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I have a preoccupation with sad songs, especially songs about love and how things never turn out well. Songs about unrequited love, spurned love, impossible love and the likes. Hence in Hornby-esque style, I will list some sad songs that occupy a special place in my heart and have a special meaning to me.

In no particular order of merit (I just can’t choose between them!):

Jimmy Eat World – Last Christmas

I never fail to listen to this song whenever it is Christmas season. I am not Christian and I don’t attend Christmas parties, and hence most Christmas nights (actually all i think) are spent at home alone. I will play this song and think about opportunities lost.

Neil Young – Heart of Gold

There are varying interpretations of this song. Some suggest that it is about the struggle to find expression for one’s desire to do good, while others say that it is about love and how it is hard to find love. The second interpretation resonates more with me.

Nothing beats watching Neil Young performing this song alone live, without a backing band. The earnestness, sense of solitude and emotional intensity is all there, like a open wound with all its vulnerability.

Everclear – Wonderful

This song followed me all the way from secondary school till now. It has danced its way in and out of my CD and MP3 players so many times it is now a permanent fixture in my MP3 player now.

I listen to this song whenever things go wrong at home (especially when my parents fight). The song doesn’t help matters but at least I feel that I have a kindred spirit in Art Alexakis.

What this song stands for is the gradual realisation as we grow older that the past, like scars, cannot be erased. We cannot close our eyes and hope everything will be wonderful again, because it just won’t happen, as much as we like it to happen.

Nirvana – You Know You’re Right

Ok this is not a song about love, but it remains a sad song nevertheless. This song, to me, is the best Nirvana song ever written. The sheer anguish when Cobain screams the single word “pain” into the mic is astounding. And like a knife, it tears and rips through one’s psyche and soul, and I suspect, stands as an omen that Cobain would than take his own life.

Massive Attack – Teardrop

I just love that single line that Elizabeth Frasier drops: love, love is a verb/ love is a doing word. Doesn’t that succinctly sum up the situation that anyone who pines after another? If you love someone, you have to let it show. Otherwise you will never get it.

Fleetwood Mac – Dreams

Stevie Nicks was fantastic in this song. And the song is so meaningful. One of the songs that I will play to myself late in the night, while I think of the past.

Johnny Cash – Hurt

This song is unique because it is one of the few songs that I will think twice before playing it. Such is the power of this song. It depresses me utterly.

Cash conjured up an ocean of emotions with just a simple guitar and voice. This is a song recorded just before he passed away, and he was well aware of his impending passing when he wrote this song’s lyrics: and you could have it all/ my empire of dirt/ I will let you down/ I will make you hurt. The video is even more arresting; we see a Johnny Cash stripped of all makeup and hair, at the brink of death. However lest we lapse into total negativity, this is at once a song about rebirth and life as it is about death: if I could start again/ a million miles away/ I would keep myself/ I would find a way.