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Best Glastonbury headliners: the greatest Glastonbury performances of all time

When the cows are away, the bands will play

Best Glastonbury headliners: the greatest Glastonbury performances of all time
Tom Wiggins

Nearly 100 bands have headlined Glastonbury since its inception in 1970. And Stormzy, The Killers and The Cure are set to top the bill in 2019. So there's a lot of competition for the best Glastonbury headliner badge.

UPDATED: Stormzy at Glastonbury 2019 was without a doubt one of the best headliners the festival has seen. At just 25 he was the second youngest ever headliner (beaten only by Bowie) and it was fantastic to see Grime get the top slot. We've added him into the Shortlist - now it's up to you to vote for him.

Fortunately, the world’s most famous dairy farm has seen more Radioheads than Ed Sheerans over the years - but which of the Pyramid Stage’s main performances will still be remembered in 2070?

We’ve picked out the headline sets that put bands on the map, defined eras or helped shape the future of the festival.

Who do you think deserves to be king (or queen) of Worthy Farm? Upvote your favourites and tell us if we’ve missed out any classic sets down below.

Best Glastonbury headline performances

Best Glastonbury headline performances

1. Radiohead, 1997

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With their equipment malfunctioning and Thom Yorke on the verge of walking off stage in a sulk, Radiohead guitarist Ed O’Brien has described the band’s 1997 performance as “like a form of hell.”

The frontman remains chippy for the entire set (Thom Yorke? Surely not!) but from the moment he asks for the lights to be turned on before Paranoid Android, things shift into another gear entirely. OK Computer had been released just a couple of weeks earlier, so it’s easy to forget that a lot of these songs weren’t the bonafide classics they are now, but by the end of the set they were well on the way there.

Vote for the Best Radiohead album.

Credit: BBC Music, YouTube

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Best Glastonbury headline performances

2. David Bowie, 2000

£29.99
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At the turn of the millennium David Bowie was experimenting with new-fashioned download releases and a video game soundtrack, but he turned up on Worthy Farm with no intention of messing about.

Despite coming off the back of a bout of laryngitis he casually but charismatically reminded a packed Pyramid Stage just how many bangers he had (and Hallo Spaceboy). The most extravagant thing about the set was his three-quarter length Alexander McQueen coat – a sartorial nod to the hat he’d worn when he headlined in 1971.

Credit: Official Glastonbury YouTube Channel

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Best Glastonbury headline performances

3. Pulp, 1995

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Headliners pulling out of Glastonbury is, er, headline news these days but bands made a real habit of it in the late ‘90s. After John Squire broke his collarbone in a bike crash, Pulp were parachuted in (not literally, Jarvis Cocker wasn’t wearing the right trousers) to take The Stone Roses’ place.

Being far from first choice and having only recently stepped in to support Oasis on their first arena tour, it was quite a gamble for Eavis to book the Sheffield six-piece, but a suitably self-deprecating yet humble performance meant it well and truly paid off for both parties.

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Best Glastonbury headline performances

4. Blur, 2009

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Some bands reform triumphantly, others are Jet. Blur’s reunion performance at Glastonbury very much fits into the first category. The band had headlined 11 years earlier, but it hadn’t exactly been the crowd-pleasing set many had hoped for.

In 2009, however, after all the fighting and the desire to be taken more seriously, this was an inclusive, emotional celebration of what made them one of the biggest bands in the country in the first place. And with the crowd’s own acapella rendition of Tender continuing long after the band had left the stage, it was obvious to everyone on Worthy Farm and beyond that a real Glastonbury moment had just occurred.

Credit: Blur - Live at Glastonbury Festival, Universal

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Long before Glastonbury was commandeered by posh twentysomethings in designer waterproofs and £100 wellies, it was widely accepted that Pilton’s premier festival was for proper hippies.

That’s who made up the unreceptive crowd that greeted Morrissey, Marr and co in 1984. And while it was by no means a set worth recording and releasing on Betamax, it spawned what must’ve been the world’s least threatening stage invasion and helped to alter the course of the festival towards what became known as indie music, eventually turning it into the cultural behemoth it is today.

Credit: The Sound of the Smiths, Warner Music, Warner Music

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Best Glastonbury headline performances

6. Stormzy, 2019

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The first British rapper to headline Glastonbury, Stormzy took the challenge on headfirst and delivered a barnstorming set that took the audience from the south London freestyle rap battles that began his career, all the way up to his current number one, the brilliant Vossi Bop. Even bringing Chris Martin from Coldplay on to stage didn't dampen the spirits of the show. He ended with Big for your Boots - no encore, no need.

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Best Glastonbury headline performances

7. Paul McCartney, 2004

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Unless it’s Pete Best, booking an ex-Beatle to headline your festival is always going to be a big deal. Even Ringo Starr recalling key moments from Thomas the Tank Engine would draw a pretty decent crowd. But when your name’s Paul McCartney and you can play a set full of songs (all 33 of them) that pretty much every single person in the crowd knows the words to, you’re onto a winner, even if the on-stage patter did veer into embarrassing dad/#AccidentalPartridge territory a little too often.

Credit: PaulMccartney.com

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Best Glastonbury headline performances

8. Beyoncé, 2011

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Anything Jay-Z can do, Beyoncé can do... better? The singer’s performance in 2011 marked the point Glastonbury started booking the world’s biggest pop acts to headline, not just geezers with guitars to please Q magazine readers.

And with stage productions getting more and more extravagant, Beyoncé was the perfect choice to kick off the new era. Getting any remaining doubters on side by opening with Crazy in Love and Single Ladies was probably key, but by the time she finished on Halo, you could count any left on the fingers of one hand.

Credit: BBC, YouTube

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Best Glastonbury headline performances

9. Tyrannosaurus Rex, 1970

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50 Years of Glastonbury at Amazon

Tickets for the inaugural festival on Worthy Farm cost just £1 (one 248th of 2019’s price, plus it included all the free milk you could drink) but the line-up wasn’t exactly bursting; the original ads promised The Kinks, Wayne Fontana and “at least six other groups.”

In the end, The Kinks didn’t even make it, but a pre-abbreviation T-Rex did instead. Only around 1500 people saw the performance but Michael Eavis called it “one of the most memorable slots ever”, even if he did have to give Marc Bolan £100 of his milk money for the next five months to pay for it.

Credit: T-Rex Gold, Crimson

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10. Jay-Z, 2008

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Unfortunately it’s impossible to talk about Jay-Z’s 2008 performance without mentioning Noel Gallagher, aka the Britpop Jeremy Clarkson, and his absurd whining about hip-hop not belonging at Glastonbury. It must’ve come as a surprise to The Roots, Slum Village and The Beastie Boys, who all appeared in the ‘90s.

The fact of the matter remains that even Jigga’s unrehearsed cover of Wonderwall at the start of the set was more enjoyable than Oasis’s last lacklustre headline performance in 2004, not to mention his storming renditions of Big Pimpin’ and Hard Knock Life.

Credit: GlastonburyFestival.co.uk

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SOMETHING MISSING FROM OUR SHORTLIST?

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