Entertainment (noun): The act of entertaining; the art or field of entertaining; something that amuses or pleases; the pleasure afforded by being entertained; amusement.

A few years ago, a couple of friends and I decided to have a competition. The challenge we set each other was simple: find the saddest song you can. The results were terrifying.

One friend went down the contemporary route. His offerings included Radiohead’s ‘Exit Music (For a Film)’, Michael Andrews’ and Gary Jules’ sublime cover of Tears for Fears’ ‘Mad World’ (a surprise Christmas number one in 2003), Beck’s ‘Lost Cause’ and, my favourite, ‘My Mom’ by Chocolate Genius. ‘My Mom’ is a truly great sad song. It tells the story of the eponymous mother’s battle with Alzheimer’s (If you don’t well up at the line “My mom, my sweet mom, she don’t remember my name” then you’re not human) and even throws in that sad song staple – a dead dog – for good measure. So far, so melancholy.

The best sad songs are the ones that blindside you. 'In the Wee Small Hours’ is, on paper, just another Sinatra/Riddle collaboration – that is until you hear that opening track. It’s that line – “In the wee small hours of the morning/That’s the time you miss her most of all” – that gets me every time. Another sneaky one is ‘Puff the Magic Dragon’ by Peter Paul and Mary. The story of Puff and Jackie is magical – all pirate ships, kings and fancy stuff. And then, BANG! Those last two verses. Heartbreaking? Oh yes.

"A dragon lives forever but not so little boys
Painted wings and giant rings make way for other toys.
One grey night it happened, Jackie Paper came no more
And Puff that mighty dragon, he ceased his fearless roar."

"His head was bent in sorrow, green scales fell like rain,
Puff no longer went to play along the cherry lane.
Without his life-long friend, Puff could not be brave,
So Puff that mighty dragon sadly slipped into his cave."

I’m thirty-six years old and I still get teary when I hear Puff. I’ll never forgive Jackie Paper for abandoning him…

Some of the best heartbreakers come, you won’t be surprised to hear, from the world of country. Some of the titles speak volumes: ‘Cleopatra (Queen of Denial)’, ‘Little Box of Pine’, ‘She’s Acting Single (I’m Drinking Doubles)’. I have a couple of personal favourites. Dolly Parton’s ‘Letter to Heaven’ is a masterpiece of the genre. It tells the story of a young girl whose parents have died, and the young girl asks her grandfather to help her write a letter to her mother and father in heaven. Between the child and her grandfather, they compose a letter positively dripping in sentimentality but the tears only really come at the end – when the little girl goes to post the “letter to heaven,” she is run over and killed by a truck (really!), thus enabling her to deliver the letter in person!

My other favourite is George Jones’ ‘He Stopped Loving Her Today’. This is a song that you really have to hear for yourself (it’s actually a really great song). It tells the story of a man who is besotted with a woman, and describes the day he stopped loving her:

"He stopped loving her today,
They placed a wreath upon his door,
And soon they’ll carry him away,
He stopped loving her today."

The lyrics, the music and Jones’ incredible vocal combine to make this a real heartbreaker – but a classic country song at the same time.

Ultimately, when we got together to choose the winning song, we ended up with a tie. In joint first place we had Red Sovine’s ‘Teddy Bear’ and ‘Gloomy Sunday’ (“the Hungarian suicide song”). ‘Teddy Bear’ is hardcore misery. It tells the story of a young boy who uses his dead father’s CB to chat with truckers. The little boy’s “handle” is Teddy Bear, and he goes on to tell one trucker his story:

"Now, I'm not supposed to bother you fellas out there,
Mom says you're busy and for me to stay off the air.
But, you see, I get lonely and it helps to talk
'Cause that's about all I can do. I'm crippled and I can't walk."
"This was my dad's radio," the little boy said,
"But I guess it's mine and Mom's now 'cause my daddy's dead.
Dad had a wreck about a month ago.
He was trying to get home in a blinding snow.
Mom has to work now to make ends meet
And I'm not much help with my two crippled feet."

Just when you think it can’t get any worse, “Teddy Bear” goes on to tell how he hears his mother crying at night and how he would dearly love to ride in a truck again – just like he used to with his father. Needless to say, the trucker is deeply moved by this and agrees to give Teddy Bear a ride, but when he arrives at Teddy Bear’s home, “Eighteen-wheelers were lined up for three city blocks.” It seems that the entire trucking fraternity, having heard Teddy Bear’s sad story turned up at his home to give him a ride. I’m sniffling just typing this.

The other winner was ‘Gloomy Sunday’. ‘Gloomy Sunday’ was initially a Hungarian song called, cheerily, ‘The End of the World’. It was first recorded in English by Hal Kemp in 1936. Since then it has been covered by many artists, including Bjork, Paul Robeson, Julie London and Billie Holliday. It truly is one of the bleakest songs ever written. The music is absolutely despairing, but it’s the lyrics that nail it for me. Take the opening few lines, for instance:

"Sunday is gloomy, my hours are slumberless
Dearest the shadows I live with are numberless
Little white flowers will never awaken you
Not where the black coach of sorrow has taken you
Angels have no thought of ever returning you
Would they be angry if I thought of joining you?"

This is potent stuff. According to legend, the song has been connected with an unusually high number of suicides and has been banned by several radio stations (these assertions are difficult to prove, but easy to understand).
Heartbreakers will, it seems, continue to flourish as long as people make music. Personally, when I’m in a dark mood, it’s generally songs from the gloomier end of the spectrum that I gravitate towards. Maybe I like them, or maybe it’s because these moods generally come about because I’m drunk and maudlin. It is, however, a curious phenomenon that we seem to derive a masochistic pleasure from exposing ourselves to emotionally negative stimuli.

The primary purpose of pop music is to entertain. Quite where the heartbreaker fits into the definition of entertainment is beyond me, but as a genre, it sure is popular. Maybe we all have a little Gilbert O’Sullivan in us after all…

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