Who was the first rapper to headline Glastonbury Festival?

30 June 2024, 11:00

Jay-Z performs on the Pyramid Stage during Glastonbury 2008
Jay-Z performs on the Pyramid Stage during Glastonbury 2008. Picture: Alamy

Radio X takes a look back at the history of black headliners at Glastonbury festival... from Taj Mahal to Jay-Z, right through to Stormzy and SZA.

By Jenny Mensah

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Glastonbury Festival 2019 was a momentous occasion for one performer. Stormzy - whose real name is Michael Ebenazer Kwadjo Omari Owuo Jr - made history by becoming the first black British rapper and solo artist to top the Somerset Festival's famous Pyramid Stage.

2024 will see the festival close with a Pyramid Stage performance from Missouri-born R&B, soul and hip hop star SZA,

But who was the first ever rapper to headline Glastonbury and why was his performance so important?

SZA performs at the United Center in Chicago, February 2023
SZA performs at the United Center in Chicago, February 2023. Picture: Armando L. Sanchez/Chicago Tribune/TNS/Alamy Live News

Who was the first rapper to headline Glastonbury Festival?

Back in 2008, Glastonbury organisers shocked music fans and festival-goers when they announced Jay-Z would be headlining the Saturday night of the festival.

Sandwiched in-between Kings of Leon on the Friday night of the festival and The Verve on the Sunday night, the American rapper stuck out on the main stage line-up that year, which largely housed rock and guitar-based bands.

Jay-Z at Glastonbury 2008.
Jay-Z at Glastonbury 2008. Picture: Alamy

What was the reaction to the news?

In 2008 Jay-Z, who's real name is Shawn Corey Carter, was at the top of his game.

He had already released 10 studio albums, had collaborated with everyone from Mariah Carey to Linkin' Park, and he was widely considered one of the best rappers of all time.

Plus, he was one half of the most powerful music couple in America - married to none other than Beyonce Knowles, who would go on to headline the festival in 2011.

But the fact that rap (and US rap at that) was about to take centre stage at a largely alternative music festival wasn't lost on music critics and fans alike.

The overall reaction was one of shock and confusion, and - while not everyone was totally against the idea - some voices were louder than others...

Enter Noel Gallagher: The most opinionated rock star on the planet. The Oasis guitarist and songwriter had something to say about Jay-Z headlining the famous festival... and as you can imagine it wasn't good.

Noel Gallagher
Noel Gallagher. Picture: Mitch Ikeda/Press

As reported by the likes of The Independent at the time, when hearing that the American rapper would headline the festival in 2008, Gallagher famously told BBC News "Glastonbury has a tradition of guitar music and even when they throw the odd curve ball in on a Sunday night you go 'Kylie Minogue?’ I don't know about it.

"But I'm not having hip-hop at Glastonbury. It's wrong."

"If it ain't broke, don't fix it," Gallagher said of the festival's formula and his predications for its success in the future. "If you start to break it then people aren't going to go. I'm sorry, but Jay-Z? No chance."

Gallagher's comments spread across the pond and made its way into rap and hip-hop outlets as well as in the mainstream media.

The entertainment world was primed to see how Jay-Z's performance would go down, with many envisioning light crowds at the Pyramid Stage or Jay-Z even being booed off stage.

But no one was prepared for what actually happened on the night of his performance on Saturday 28 June 2008.

READ MORE: Are these the best Glastonbury headliners of all time?

Jay-Z's staging takes a pot shot at Noel Gallagher, before the rapper's headline set at Glastonbury 2008
Jay-Z's staging takes a pot shot at Noel Gallagher, before the rapper's headline set at Glastonbury 2008. Picture: Alamy

What happened during Jay-Z's performance?

After much hype and speculation, Jay-Z began his set by playing out Gallagher's comments, and the famous riff to Wonderwall.

The Brooklyn rapper then appeared holding a guitar and singing the Britpop anthem to an ecstatic Glasto crowd.

After singing the famous 1995 track, the audience erupted into cheers and began to chant his name before he launched into his famous 99 problems single.

Jay-Z - Wonderwall/99 Problems (Glastonbury 2008)

Jay-Z went on to play a 29-song-set, which included the likes of Dirt off Your Shoulder, Hard Knock Life, Girls, Girls, Girls, Big Pimpin' and ended with his Linkin Park collab Encore.

