposed mega-fest to the original spirit of Woodstock in the first place on purely musical terms? The original Woodstock was a cutting-edge lineup, wholly reflective of what was actually taking place in the counter-cultural world of music in 1969. It included live dynamos like Jimi Hendrix and The Who of course, but also largely unheard acts just about to break through like Santana and Mountain, as well as engaging left-turns like Tim Hardin and Ravi Shankar. It also had several zeitgeist riders like Jefferson Airplane and Creedence Clearwater Revival.

If you were to try and assemble a modern-day lineup of Woodstock, reflective of the 31 different musical artists who hit the stage at Max Yasgur’s farm that warm August weekend five decades ago, it would probably look a lot different than the lineup that original organizer Michael Lang put together for Woodstock 50. Taking into consideration artists who were at similar points in their career (and/or occupied similar space in the cultural landscape) to the original acts on the bill, as well as the role those ‘69 artists ultimately played at the seminal event -- we’re not necessarily just looking at one-to-one soundalikes here -- this is what it might actually look like. 

Miguel for Richie Havens

Richie Havens wasn’t supposed to open Woodstock, but the snarl of traffic leading up to the site in Bethel made him a necessary fill-in for that role. He certainly wasn’t supposed to play for over two hours to buy time for some of the other acts like Sweetwater to make it through the morass of people. But Michael Lang and company knew they could rely on an artist with as much charisma and dexterity as the Greenwich folkie to fill a necessary block of time. Another artist with that kind of talent these days? Miguel. The L.A. R&B singer-guitarist is as reliable, crowd-pleasing, and eclectic a festival act as there is today, and would certainly more than kick things off with a bang, keeping the party rolling for however long the organizers might need him to go.

Haim for Sweetwater

Haim would be prime stand-ins for this sunshine-y band from Los Angeles, especially if they capped their set with their recent, sepia-toned banger “Summer Girl.”

Fleet Foxes for Bert Sommer

Bert Sommer specialized in the kind of lush folk music that Fleet Foxes have made their bread and butter across the last decade and change. Tell me you can’t hear Robin Pecknold and company pouring their souls out over an exquisite arrangement of Sommer’s song “Jennifer” that he performed at Woodstock in 1969.

Bon Iver for Tim Hardin

If we’re going to go with an slightly unknowable, iconoclastic singer-songwriter for this spot, there’s no more natural fit here than Bon Iver.

Virgil Abloh for Ravi Shankar

Instead of trying to come up with a musical entity analogous to Ravi Shankar, it might be more effective to think about his place in the musical firmament in the 1960s. Shankar rubbed elbows with some of the biggest names that decade, but most notably The Beatles. If you’re thinking about who lives in that same stratosphere in 2019, the most logical answer is the guy who carved his own lane and shaped the culture, while also maintaining close ties to megastars like Kanye West, Travis Scott and Drake. It has to be fashion entrepreneur Virgil Abloh -- who is also an in-demand DJ, particularly for festivals and high-profile events. 

Clairo for Melanie

Much like Clairo is in 2019, Melanie was a pop singer-songwriter on the rise in 1969. While Clairo already had her breakthrough moment thanks to the monster success of her single “Pretty Girl,” you can feel there might be another step she’s ready to take in her career, like Melanie did after playing Woodstock, when her breakthrough hit “Lay Down (Candles In The Rain)” hit No. 6 on the Billboard Hot 100.

Jaden Smith for Arlo Guthrie

One is the delightfully off-kilter progeny of an era-defining musical talent and cultural figure. The other is also the delightfully off-kilter progeny of an era-defining musical talent and cultural figure. What’s more, Jaden Smith is one of the premier free-spirits of the Gen-Z era, a perfect modern analog for the hippie movement that birthed Arlo and so many others a half-century earlier. 

Kacey Musgraves for Joan Baez

If you’re looking for a generationally talented, roots-based artist with a pen as incisive as her voice is lithe, who is also totally unafraid to speak truth to power when the occasion calls for it -- and who doesn’t have a ton of crossover hits, but still remains known and respected by all -- you’d be hard-pressed to find a more compelling candidate than country star Kacey Musgraves.

Black Midi for Quill

Not too many people were familiar with Boston rockers Quill before they hit the Woodstock stage around noon on the second day of the festival. They were a shot in the dark, hoping to make an impression on the early-rising field of several hundred thousand hippies. Black Midi, who sound nothing like Quill, are also an off-kilter, progressive band on the rise who you could easily see making the most of a noontime festival set.

Father John Misty for Country Joe McDonald

This spot demands and enigmatic frontman with an alter-ego who inspires a deep and abiding love from his vociferous fanbase, as well as a gift for crafting wiseass, cultural commentaries that speak with sardonic wisdom about the ills of our society writ large. Father John Misty fits that role to a T. You also have to consider that Country Joe played two different sets at Woodstock, one solo, and one with his full band Country Joe & The Fish. You can easily see Misty handling double-duty here no problem, busting out an acoustic guitar to play “Leaving LA” and “I Went To The Store One Day” one night and returning again the next to hit the crowd with noisy renditions of “The Ideal Husband” and “I Love You Honeybear” with help from his full band.

