10 Best Sad Guitar Song

When George Harrison sang "While  My Guitar Gently Weeps," he forever sealed the deal that the 10 best sad guitar songs would be an ever-evolving rock and roll category for as long as people strummed six-strings. Pianos can sound sad, too, but there's just something tragic about a person slumped over a guitar, tears running down the fretboard, that just brings out all the tragedy. There are probably a million sad guitar songs, but let's spotlight 10 of the best.

  1. "The Needle and the Damage Done," by Neil Young. This true story song is about a man Neil Young knew well. He watched the needle take another man, as the lyric goes, which means his friend was a victim of drugs. This is the dark side of the party culture.
  2. "Hurt," by Johnny Cash. Johnny Cash covered this Nine Inch Nails song, and gave it his own touch. Cash was never any great shakes as a guitarist, but this is the fragile Cash giving us slow torture. Don't watch the music video for it, however, unless you fully intend on taking your own life.
  3. "Time Has Told Me," by Nick Drake. Sadly, Drake died young, before most folks could discover his music. He had the sort of voice that made everything sound sad. I can't even imagine what he would do to "Happy Birthday."
  4. "Devonside," by Richard Thompson. Richard Thompson is a storyteller, and this song tells the tale of a woman and man in a doomed, impoverished existence. Thompson has that English voice of authority, and his guitar playing is second to none.
  5. "While My Guitar Gently Weeps," by The Beatles. George Harrison sings it, Eric Clapton plays it, and everyone gets it. Sometimes a musician's instrument can say more than his voice or his words can. And in this case, a weeping guitar does all the talking.
  6. "Comfortably Numb," by Pink Floyd. "Comfortably Numb" is an oxymoron, of course. But Roger Waters is a perpetually depressed singer/songwriter, and he likely felt exactly that way when he wrote it.
  7. "Behind Blue Eyes," by The Who. Pete Townshend wrote a song that could apply to anyone with regrets. And what's sadder than regret? When you look back on what you've done, and wish there was some way to take it all back, it may just make you bawl. Roger Daltry also does an amazing job of bringing Townshend's words to life.
  8. "Runaway Train," by Soul Asylum. This Minnesota band never again reached the heights of this hit song. But what a great song! Life can seem like a runaway train, where one has absolutely no control over circumstances. Come to think of it, it looks like that runaway train ran away with Soul Asylum's career.
  9. "Please, Please, Please Let Me Get What I Want," by The Smiths. Yes, it's redundant to call something a sad Smiths song; all Smiths songs are sad. But this one is sadder than most, as it finds Morrissey begging and pleading to get his way. He won't, of course, which is what makes it so hard to take.
  10. "Tears in Heaven," by Eric Clapton. This song finds the ultimate guitar hero making his guitar gently weep over the personal loss of his son. Just knowing it's a true story makes it almost unbearable to listen to.
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