A complete history of the Isle Of Wight Festival in 10 headliners

From Dylan and Hendrix to Jay-Z and Queen, the history of the UK's oldest festival is written in its stars

The Isle Of Wight Festival has been a mainstay of the UK summer for over two decades now, though its origins stem from the countercultural golden age over 50 years ago. The 65,000 capacity event is no longer the hippie garden party of yesteryear however: Seaclose Park now welcomes music’s greatest acts spanning the spectrum from modern greats to innovative up-and-comers.

Isle Of Wight Festival’s promoter John Giddins has a knack of convincing legacy artists to head over to the idyllic island, with Pet Shop Boys, Green Day and The Prodigy all headlining in 2024. It’s a typically heady mix of radio-ready anthems from past and present, which is characteristic of the beloved event, and has been since its revival in 2002. 

For a clearer picture of the festival’s history – and why it remains one of the UK’s premier fixtures of the festival season – let’s look back at the timeline of epic headliners over the years

Bob Dylan, 1969

Bob Dylan - Isle of Wight 1969 B&W footage/HQ audio

Before the concept of festival exclusives became part of the event organiser’s lexicon, in 1969 the Isle of Wight Festival promoters pulled off a major coup by securing Bob Dylan to headline their second edition. An estimated 250,000 people flocked to the island (double the local population, whose travellers included three of The Beatles in John Lennon, George Harrison and Ringo, along with Keith Richards) to witness Dylan’s first performance in three years following the motorcycle crash which led fans to wonder whether or not he’d ever play again. With The Band in tow, Bob gave a handful of tracks their live debuts – including ‘Lay Lady Lay’ – alongside big-hitters ‘It Ain’t Me Babe’ and ‘Like A Rolling Stone’, in what established the festival as the UK’s most attractive. Dylan’s appearance was also fabled as he snubbed countercultural monolith Woodstock (which had been “put on in his own backyard” in an attempt to coax him out from semi-retirement) weeks before in favour of the Isle Of Wight Festival. 

Jimi Hendrix, 1970

jimi hendrix - all along the watchtower - isle of wight

Though the Isle Of Wight Festival may have evolved into a very different beast nowadays, the legacy of Jimi Hendrix’s lauded 1970 headline performance is the event’s lifeblood. Alongside headline sets from The Doors and The Who that year, Hendrix’s trip to the strange island off of England’s south coast was the jewel in the festival’s crown, encouraging approximately 600,000 folks to venture to see him in what remains the UK’s biggest ever festival attendance, surpassing even Woodstock. Showcasing his latest musical iteration in Band Of Gypsys (replacing the Jimi Hendrix Experience), the seminal guitarist shredded through classics in ‘Purple Haze’ and ‘Hey Joe’ alongside newer numbers like ‘Ezy Rider’ and ‘Message To Love’, the latter of which was the title of Murray Lerner’s documentary about the chaotic weekend that unfolded. Due to the unmanageable level of people that descended on the Isle Of Wight that weekend, Parliament restricted open-air events on the island for over 5,000 people for three decades. Still, Jimi Hendrix’s presence permeates each and every edition to date, with his music and legacy influencing the festival’s iconography – a statue of the imitable guitar icon was even erected at the festival’s former Afton Down location. 

David Bowie, 2004

David Bowie - All the Young Dudes (Live at the Isle of Wight)

After 30 plus years of silence and two modest editions which re-established the event at Seaclose Park – where it remains today – the Isle Of Wight Festival returned to the big leagues with music’s chameleonic king, David Bowie, at the summit. Visibly reinvigorated, looking far younger than his 57 years, the Starman dropped by the Isle Of Wight during the A Reality tour, his first in nearly a decade. And what a spectacle it was: eschewing the temptation to cram the set with new material, Bowie cherry-picked songs from numerous eras of his catalogue, throwing in a couple of Iggy Pop covers that he co-produced back in the Berlin days, a Pixies cover, and a rendition of Mott The Hoople’s ‘All The Young Dudes’, a song he wrote which largely convinced people it was his all along. Finishing off aptly with the arm-waving epic ‘Ziggy Stardust’, it would sadly mark Bowie’s final ever tour after he retired just shy of two years later – no wonder it’s remembered with religious reverence.

R.E.M., 2005

R.E.M @ Isle Of Wight 2005 ProShot

In the year when Morrissey was confirmed to headline the Saturday night and dropped out at the last minute, the heat was on for the Sunday night finale at the Isle Of Wight Festival in 2005. Despite Travis’ valiant effort at filling in at the very last minute the night prior, it failed to meet festival-goer’s expectations. R.E.M., however, relished the pressure: lead singer Michael Stipe slinked around the stage with his trademark band of blue face paint, whilst the lights and mirrors behind him bedazzled the audience who danced with similar abandon. Admitting to signing up to play the festival solely because of its illustrious heritage, the alt-rock pioneers were a worthy addition to festival’s greatest performers with an exquisite set. 

