Top 10 Best Music Festival Headliners Ever

Top 10 Best Music Festival Headliner Acts Ever

Welcome to MsMojo, and today we’re counting down our picks for the top ten most legendary headliners ever to grace the main stage at a music festival.

#10: Dolly Parton at Glastonbury 2014

When Dolly Parton finally performed at Glastonbury 2014 for the legend’s slot on Sunday, it was always going to be a special occasion. Nearly 200,000 people flocked to the Pyramid Stage to hear the iconic songwriter, and to say that Parton delivered would be an understatement. Hits like “Jolene,” “9 to 5,” and “Islands in the Stream” were as well received as can be. Parton, despite being in the business for decades at this point, hadn’t lost a step vocally. When she closed the show with her signature composition “I Will Always Love You,” the crowd could not have been more satisfied. A five-star performance on every level.

#9: The Rolling Stones at Glastonbury 2013

The fact that The Rolling Stones had never headlined Glastonbury was finally remedied when the band hit the Pyramid Stage in 2013. Mick Jagger even jokingly commented on that fact, telling the crowd, “They finally got round to asking us.” You could tell from the opening number onwards that this was going to be a special show. The Stones have no shortage of hits, and highlights from their entire repertoire were on display from the get-go. “Sympathy for the Devil,” “Gimme Shelter,” and many more songs stood out, setting a pace that would not falter over the course of the gig’s two-hour run-time. Over fifty years into their career, and still firing on all cylinders.

#8: Beyoncé at Coachella 2018

Beyoncé was never going to take a headlining spot at Coachella lightly. From the opening seconds of her intro, it was clear that she was planning something truly unique. “Crazy in Love” offered just a taste of the bombast that would follow, and by the time this multi-act show was done, she had brought us a retrospective on her entire career. She even brought out her fellow members of Destiny’s Child for some major nostalgia. Beyoncé was in peak form vocally, and the entire stage show alone was good enough that you could enjoy it with the sound off. A real benchmark for modern-day festival headliners.

#7: James Brown at Woodstock 1999

The hardest-working man in show business didn’t get that title overnight. James Brown was truly an ageless wonder, a man who looked as primed for the stage in his early 20s as he did nearly fifty years later. Brown only accepts the highest standards when it comes to his backing band, and at Woodstock in 1999, their musicianship was on full display. It’s hard to believe that James was pushing 70 at the time of this concert. The career-spanning set never let up in its momentum. By the time all was said and done, the funk and soul legend had well and truly stolen the show!

#6: Bob Dylan at Newport Folk Festival 1965

Is there a more famous and controversial single performance in music history than Bob Dylan’s return to the Newport Folk Festival in 1965? Well, there is so much context and backstory to Dylan’s rejection of the folk scene in the mid-60s that we’d be here all day if we tried to explain it. However, despite his full-band performance being such a polarising moment, the show itself was Dylan at his very best. Sure, a few people in the crowd were upset to see Bob throwing away his acoustic guitar in favor of a new sound, but that new sound could not have been better. Dylan is known to be a somewhat mercurial performer, but on this night, he was in top form.

#5: David Bowie at Glastonbury 2000

David Bowie may have changed styles, genres, and backing bands over the course of his career, but his knack for live performance was a constant. In 2000, he headlined the Pyramid Stage at Glastonbury for a triumphant career-spanning set. Even when vocal struggles threatened to derail him, Bowie never lost his composure. Old classics flowed seamlessly into new releases, and his backing band was as tight as can be. He didn’t skimp on the old material either, giving fans a setlist that offered a taste of every era of his career. All in all, Bowie looked as comfortable on-stage as he ever did!

#4: Prince at Coachella 2008

To say that Prince was an enigma would be putting it lightly. He’s also the type of artist who is unflinchingly confident in his ability to do things his own way and make them work. His Coachella set in 2008 was no different. He didn’t even play a track from his own solo catalogue until eight songs in, adorning the set with covers of artists like Santana, The B-52s, Sarah McLachlan, The Beatles, and one iconic version of Radiohead’s “Creep.” That’s not to say he didn’t play his own hits, though. In many ways, it was the perfect Prince setlist.

#3: Otis Redding at Monterey Pop 1967

Otis Redding was truly hitting his stride at the age of 25 in 1967, performing one of the most powerful sets of the decade at the Monterey Pop festival that year. Over the course of just five songs, Redding showcased a truly enormous amount of explosive energy, pivoting wildly between raw power and gentle honesty. The set contains one of his finest vocal performances, and thankfully, the whole thing was captured beautifully on film. Tragically, this one would be one of the final highlights of his career. Later that year, Redding would die in a plane crash, posthumously hitting number one in the charts with a song he had recorded just three days before, “(Sittin’ On) The Dock Of The Bay.”

#2: Jimi Hendrix at Woodstock 1969

Jimi Hendrix redefined the guitar on several occasions during his short career, but even by standards, Woodstock 1969 was truly special. Hendrix and his band were truly at the peak of their powers. Whatever magical energy that legendary festival was producing… Jimi and the boys were harnessing it during their set. Who knows when Hendrix actually decided to rework the American national anthem on his guitar, but it was a masterstroke. There’s a reason why out of all of the legendary performers who made up this iconic festival, Hendrix’s performance is always the one that springs to mind first.

Before we unveil our top pick, here are a few honorable mentions.

Oasis at Glastonbury 1994

The Brit-Pop Movement at Its Very Best

Daft Punk at Wireless 2007

A Triumphant Display of the French Legends’ Live Capabilities

Amy Winehouse at Glastonbury 2007

The Tragic Legend in Her Absolute Prime

Joan Osborne at Lilith Fair 1997

An Iconic Performance at a Festival Celebrating Women in Music

Lady Gaga with Semi Precious Weapons at Lollapalooza 2010

A Highlight Moment at the Peak of Gaga’s Emergence

#1: Nirvana at Reading Festival 1992

Few bands, if any, could make a giant stage feel like an intimate gig quite like Nirvana did at Reading in 1992. Somehow, Kurt Cobain and his band invited thousands of attendees into a set that felt like it could’ve been played in some dingy grunge club all the way back in Seattle. They were very clearly enjoying themselves too, keeping a light-hearted tone throughout while performing with near-perfect precision. The chaotic nature of the band’s style didn’t get in the way of this being an excellent display of musicianship. It was instantly regarded as one of the best headlining performances of the year, and its stock has only grown in the time since.

What legendary festival performance sticks out in your memory? Be sure to let us know in the comments below.