Glastonbury trailblazers: the acts who gave Worthy Farm some of its most memorable firsts

With Billie Eilish set to become the youngest-ever performer to take to Worthy Farm, we look at the groundbreaking stars who keep the festival fresh

An earlier version of this article was published in 2018

Glastonbury 2022 is just around the corner and it’s likely to bring with it new additions to the festival’s rich history of iconic moments. Ever since its inception in 1970, the Worthy Farm bash has been host to performances and events that are now considered legendary and given a home to trailblazers in many different ways.

The first band to headline on one album

The Smiths

When The Smiths headlined in 1984, their self-titled debut album had only been out for six months. Despite that, they only played three tracks from the record (‘Hand In Glove’, ‘Still Ill’, and ‘This Charming Man’), filling the rest of the set with the likes of ‘Girl Afraid’ and ‘Heaven Knows I’m Miserable Now’.

The first dance act to headline

The Prodigy

In the mid-’90s, rave culture was thriving and, with Glastonbury as a reflection of young people’s tastes, it made sense for 1997 to see the first dance act close out events on the Pyramid Stage. Who better to book for that honour than The Prodigy, a trio who had emerged from the underground scene and risen through the ranks, and already had two banging records out with a third – the ‘Firestarter’-featuring ‘Fat Of The Land’ – on the way.

The first rapper to headline


In 2008, controversy was sparked, fuelled, and set ablaze by the announcement of Jay-Z as one of the year’s headliners. He was entering unchartered ground – no other rapper had ever topped the bill at Glastonbury before and people were more than a little divided about the booking. That only seemed to spur him on to put on an incendiary performance, starting with a cover of Oasis‘ ‘Wonderwall’ (a dig at Noel Gallagher, who called having hip-hop at the festival “wrong”) and a setlist packed with knock-out hits.


The first band to cancel

The Kinks

It took precisely one edition of the festival for a band – and headliner – to pull out. The Kinks were due to take on those duties in 1970 but cancelled after seeing the event labelled a “mini-festival”. Why that bothered them so much, we’re not sure but it seems at least one of them isn’t so opposed to Glastonbury anymore – Ray Davies has performed solo a handful of times.

The first headliner

T Rex

With The Kinks no longer up for the gig, Michael Eavis drafted in T. Rex instead. They played for just 1500 people – an idea that seems incredibly quaint now – and gave what Eavis has called one of the most memorable sets at the festival and “the ultimate rock’n’roll gig.”

The first artist to headline twice

Elvis Costello

People complain now about festival bookers running out of headliners and always getting the same old acts back but imagine the furore if any of the big staples of festy headline sets was booked twice in a row. That’s what happened when Elvis Costello became the first artist to headline Glastonbury twice, performing once in 1987 and then being re-invited back for the next edition in 1989.

The first solo woman to headline

Suzanne Vega

Unlike some festivals, Glastonbury has always been quite good at booking a diverse line-up, even when there wasn’t the threat of being taken to task on social media. In 1989, Suzanne Vega became the first solo woman to headline and, we’d imagine, the first headliner to perform while wearing a bulletproof vest. The musician and her bassist Mike Visceglia had received death threats beforehand, prompting police to advise them not to play.


The first metal band to headline


Jay-Z isn’t the only Glastonbury headliner to provoke a less than impressed reaction. In 2014, Metallica found themselves in the eye of a storm about whether metal should be included in the festival’s oeuvre. Others were unhappy with the booking due to James Hetfield’s associations with bear hunting, which some felt went against Glastonbury’s values. A petition was launched but, like most online appeals, had no effect and the show went ahead.

The first grime artist – and first Black British solo artist – to top the bill

Stormzy might have been the first grime artist and the first Black British solo artist to headline the Pyramid Stage, but he didn’t use the platform to keep the focus solely on himself. Instead, his history-making set saw him collaborate with the Ballet Black dance group and bring fellow MCs Dave and Fredo out on stage with him, while he also spoke out about issues that matter. He wore a stab-proof vest daubed with the Union Jack, highlighting inequality in Britain, showed crime statistics on the festival’s big screens and sampled a speech by Labour MP David Lammy on the disproportionate injustice young Black people face in the UK justice system. It all added up to an heroic, historical moment in the festival’s history.

The youngest ever headliner

Billie Eilish
Billie Eilish CREDIT: Samir Hussein/Getty Images for Live Nation UK

At just 20 years old, Billie Eilish is to become the festival’s youngest ever headliner. She’ll close the Friday night on the Pyramid Stage this week, leaving Paul McCartney to become the oldest-ever Glastonbury headliner on the Saturday. Which just goes to show that the Pilton party is a truly cross-generational affair, breaking new ground all the way.