Ever the crowd pleaser, Jay-Z's energetic set also made nods to some of the popular artists at the time, such as Amy Winehouse and The Prodigy, as well as acts who he worked with such as Rihanna.

See Jay-Z's Glastonbury 2008 setlist below:

1. Wonderwall (Oasis cover)
2. 99 Problems (AC/DC, Back in Black, instrumental)
3. Is That Yo Bitch (The Prodigy, Firestarter, instrumental)
4. Smack My Bitch Up (The Prodigy cover)
5. Rehab (Amy Winehouse cover)
6. Takeover
7. U Don't Know
8. Say Hello
9. Roc Boys (And the Winner Is ...)
10. I Know
11. A Billi
12. Blue Magic
13. Public Service Announcement
14. Dirt off Your Shoulder (Linkin' Park instrumental)
15. N***a What, N***a Who (Originator 99)
16. Izzo (H.O.V.A.)
17. Can I Get A...
18. Mundian to Bach Ke (Beware of the Boys) (Panjabi MC cover)
19.I Just Wanna Love U (Give It 2 Me)
20. Show Me What You Got
21. Excuse Me Miss
22. Song Cry
23. Girls, Girls, Girls
24. American Boy (Estelle cover)
25. Umbrella (Rihanna cover)
26. Big Pimpin'
27. Hard Knock Life (Ghetto Anthem)
28. Heart of the City (Ain't No Love) (U2, Sunday Bloody Sunday, Instrumental)
29. Encore (Linkin Park instrumental)

Beyonce plays Glastonbury Festival in 2011
Beyonce plays Glastonbury Festival in 2011. Picture: AP Photo/Joel Ryan/Alamy Stock Photo

What was the legacy of Jay-Z's headline performance at Glastonbury 2008?

Jay-Z's set went down as one of the most memorable Glastonbury performances in recent years.

The rapper managed to win the crowd over by paying tribute with one of the most famous songs in British history, while silencing his most vocal and famous critic.

In one fail swoop the New York rapper proved he had not only the wit and the charm to impress British crowds at the Pyramid Stage, but that rappers could pull off memorable and electrifying performances at a traditionally guitar-based festival.

Most importantly, Jay-Z's performance arguably went on to change how we see British festivals today.

His set became the framework for how to play a Glastonbury or festival headline set, and led to more bookings of rap and hip-hop acts at festivals on the whole.

He also paved the way for more mainstream artists to take to the main stage, ushering in headline sets at the festival from his wife Beyonce (2011), Kanye West (2015) and Adele (2016).

And undoubtedly, Stormzy - the first black British rapper to headline Glastonbury - knows he owes a debt of gratitude to Jay-Z, who forever changed our ideas about the kind of artist who could feature on the top slot at the Pyramid Stage.

While he was teasing his own performance last year, Stormzy even shared an Instagram story which paraphrased Gallagher's old quote, thus suggesting he's well aware of who came before him.

Stormzy performs at Glastonbury, June 28, 2019.
Stormzy performs at Glastonbury, June 28, 2019. Picture: Joel C Ryan/Invision/AP/Alamy

Was Jay-Z Glastonbury's first black headliner?

Definitely not. The first black artist to officially headline the Pyramid Stage at Glastonbury was New York blues legend Taj Mahal, who closed the festival on Sunday night in 1981.

And Stormzy wasn't even the first black British artist to top the bill. When the news that the Vossi Bop star was to close the Friday night, he took to Twitter, writing: "I am the first black British artist to headline Glastonbury".

He was quickly corrected by Skunk Anansie singer Skin, who had fronted the band as they topped the Pyramid Stage bill on the Sunday night in 1999.

She posted: "Sorry Stormzy but we beat you to it in 1999! 20 years ago! And while we’re on topic, I was the first black Woman too!"

Skunk Anansie headlining Glastonbury in 1999
Skunk Anansie headlining Glastonbury in 1999. Picture: Alamy

The grime star later apologised saying “no disrespect intended and MASSIVE salute to you!”

But Skin - who was born Deborah Anne Dyer in Brixton, South London - has explained that she was more rattled by another superstar’s claim.

She told The Guardian: “If I’m really honest, I was way more irritated when Beyoncé said she was the first black woman."

The former Destiny's Child star headlined Glastonbury on the final night in 2011.

Skin continued: “I really like Stormzy and I think he does a lot of good. I would never tear that guy down and I would never start a beef and take that moment away from him. But I had to stick up for myself.”

Who's headlined Glastonbury the most times? And other Glasto questions answered!