POP MUSIC by Neil McCormick

In the Wee Small Hours by Frank Sinatra (1955)
The great crooner’s turbulent, short-lived second marriage to Ava Gardner resulted in this moody, melancholic masterpiece. Sinatra offers the perversely heroic sound of a man trying to tough out an unbearable loss, from the hopelessly longing title track, the brooding What Is This Thing Called Love to the unconvincing denial of I Get Along Without You Very Well. This is what heartache sounds like.

Blue by Joni Mitchell (1971)
“I am on a lonely road and I am travelling,” announces the dazzling Canadian singer-songwriter on the opening track of her absolute masterpiece, a probing, philosophical, minutely detailed examination of the tension between the urge for freedom and the comforting restrictions of loving relationships. Joni chooses freedom, leaving heartbreak and sorrow in her wake, much of it hers. “I made my baby cry,” she confesses on the magical River.

Grievous Angel by Gram Parsons (1974)
There are not many sounds sweeter and sadder than a doomed Gram Parsons and a young Emmylou Harris singing in tight, tender harmony on Love Hurts. Released four months after his death from a drug overdose, Parsons’s gorgeous final album is a bittersweet country rock landmark about the price of love.

21 by Adele (2011)
“Turn my sorrow into treasured gold” could be the British singer’s motto, a line roared with defiance on Rolling in the Deep. Adele Adkins has made a world-conquering career out of relationship problems. Her second album is the motherlode, in which that giant voice runs the gamut of heartbroken emotions on songs of anger, regret, loneliness, despair, self-healing and forgiveness. Get a full box of tissues ready for the vocal fireworks of the closing track, Someone Like You. “Sometimes it lasts in love, but sometimes it hurts instead.”