Hello dear readers. Usually I first write something in Portuguese and then translate, but I noticed I’ve been lacking the focus and energy to do so, and the entries in English hadn’t been coming around. So this time I’m starting with you guys. Be honored, hehehe. Well, I’ve prepared a list of twenty sad songs which I really like. At first I thought about ten, but the list of candidates just kept on growing, so I drew the line at 20. It’s possible you’ve seen similar rankings elsewhere. One thing I tried to do – and I don’t know if that makes my compilation different – was to avoid upbeat melodies with sad lyrics, contemplative songs or slow songs which aren’t really all that sad. Instead, I tried to focus on the ones that really hit hard. If I succeeded, you’ll be crying by the end, hehehe.
20. Foolish Games – Jewel
Released on the album Pieces of You, in 1995.
Heartbreaker : “well in case you failed to notice, in case you failed to see, this is my heart bleeding before you, this is me down on my knees”
Even though it hints a romantic relationship, the essence of this song are the feelings of inferiority and inadequacy. A simple person, interested in simple things, confronted by someone with far more intelectual development, but not enough tenderness and sympathy.
19. Here Today – Paul McCartney
Released on the album Tug of War, in 1982.
Heartbreaker: “and if I say I really loved you and was glad you came along”
John Lennon’s death moved the whole world, and his former band mate and friend Paul McCartney must have been moved quite a lot as well. So much so that he wrote Here Today as a means of ultimately communicating with Lennon in death – something they hadn’t been doing much in life. Ah, what am I doing? It’s a waste of time lecturing anyone about the sadness of Lennon’s death.
18. Best I’ll Ever Be – Sister Hazel
Released on the album Chasing Daylight, in 2003.
Heartbreaker: “I keep thinking that you’ll wake me up with a whisper in my hear, I keep hoping that you’ll sneak in my room”
Ah, reminiscences. Who in this life hasn’t thought that it would be so much better to go back to adolescence, when life was simpler (even if we believed it was awfully complicated)? And, of course, one of the symbols of adolescence is first love. In Best I’ll Ever Be, a grown man, who defines himself as tired, remembers his days with a lover whom he spent time with by the school, and wonders if life will ever be as happy. I wonder that myself sometimes.
17. Why – Annie Lennox
Released on the album Diva, in 1992.
Heartbreaker: “I may be mad, I may be blind, I may be viciously unkind but I can still read what you’re thinking”
Sinking slowly; that’s the idea I get from this song. It’s one of those classic cases of the performer making all the difference. Annie Lennox is perfect while performing Why? And “why” is sometimes the most crucial question one can ask. And one that we don’t have any answers for.
16. Last Kiss – Pearl Jam
Released as a Christmas single for fan clubs in late 1998, and then commercially in 1999.
Heartbreaker: “I held her close, I kissed her – our last kiss – I found the love that I knew I had missed”
The version by J Frank Wilson and the Cavaliers is kind of sad as well, but Pearl Jam makes the whole thing moodier. In this version, the hope of meeting the just dead lover in heaven is less important than the pain of watching her die after a car crash.
15. Nothing like You and I – The Perishers
Released on the album Let There Be Morning, in 2003.
Heartbreaker: “we spent some time together crying, spent some time just trying to let each other go”
Two former lovers meet sometime after splitting up. They can’t go back to when they were together, but they still have feelings for each other. All that’s left to do is cry a little, think of what could have been, comfort each other and prepare to go away again.
14. Ne me quitte pas – Mireille Mathieu
I couldn’t find out when it was originally recorded.
Heartbreaker: again, there isn’t one, it’s a context thing.
A version that’s commonly attributed to Édith Piaf, this is much more powerful than the original version, by Jacques Brel. A woman promises impossible things to her lover, as long as he doesn’t leave her (the translation of the title is “don’t leave me”).
13. Everybody Hurts – R.E.M.
Released on the album Automatic for the People, in 1992.
Heartbreaker: none, really, it’s more of a whole deal.
This was one exception I made to the “contemplative” rule. Everybody Hurts actually brings a message of endurance, tells one not to quit in times of trouble. But it captures the spirit of times of trouble so well that it’s almost impossible not to associate it with sadness. And it is, after all, a beautiful song.
12. Slow Motion – Third Eye Blind
Released on the album Blue, in 1999.
Heartbreaker: “my sister’s eating paint chips again, maybe that’s why she’s insane; I shut the door to her moaning and I shot smack in my veins”
This isn’t about lost loves or the good times left behind. A small time drug dealer just shot someone (who he believes to be the son of his former English teacher). As he waits for the police to come get him, he thinks of his life and those of the people who surround him. All he sees is misery and pain. In the US, the song was originally instrumental, with only the chorus being sang.
11. I’m About to Come Alive – Train
Released on the album My Private Nation, in 2003.
Teenage love leaves great marks, no doubt. But what about adult relationships? When love isn’t the only thing you need to think about, daily life gets pretty hard. This song is about a man overhearing his wife talking to a friend on the phone and noticing just how sad she is. All he wants is for her to hang on a while longer. This song was recorded and released as a single by singer David Nail, who was unable to convey the married-and-worn-out-man sensation brought by Pat Monahan.