The Rolling Stones, 2007

Rolling Stones & Amy Winehouse - Ain't To Proud To Beg (I.O.W. 2007)

With each advancing decade, The Rolling Stones bat away talk of passing their sell-by-dates with on-stage energy levels that make their peers weep with envy. Their immortality might partly be down to the guests they invite to perform with them each night, like some form of youth-sapping ritual. For their 2007 headline set however, the Isle Of Wight Festival was treated to a once-in-a-lifetime duet of ‘Ain’t Too Proud To Beg’ with the late Amy Winehouse which will live as long in the memory as the remainder of their show-stopping headline set. Mick, Keef, Ronnie and Charlie ensured the audience went home grinning like the Cheshire Cat, with a protruding mechanical platform dragging and plonking the entire band into the centre of the crowd during ‘Miss You’, which remained there for the set’s second half. 

The Police, 2008

The Police - Message in a Bottle - Isle of Wight 2008 - Live HD

Against all odds – given their notorious inter-band feuds – The Police briefly settled their grievances for a global tour which included a headline performance at the Isle Of Wight Festival in 2008. Arguably the world’s biggest band when they broke up over 25 years prior, Sting, Andy Summers and Stewart Copeland performed with the same level of tension and youthful exuberance that made them stand out on London’s punk circuit all those years ago. With the exception of an overly saccharine rendition of ‘Every Breath You Take’, which broadcast unnecessary images of impoverished children on the big screens, The Police’s performance was one for the history books. Shame they never buried the hatchet permanently.

Neil Young, 2009

Neil Young - Day In The Life, Isle Of Wight Festival 2009

Despite being one of contemporary music’s most influential figures, a petition to remove Neil Young from the rank of headliner entered the annals of Facebook in 2009, with many attendees that year (probably) confusing him for Neil Diamond. Typically belligerent in the face of public pressure, Young conjured a magic setlist made up from the fragile country numbers, the politicised countercultural rock, and guttural guitar bangers that earned him the title of ‘Godfather of Grunge’. Making a concession to play ‘Heart Of Gold’ for the “alcoholics” in the crowd, Young did predominantly focus on fan favourites, thankfully, including a rousing version of ‘Rockin’ In The Free World’ complete with umpteen extended outros, and a cover of The Beatles’ ‘A Day In The Life’ before leaving the 50,000 festival-goers with a dense smog of feedback that’d ring out into the early hours of Monday morning.

Jay-Z, 2010

Jay-Z brings out Kanye West for Run This Town, Isle of Wight Festival

It’s still hard to believe that hip hop royalty Jay-Z, and his wife Beyoncé, even stepped foot onto the Isle Of Wight’s humble soil – and his headline set needed to be seen to be believed. Pulling out all of the proverbial stops (in what was arguably the finest trio of headline acts since 1970, with The Strokes in their pomp and Sir Paul McCartney also headlining), Hova paid homage to Hendrix with a cover of ‘Purple Haze’, even inciting a festival-wide Illuminati hand gesture despite the clear confusion amongst the Friday night boozehounds. The pièce de résistance, however, was flying Kanye West over in a helicopter for literally just one song, his then-hit ‘Run This Town’, before departing and leaving the Isle Of Wight Festival absolutely flabbergasted. The festival’s promoter John Giddins gushed shortly after: “When Jay-Z was on, I thought an audience couldn’t go more wild – and then Kanye West walked on. It was extraordinary, the way people erupted… I thought the earth was shaking!”

Fleetwood Mac, 2015

Fleetwood Mac - Go Your Own Way live 2015

The rumour mill had tipped Fleetwood Mac for Glastonbury in 2005, but the soft rock shaggers plumped to trek across the Solent in search of sunnier delights than a rain-soaked Worthy Farm. And they got their own way. With a recently returning Christine McVie making up the Rumours-era five-piece again, it was one of the final times the classic line-up played the UK, much to the chagrin of anyone who couldn’t get their mitts on tickets. With wall-to-wall hits – kicking off with ‘The Chain’ and rounding their set off with the ever-positive fist-pumper ‘Don’t Stop’ – Fleetwood Mac’s performance left the festival crowd floating as freely as one of Stevie Nicks’ neck scarfs. 

Queen + Adam Lambert, 2016

Queen + Adam Lambert - Don't Stop Me Now (Live at Isle Of Wight Festival 2016)

“There’s only one Freddie Mercury,” was very much the mantra of the Isle Of Wight Festival populous as dusk settled on the Sunday night at Seaclose Park ahead of Queen’s arrival on stage. That remains to be true, undoubtedly, yet Adam Lambert convinced everyone in attendance that there were buckets of fancy-free and flamboyant fun to have beyond Freddie. Bringing an air of showgirl entertainment to Queen’s songs – which Freddie himself would’ve no doubt loved – Lambert hit the headbanging highs of ‘One Vision’ and ‘Tie Your Mother Down’ as well as offering up emotional heft when required, particularly on ‘Who Wants To Live Forever’. In tribute to Freddie, the late trailblazer of course made an appearance on the big screens during the operatic section of ‘Bohemian Rhapsody’. “You’re all thinking it,” Lambert quipped in regards to being Freddie’s current replacement. But when the songs are that iconic, and the performance that bombastic, you couldn’t begrudge Brian May and Roger Taylor for wanting to continue with Queen long into the future.

The Isle of Wight Festival 2024 takes place between 20-23 June – this year headlined by The Prodigy, Pet Shop Boys and Green Day. Find tickets here

Photo credit: Stuart Mostyn/Redferns