Boy Better Know had the benefit of darkness headlining the Other in 2017 but I was passing through and it felt like there was nobody there.
Bowie must have been a bit of an unfashionable headliner booking in 2000, and the set he played was much more accessible than would have been anticipated. I doubt he had that big a crowd but with hindsight and given that he stopped touring a few years after, it goes down as one of the great Glastonbury shows.
If I was petty I would go back a few years and ID the folk who thought Elton was only popular enough for a Legends slot. Madness.