The Sounds of Heartbreak: My 10 Favorite Sad Songs and Compositions

Although, like most people, I prefer cheerful and upbeat music – say, John Williams’ Raiders’ March, Billy Joel’s Uptown Girl, or The Beatles’ Eight Days a Week, there are periods when all I’ll listen to is melancholic, even bitterly sad songs. Whether this is simply a matter of taste or a reflection of my own psyche is a thorny question; like most things in life it’s neither one nor the other but a combination of the two. In any case, I think that most of us have songs, movie themes or even “serious” classical music pieces that we listen to when life hands us a bad hand of cards – loss of a job, stress, illness, or a love affair gone terribly wrong.

Here, then, are my Top 10 Favorite Sad Songs and Compositions:

1. And So It Goes (Billy Joel): I first heard this bittersweet ode to a doomed love affair – as Billy Joel describes it, “about a relationship you know won’t last” – while watching his HBO concert from Yankee Stadium in 1990. Billy hadn’t performed it in the concert proper – either on the TV special or the live show I had attended several months before – so when I heard the sad piano solo intro and the opening lines (In every heart there is a room/A sanctuary safe and strong/to heal the wounds from lovers past/until a new one comes along…), I was not only surprised, but I actually misted up. As another Joel song title would put it, Don’t Ask Me Why; I wasn’t dating anyone nor would I seriously fall in love with anyone for almost a decade, but I had to bite my lip to keep from crying. Perhaps it was just the melancholic mood of the words and music, or perhaps it was foreshadowing a life-changing event, but And So It Goes never fails to move me, as it brings to mind a certain young woman who I sang this song to when we met one chilly February afternoon several years ago.

2. Since I Don’t Have You (The Skyliners): This song from the doo-wop era, written by Joseph Rock and performed by The Skyliners, is a love-lost song (boy loses girl, falls into despair) featured in the American Graffiti soundtrack. Its lyrics are a bit over the top at times (I don’t have plans and schemes/And I don’t have hopes and dreams), but I can identify with them.

3. Smoke Gets In Your Eyes (The Platters): It’s been over five years since I heard this song with the woman I will always associate this 1950s doo-wop version of Jerome Kern’s song from the Broadway show Roberta; I’d met someone in a Yahoo chat room, and after several months of chatting, she asked me to meet her in person. After four hours on a plane and a 2-hour drive to a small town way out West, I asked her to dance with me in our motel room (after our first kiss, of course), and knowing I probably wouldn’t be able to see her again, I played this song on the CD player she’d brought along. I still remember, over half a decade’s time, how she placed one hand on my waist and held one of my hands while resting her head on my right shoulder as The Platters sang They asked me how I knew/My true love was true… And I will never forget how, after the song ended, she looked into my eyes with a bittersweet smile.

4. Hallelujah (Rufus Wainwright): Oh, can this song make me cry? With lyrics like I’ve seen your flag on the marble arch /Love is not a victory march / It’s a cold and it’s a broken Hallelujah, how can it not?

This song, which underscores the scene in Shrek when the big ogre is thinking he’s lost Princess Fiona, is definitely a big tearjerker. As sung by Rufus Wainwright, it’s one of those rare pieces of music that has everything – a haunting melody, memorable (if downbeat) lyrics, and emotional oomph that, if it catches you off-guard, can knock the wind out of you. (Sadly, after it was featured in Shrek, it was overused as a sad song on TV and movies. I remember it was used in The West Wing as guest star Mark Harmon lay dying on a sidewalk in New York City.)

5. Yesterday (The Beatles): The most covered song in popular music, Paul McCartney and John Lennon’s classic hit is, of course, another love-lost ditty (although one wonders what kind of song it would have been had Paul stuck to “Scrambled Eggs”). It’s a singer-friendly song; a simple AABA structure, easily remembered lyrics (Why she had to go, I don’t know, she wouldn’t say….), and its universality make Yesterday a truly time-tested classic.

6. Symphony No. 6 in B-minor (Pathetique), Op. 74, 1st Movement: When I was taking music appreciation in college, I heard an excerpt from Symphony No. 6’s first movement; we were learning how to identify specific instruments of the orchestra, and when the woodwinds were being presented, several measures from the Adagio, Allegro non troppo were included. I don’t know why – maybe my mind was dwelling on some girl I liked but was afraid to ask out – but when the melancholic “main theme” of the Pathetique’s first movement wafted across the classroom, tears welled in my eyes; I was thankful that the room was dimly lit and that everyone’s attention was focused on the music, or they would have seen a couple of tears running down my cheeks. There’s something wistful and reflective about the first movement, almost foreshadowing Tchaikovsky’s tragic end just nine days after the work’s premiere on October 28, 1893 – officially of cholera, but supposedly the great composer committed suicide to avoid a scandal due to a homosexual affair he’d had with a Russian nobleman’s nephew.

7. You Don’t Know Me (Ray Charles): I actually heard Bette Midler’s cover of this song first, but one of my best friends sent me an MP3 file of the Ray Charles version, and although the Divine Miss M did a nice job with the classic country song by Cindy Walker and Eddy Arnold, Ray did it better. His more straightforward yet bluesy delivery of lines like You give your hand to me/And then you say, “Hello.” And I can hardly speak, / My heart is beating so evoke all the times my shyness (or cowardice, or simple bad timing) put me in the unenviable situation of falling for someone, then watching her go off with someone else.

8. But Not For Me (Harry Connick, Jr.): I first heard this George and Ira Gershwin song from their musical revue “Girl Crazy” as an instrumental selection in the film When Harry Met Sally…; it wasn’t till I bought the WHMS album that I learned both the title and the lyrics, which are performed beautifully by Harry Connick, Jr. with Marc Shaiman on piano. Like You Don’t Know Me,, the song, with such lines as With love to lead the way/I’ve found more clouds are gray/than any Russian play/could guarantee, might as well be every lonely person’s theme song.

9. Goodnight, Saigon (Billy Joel): As a writer, listener, and former singer, I tend to love songs that tell stories, and this touching tribute by Joel to his friends that went to fight in the Vietnam War is both searing and heartbreaking. Its haunting “helicopter rotor” intro segues into a melancholic solo piano melody and a sad opening first verse (We met as soul mates/On Parris Island / We left as inmates / From an asylum / And we were sharp / As sharp as knives / And we were so gung ho / To lay down our lives) and steadily gets more fierce and yet reflective as Joel describes the sights and sounds of battle (We held the coastline / They held the highlands/ And they were sharp / As sharp as knives /They heard the hum of our motors / They counted the rotors / And waited for us to arrive) that lays no blame on either the Vietnamese or the Americans, but pays equally respectful tribute to both sides’ young soldiers.

10. Main Theme from Summer of ’42 (Michel Legrand): Also known (and recorded) as “The Summer Knows,” this gentle yet haunting theme composed for Robert Mulligan’s bittersweet Summer of ’42 never fails to make me mist up. Whether played by a solo piano, a large orchestra, or even as tinny “source music” when Dorothy (Jennifer O’Neill) dances with Hermie (Gary Grimes) on that last, fateful night they share, Legrand’s beautiful composition evokes memories of old friends…and lost loves.

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