Best Of Rock: 10 Of The Saddest Songs

By Ralph Greco, Jr.


There’s no accounting for what’s going to stop us cold and remind us of that long-lost ex, something that slices through our heart. For me, there are plenty of moments in the rock I listen to — lyrics that get caught in my throat when I sing them; guitar leads that make me weep like a baby; songs that I know are going to make me sad with longing but I turn the radio up louder when they come on and give them a spin on the old turntable just to pick at the scab that is my memory. Sometimes, it’s not even a whole song that does it — it might just be a part or a turn-around that makes it a sad song. Below is a top 10, totally unscientific, totally personal (as always) list of the saddest songs in rock and roll.

1) “Romeo And Juliet” (Dire Straits) – The amazing Mark Knopfler is one of the great guitarists to ever pick up the instrument as far as I’m concerned. His gift for creating the most perfect and poignant musical moments has to do with an economy of notes. And it is no more evident than when he plays the three-note echo-laced lead at the end of “Romeo and Juliet,” a wrenching love song from Dire Strait’s 1981 album Making Movies. The fact that the main guitar phrases are played on a Dobro doesn’t hurt either in making this song so unique and plaintive.

2) “Beauty And The Beast” (Stevie Nicks) – Yes, the wonderful Stevie Nicks will always land with “Landslide” and the line: “I’ve been afraid of changing cause I’ve lived my life around you.” For me though, there are just too many startling beautiful moments in her song, “Beauty And The Beast.” This is such a sad, sad song that shutters me to the bone. First of all, how ‘bout the enchanting lady using all forms of the word “to” in the lyrics — “Two children,” “too blind,” “to see.” That alone should garner praise for her amazing songwriting skills. But her whispering “La Bette, La Bette” at the end of the song and the final words, “my beautiful, beautiful, beautiful, beautiful beast” — these are what really bring tears to my eyes.

3) “Can We Still Be Friends” (Todd Rundgren) – Here is a massively sad song from start to finish, but for me the slice-and-dicing of my heart comes after the lilting, “la-la-la’s” that Rundgren sings over the chorus. Ignoring the fact that Rundgren played and sang everything on the Hermit Of Mink Hollow album, “Can We Still Be Friends” is a perfectly sad song on its own. The Robert Palmer cover, pretty much a note-for-note rendering, kicks sad ass too.

4) “Martha” (Tom Waits) – This is basically a piano/vocal tune mining banal lyrical ground, but sometimes it’s the simplicity of things and the fact that they are so common to everyone’s experience that makes them so powerful. “Martha” doesn’t have one specific moment in it that stops me in my tracks because the whole damn song simply destroys me. As Spinal Tap’s NIgel Tufnel once remarked about writing a song in the key of D minor — “it makes people weep instantly” — well…“Martha” makes me weep instantly. From the start of that plinkity, slightly out-of-tune piano, I am a complete goner.’

5) “Shine On You Crazy Diamond” (Pink Floyd) – The four-note guitar opening of this epic is another magical musical moment. Guitarist David Gilmour has always been able to deliver effective guitar phrases succinctly and beautifully. What he manages here not only sets the sad tone for this expansive piece (which takes over two LP sides of 1975’s Wish You Were Here), but also for the entire Pink Floyd album about sadness and longing. Much of that sadness derived from the harrowing downfall of Syd Barrett.

6) “4th Of July, Asbury Park (Sandy)” (Bruce Springsteen) – This one hits me on a personal level because of where I live — not more than an hour from the seaside haunts Bruce Springsteen sings so eloquently about. “4th Of July, Asbury Park (Sandy)” is from The Wild, The Innocent And The East Street Shuffle, and it evokes the boardwalk, the ‘down the shore’ vibe (yards away from what things are like on The Jersey Shore), the smell of creosote. Those suspended single notes that David Sancious plays on electric piano after the Boss sing s, “Sandy…that waitress I was seeing lost her desire for me,” always brings tears to my eyes.

7) “Taxi” (Harry Chapin) – When we lost Harry Chapin to a tragic traffic accident in 1981, we lost one of our greatest pop storytellers. “Taxi” is one of those songs I try desperately to turn away from whenever I hear it, but find I never can. It is the entire song, but especially the line, “She was gonna be an actress and I was gonna learn to fly,” which he repeats throughout the song, has such longing that I am blown away time and again at how well this guy could write.

8) “Ten Years Gone” (Led Zeppelin) – Appearing on the double 1975 album, Physical Graffiti, this is a truly beautiful tune with Robert Plant at his vocal best. My favorite lines? “Did you ever really need somebody/ And really need ’em bad/Did you ever really want somebody/The best love you ever had.” And while I admit a personal connection to these lyrics, really this is one killer song about lost loves and too much time spent away from them.

9) “Bookends” (Simon & Garfunkel) – This one is short and sweet but packs a punch. We all have heard those heart-wrenching lyrics: “Time it was and what a time it was it was/A time of innocence/a time of confidences/Long ago it must be/I have a photograph/Preserve your memories/They’re all that’s left you.” Add Paul Simon’s acoustic as he and Art Garfunkel execute a simple, two-part harmony, and you have what may be the shortest, saddest song ever.

10) “The Last Resort” (The Eagles) – As you can see, they’re not all love songs on this list. “The Last Resort” is an expansive history-like lesson of a tune that ends the Eagle’s Grammy-winning Hotel California, an album replete with amazing tunes. Don Henley once remarked that “The Last Resort” remains one of his favorite songs and it is by far my favorite of all of this band’s songs, as well as being a real heart wrencher.

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