1. ‘Nothing Compares 2 U’ by Sinéad O’Connor
The original version of ‘Nothing Compares 2 U,’ tossed off by Prince in the mid-’80s and released by the purple one's protégés The Family, is a straight-up (and pretty forgettable) break-up song. But the late Sinéad O’Connor’s version dialled the sad factor to 11, channeling the singer’s very real grief from the death of her mother five years previously. A superb vocal performance – the sound of naked sorrow – plus layers of weeping synth strings and an iconic, tear-streaked music video added up to one of the most successful sad songs in musical history. Pop music doesn’t get much closer to the bone, and it's all the more poignant following her death in July 2023. Rest in peace Sinéad.