Jay-Z was the first major hip-hop artist to headline Glastonbury’s Pyramid Stage, doing so at the 2008 festival. His booking became one of the most discussed moments in the festival’s modern history.
Glastonbury had a reputation for guitar-led rock and alternative music, so some commentators questioned whether a rap artist belonged in the headline slot. Oasis guitarist Noel Gallagher publicly criticised the decision. Jay-Z answered the controversy during his performance by opening with a playful cover of Oasis’s “Wonderwall,” turning the debate into part of the show.
The 2008 festival took place from 27 to 29 June, with Jay-Z headlining on the Saturday night. His appearance was ultimately widely viewed as a success and helped demonstrate that the Pyramid Stage could accommodate major artists from hip-hop as well as rock, pop and electronic music. The question asks about the first hip-hop headliner, not the first hip-hop act to perform at Glastonbury: artists including Cypress Hill, De La Soul and The Roots had appeared at the festival earlier.