Year in year out, Glastonbury has proven itself to be the best music festival in the world. You only have to look at the number of people that attend this five-day music marathon, to appreciate just how much it’s loved. With some 210,000 people flocking to soak up the music and the atmosphere, as they do when visiting Seaclose Park at the Isle of Wight Festival, it makes Glastonbury big enough to be a city in its own right.

Of course, for this festival to have stood the test of time, it had to have had some great headliners to keep the crowds entertained. Now in its 50th year, there are some great performers taking to the stage(s) yet again, but who have been the best headliners over the years? Here’s our take.


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Its all about the bookings

Before we get into who the best three headliners are, have you ever stopped to wonder who has the responsibility to book these acts? No doubt you’re aware that Glastonbury is made up of numerous areas, almost like lots of mini festivals within a festival. What you may not have known is that each of these areas has its own organiser who is responsible for the music.

Over at Croissant Neuf, the organiser, for the last 36 years, has been Sally Howell. Speaking to Betway Online Casino, Howell reveals the stresses and strains of getting the music right. Referring to the huge responsibility that it is, she states “By the end of March, we have it all booked and the closer it gets to the festival, my life becomes one big spreadsheet”.

With that said, let’s get onto the three best headliners:

2004, Paul McCartney

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What’s great is that Macca is back at Glastonbury for 2022. The hope would be that having just turned 80, he can match his performance from back in 2004. Having played a full 33 songs, the fact that every member of the crowd knew every word to every single one, is enough to make McCartney one of the best headliners ever (that’s assuming you can ignore the slightly awkward/embarrassing humour that started to creep in!).

2000, David Bowie

It’s the first Glastonbury of a new millennium, and who better to grace the stage than a certain Mr Bowie. Of course. Bowie had been here before and had already wowed crowds at Glastonbury back in 1971 when the festival was still in its infancy. his time headlining in 2000 made us all remember just how many iconic songs he had created. What makes the 2000 performance even more remarkable is the fact that Bowie appeared fresh after a bout of laryngitis.

1995, Pulp

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The thing with this headlining performance in 1995 is the fact that it was never meant to happen. The Stone Roses had been booked to play, but the broken collar bone of John Squire put pay to that. Putting Pulp centre stage was nothing short of a gamble, but it was one that paid off. The six-piece Sheffield-based band put on a performance that was nothing short of outstanding.

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