David Bowie headlined Glastonbury in 2000 after first appearing at the festival nearly 30 years earlier.
Bowie first played Glastonbury in June 1971, when the event was still the young Glastonbury Fayre. He returned on 25 June 2000 to headline alongside the Chemical Brothers and Travis. The gap was 29 calendar years, commonly described at the time as “30 years” or “almost 30 years,” so David Bowie is the canonical answer to the quiz question.
His 2000 performance became one of the festival’s most celebrated sets. The concert included major songs from across his career, while Bowie wore a distinctive Alexander McQueen coat whose design echoed the hat from his earlier Glastonbury appearance. The performance was later released in full as the live album Glastonbury 2000.
The key mix-up is the date: Bowie’s first appearance was in 1971, not the inaugural 1970 festival. The “30 years earlier” wording is therefore an approximate anniversary description.