Re: Top Five Saddest songs

Man, how do you respond to someone who challenges you to a sad song contest and then includes "What a Wonderful World?" What, was "It's a Beautiful Day" taken? Anyway, here's my list of the top five saddest songs:

5) Leonard Cohen - Famous Blue Raincoat - Any list of sad songs needs to include something by Cohen. I had a tough time picking one but eventually settled on this tale of betrayal and sadness in a love triangle. When your friend sleeping with your lover is kind of a good thing because it makes her happier than you were able to make her, you know you're in a sad song.

4) Neil Young - One of These Days - There's just something about Young's singing "One of these days/ I'm going to sit down and write a long letter/ to all of the good friends I've known" that makes me weep like a toddler. Can't we all see ourselves later in life looking back on all the friends we've lost touch with along the way? This song is so great because it's not about dramatics like death and heartbreak. It's about eventuality.

3) Ben Folds Five - Brick - This song gets mad bonus points for combining Christmas and abortion. Yes, despite its sing-a-long chorus this tune tells the (apparently true) tale of Ben Folds' girlfriend having to get an abortion the day after Christmas back in high school. This song doesn't just make you sad, but makes you think confusing thoughts like "what if baby Jesus had been aborted?" Also, Brick was actually the song's second title, his first choice being "On the 13th day of Christmas my true love gave to me: a lifetime of emotional baggage."

2) Antony and the Johnsons - Hope There's Someone - Lead singer Antony Hegarty was gifted with one of the most heartbreaking voices ever bestowed on mankind. So when he starts singing about loneliness and a crippling fear of death, it's not even fair. The song leaves you begging for someone to take care of you in the afterlife, only to have a crushing piano solo shatter your dreams. For other uplifting A&J hits check out "River of Sorrow" about dead children, or "I Fell In Love With a Dead Boy" about... well it's not cheery.

1) The Pogues - Fairytale of New York - Continuing the theme of sadness and Christmas, this is the saddest song of all time. Why? Because the music is so deviously happy. It's one of the best songs ever written, with an incredibly uplifting chorus you can barely hold back from singing along to. Then you remember it's really about a lonely guy in the drunk tank on Christmas eve dreaming of his lost love; their new lives in America destroyed by liquor and drugs. Your body wants to celebrate, but your mind knows it's all a cruel, alcohol-fueled illusion. Merry Christmas.