Flying Lotus for Santana

You need someone who’s really going to make an impression in this spot. Carlos Santana famously played Woodstock while tripping out of his mind on mescaline. Some say that’s what fueled he and his band to such mind-expanding heights on “Evil Ways” and “Soul Sacrifice.” Flying Lotus certainly has the potential to conjure up the same kind of magic with his signature array of psychedelic compositions, especially if his collaborator and friend, the bassist Thundercat comes along for the ride.

Jason Isbell for John Sebastian

John Sebastian was a master at marrying a wide variety of different musical elements like country, blues, folk, and American together much in the same way that Jason Isbell has managed to do in recent years on albums like Southeastern and The Nashville Sound. Like Sebastian, he's also able to pare down his music from the filled-out, fully realized studio recordings, to something that sounds more stripped-down and intimate like the former was forced to do with hardly any notice at Woodstock. They both also began their careers in successful bands first before stepping out into the spotlight on their own: Isbell in the Southern rock group Drive-By Truckers, and John Sebastian in The Lovin’ Spoonful.

Anderson .Paak & The Free Nationals for Keef Hartley Band

Keef Hartley was a drummer first, and anyone who has seen .Paak live knows that the show really kicks things up a notch when the singer/MC takes his turn behind the kit.

St. Vincent for The Incredible String Band

You don’t hear much about the Incredible String Band these days, but in their time, they were a critically acclaimed psych-folk band only too willing to push the envelope into innovative new realms. While St. Vincent’s oeuvre sounds almost nothing like them, she shares a willingness to experiment; testing out different and sometimes jarring sonic elements in an attempt to break new ground. They also both have a penchant for theatrical live performance.

Portugal. The Man for Canned Heat

They literally named their last album Woodstock, how could they possibly be excluded from this festival? In this scenario, “Feel It Still” is used the same way as “Going Up the Country” during a pre-festival montage scene in the inevitable documentary feature.

Twin Peaks for Mountain

The Leslie West-fronted band Mountain were a welcome injection of brashness and heaviness onto the Woodstock stage, in their third-ever concert as a band. Much in the same way, young Chicago rockers Twin Peaks could give these hypothetical festivities an irreverent kick in the ass it would so richly need.

?Vampire Weekend? for The Grateful Dead

Vampire Weekend have drawn quite a few comparisons to the Grateful Dead from several corners following the release of their most recent album Father of the Bride. Depending on which era of the Dead we’re talking here, the amount of stock you take in those comparisons may vary. That being said, they’ve definitely embraced one critical facet of their forerunner’s career over the last year by exploding out their compact pop songs to their outer limits with lengthy jams while onstage. They also have a propensity of mixing up the setlist from show to show, keeping both diehards and casual observers on their toes in classic Deadhead fashion.

Ariana Grande for Creedence Clearwater Revival

This comparison might seem jarring, until you consider where both of these artists where around this point in their careers. Creedence Clearwater Revival were arguably the most impactful band in America when they played Woodstock after releasing two critically beloved and commercially successful albums in the previous year, Bayou Country and Green River. The same could be said for Grande, who already headlined Coachella and Lollapalooza on the backs of her zeitgeist-shifting projects Sweetener and Thank U, Next. All she needs to do next is drop her version of Willy and the Poor Boys and it’s a wrap.

Miley Cyrus for Janis Joplin

This slot really calls for a powerhouse vocalist who has the ability to adapt to whatever climate she’s thrown into. Miley Cyrus has proven her chops in that arena time and time again, whether through many of her own pop Bangerz, the classic country duet with her Godmother Dolly Parton on “Jolene,” or while honoring Chris Cornell with her visceral take on Temple of the Dog at the singer’s recent tribute show. Imagine what she could even do taking on some of Joplin’s signature tunes like “Ball and Chain” or “Piece of My Heart.” She also perfectly inhabits the free-love, happy hippie, won’t-take-anyone’s shit aesthetic, making her a more than worthy successor to Janis.

Janelle Monáe for Sly and the Family Stone

For a brief moment in time, around 4:00 in the morning on the second night of Woodstock, Sly and the Family Stone turned Max Yasgur’s Farm into one of the most joyous, high-energy dance parties on planet Earth. While there are several artists out there today who could probably pull that off, practically no one can match Sly and Co. in terms of exuberant intensity, joyful funk vibes or clear-eyed political consciousness as well as Janelle Monáe. Getting people up and out of their sleeping bags right before the crack of dawn is a massively tall order, but with songs like “Dance Apocalyptic,” “Q.U.E.E.N.” and “Screwed” in her arsenal, if anyone can do it, it’s her.