Ok, now it’s time to get to the top 10. Are you sad already, hehehe? Take a breath, and let’s go.
10. Long Night – The Corrs
Released on the album Borrowed Heaven, in 2004.
Heartbreaker: “but I’m all, all alone again, thinking you’ll never say that you’ll be home again”
Ok, this one does get a little upbeat at times, but Andrea Corr’s passionate and sentimental vocal performance makes it heartbreaking. One of the greatest symbols of anguish is not being able to fall asleep. What you want most is to lay your head down and stop all thoughts. But if you do go to bed, you just turn around and around until you realize the futility of this exercise: no matter what you want, this is going to be a long night. Been there a couple times myself.
09. The Freshmen – The Verve Pipe
Released on the album I’ve Suffered a Head Injury, in 1992.
Heartbreaker: “stop a baby’s breath and a shoe full of rice”
Rather unknown, at least in Brazil, this song describes, not too directly, the suicide of a former lover and the devastation left behind in her boyfriend and friends. Apparently, the suicide was an exaggeration from the singer and songwriter Brian Vander Ark; what really happened was that his former girlfriend had an abortion, which later caused him to feel guilty. One way or the other, this is one sad song.
08. Perfect Memory – Remy Zero
Released on the album The Golden Hum, in 2001.
Heartbreaker: “as they lowered you down my heart just jaded, in that moment the earth made no sound”
Yeah, death is sad. Number nine on the list attested it, but there’s more to talk about. In Perfect Memory, a man talks about a friend from the past. At first, the feeling of sadness is cryptic. By the end, the singer finally states that he’s talking to a dead friend whose funeral he was present for.
07. Dust in the Wind – Kansas
Released on the album Point of Know Return, in 1977.
Heartbreaker: “I close my eyes only for a moment and the moment’s gone”
Life is ephemeral, and will slip through your fingers at the slightest lapse. That’s the lovely message conveyed by Kansas greatest – and some would say only – hit.
06. All by Myself – Eric Carmen
Released on the album Eric Carmen, in 1975.
Heartbreaker: “I think of all the friends I’ve know, but when I dial the telephone, nobody’s home”
Loneliness as it was best represented. Eric Carmen’s most known song talks of a man who finds himself unable to find friends or companionship. Memories of the past are what he clings to.
05. Nothing Compares 2 U – Sinead O’Connor
Released on the album I Do Not Want What I Haven’t Got, in 1990.
This is an ultimate tearjerker, make no mistake about it. This song wants to make you cry maybe more than any other song ever has. But the fact is it’s good enough to succeed, from the melody to the breathtaking performance by Sinead. It was written by Prince (back when he wasn’t known by a symbol – or should I say “back when he was known”?).
04. Goodbye My Lover – James Blunt
Released on the album Back to Bedlam, in 2004.
Heartbreaker: “I’m so hollow, baby”
If I had to choose just one song to describe how painful it is to see your love vanish, this would be it. It hits me more personally than any other sad song I can think of.
03. Streets of Philadelphia – Bruce Springsteen
Released on the soundtrack album of movie Philadelphia, in 1994.
Heartbreaker: “so receive me brother with your faithless kiss, or will we leave each other alone like this in the streets of Philadelphia”
Streets of Philadelphia combines some of the things I mentioned about other songs on the list: there’s the absence of friends, the lost loves and death – in this case, the fear of it. Written for the movie Philadelphia (starring Tom Hanks and Denzel Washington), the song describes the thoughts of a man with AIDS, back in the days when people still feared they might be infected just by being in the presence of a sick person (if you’re young, believe me, these days have existed). He is sick, alone and despair is setting in.
02. Yesterday – The Beatles
Released on the album Help!, in 1965.
Heartbreaker: “Suddenly, I’m not half the man I used to be, there’s a shadow hanging over me”
And Paul McCartney is the only one to make the list twice. According to the Guinness World Records, Yesterday is the most recorded song in history. And according to my dad, he once caught grandpa whistling it, even though the old man would say he hated The Beatles. Yesterday is beautiful in every sense, and it’s a great example of sadness, even in its simplicity. This is just a guy who longs for lost love. And from just that, a masterpiece was crafted.
Now, if you haven’t loved and lost, you haven’t lived. The song that takes the number one place in this list deals with something that, thank God, very few of us actually know: how a parent feels upon the loss of a child. Eric Clapton eventually dealt with it using what he knows best: he wrote a song. This song became one of his greatest hits, and one that very few people are unfamiliar with. By now I’m pretty sure you know what I’m talking about:
01. Tears in Heaven – Eric Clapton
Released on the soundtrack album of movie Rush, in 1992.
Heartbreaker: what part of this song isn’t a heartbreaker? But I’ll quote “beyond the dark, there’s peace, I’m sure, and I know there’ll be no more tears in Heaven”


