20. Gang Starr
Ex Girl to Next Girl (1992)

Hip-hop isn’t big on romantic heartbreak, but this is a particularly fine example. There’s a lot of bragging from Guru about how he’s so inundated with offers since his ex packed him in that she’s probably jealous. But somehow, you get the sense he’s protesting too much: “Went home to see my mom and I saw you at the bus stop – must I stop? I think not.”

19. The Mellows
Smoke from Your Cigarette (1955)

Doo-wop tended to deal in teenage emotions, but there’s something very grownup about this gorgeous forgotten single, a favourite of the late Lou Reed. Lillian Leach’s vocal is limpid and beautiful, the tune sophisticated, the mood of resigned small-hours heartbreak all-enveloping. A miniature masterpiece.