Travis Scott for The Who

The Who were, in the parlance of Travis Scott, the original Ragers. They were the loud – very, very loud – theatrical quartet who were more than willing to get physical onstage, frequently smashing their own gear to smithereens, while provoking their fans to go truly nuts out in the audience. Scott has consistently made the same mark during his own live performances, inspiring his legion of diehards to go as hard as he does when he hits the stage, like the guy who jumped from an actual balcony during one of his shows. He’s the exact kind of artist who can kick things up a notch the same way the Who did all those years ago. In this scenario, Bret Stephens or somebody can play the modern day Abbie Hoffman, until he gets the boot from La Flame. 

Tame Impala for Jefferson Airplane

Jefferson Airplane served as the signature psychedelic pop band to play Woodstock, and there’s no better analogy to them today than Tame Impala: both bands meet perfectly at the place where mind-expanding lyrics meet eye-opening musical arrangements. Also, just think about the prospect of waking up around 8:00 am to the sounds of “Let It Happen.” Pretty incredible.

Chris Stapleton for Joe Cocker

From one husky-throated crooner to another, this just makes way too much sense. Also, why hasn’t Stapleton covered “She Came in Through The Bathroom Window” yet?

J.I.D. for Ten Years After

Not an obvious comparison, but Ten Years After were relative up-and-comers when they arrived at Woodstock, burgeoning with talent, and ready to take the rock world by storm backed by the transcendent talent of their young guitar slinger Alvin Lee. If today’s lyrically adept rappers are the equivalent to yesterday’s guitar heroes, ascendant Dreamville rapper and J. Cole disciple J.I.D. fits this mold quite well. His razor-sharp freestyle abilities make him the perfect analog to fill in the space where Lee once ripped off smoldering guitar solos.

Arcade Fire for The Band

Arcade Fire might not sound much like The Band, but their Canadian/American amalgamized make-up makes them the perfect stand-in for Bob Dylan’s one-time backing band. Both groups also have a knack for crafting precisely-constructed, sweeping anthems that manage to speak to personal experience and the world at large all at once. The yearning desire for freedom at the heart of The Band’s iconic track “I Shall Be Released” for instance feels very in tune with the feelings that permeate AF’s entire The Suburbs album.

Machine Gun Kelly for Johnny Winter

You need a brash, buzz-inducing Texan with blond hair to perform the modern era’s take on the mournfully, ravaged blues that Johnny Winter made his bread and butter. There’s no more obvious candidate than this Houston-born MC.

Migos for Blood, Sweat & Tears

Blood, Sweat & Tears were a band known for reaching across all spectrums of the musical landscape in order to create pop hits while dominating the charts. Migos pulls that trick off nearly better than anyone else, branching out from the main mothership while collaborating with the biggest names in music. Just like Blood, Sweat & Tears brought the hits during their time at Woodstock around 1:00 am, Migos could easily keep the party going for hours on end with songs like “Bad And Boujee,” “T-Shirt,” and “Motorsport.” (The groups also share a habit of naming their albums in numerical order, but that’s really neither here nor there.)

?Boygenius for Crosby, Stills, Nash & Young

Did you know that Woodstock was just the second time ever that Crosby, Stills, Nash & Young played publicly? All four figures had established themselves in their own right, but in 1969 they were still a fledgling collection of four different talents, pulling the best out of one another. Boygenius is close to same place in 2019. The supergroup -- which debuted in 2018 and counts acclaimed solo singer-songwriters Julien Baker, Phoebe Bridgers and Lucy Dacus as members -- have made a name for themselves as a trio through the same combination of stunning songwriting and superb vocal harmonization that made CSN the breakout stars of Woodstock. Add, say, Aussie rocker Courtney Barnett into the Neil Young role here, and you’ve got a recipe for late-night magic.

Jack White for Paul Butterfield Blues Band

The reliable, veteran presence whose music harkens back to an earlier, allegedly more authentic time and place.

Greta Van Fleet for Sha Na Ana

For those who don’t know, Sha Na Na were the only real anachronism booked to appear at the original Woodstock. They were a doo-wop throwback to the earlier sounds of the 1950s, replete with leather jackets and swooping, ducktail hair-dos. There’s frankly no better analogy to them in 2019 than Led Zeppelin look and soundalikes Greta Van Fleet, who have carved out a lucrative niche for themselves on streaming, radio and the live circuit by crafting music that adheres very closely to the bygone aesthetic of ‘70s hard rock.

Kendrick Lamar for Jimi Hendrix

In 1969, Jimi Hendrix was already a cultural monolith with an unassailable catalog of music to his name. He was a widely heralded technical wizard with mind-blowing chops, while also remaining a quiet, but cool presence who changed the vibration of any room he inhabited. No one in 2019 fits that bill better than Kendrick Lamar. Much in the same way that Hendrix was regarded as the greatest guitarist on the planet while he was still around, Lamar is widely assumed to be the prime lyricist of his era, with albums like good kid, m.A.A.d. city, To Pimp a Butterfly and the Pulitzer Prize-winning DAMN. to show for it. He’s also a finely tuned live performer, who has as good a chance as anyone on this list to creating a moment that speaks to the times as effectively as Hendrix did with his now-iconic rendition of the “Star-Spangled Banner.”