12 Best Sad Guitar Songs

Published Categorized as Acoustic Guitar Songs, Songs

The songs here listed are reflective of a whole spectrum of sad guitar songs, from throughout the 20th century, up to the turn of the century and beyond. Within, you will find a panoply of different styles and genres, some of which you may not necessarily have an interest in. Pick and choose to learn those that speak to you and act as a mentor and guide to you in your times of ailment.

Table of Contents

Sad Guitar Songs – Top 12

  1. ‘Creep’ by Radiohead
  2. ‘The Scientist’ by Coldplay
  3. ‘Hallelujah’ by Jeff Buckley
  4. ‘Lost Cause’ by Beck
  5. ‘While My Guitar Gently Weeps’ by The Beatles
  6. ‘Wish You Were Here’ by Pink Floyd
  7. ‘I’m So Lonesome I Could Cry’ by Hank Williams
  8. ‘Hurt’ by Johnny Cash
  9. ‘Knockin’ on Heaven’s Door’ by Bob Dylan
  10. ‘Wild Horses’ by The Rolling Stones
  11. ‘I Will Always Love You’ by Dolly Parton
  12. ‘Needle in the Hay’ by Elliott Smith

Placing best and sad beside each other in a sentence seems awfully antithetical, no? How can there be best sad guitar songs? Aren’t they all equally as sad, or best? Not as far I am concerned!

Some songs are sadder than others, and the quality of some is greater than those that they are often forced to rub shoulders with. Who’s going to look on as Elliott Smith rubs shoulders with One Direction and not at least slightly wince?

There is inherent value to sad guitar songs, for it is not just sadness that they instil in those listening and performing and absorbing. Often times, it is hope that is born of appreciating sad guitar songs, their power being to life affirm and to act as a shoulder on which to cry or lie during hard times. ‘Don’t talk, put your head on my shoulder. Come close, close your eyes, and be still’, as all round master of pop Brian Wilson would say.

In an era so rife with depression and its various offshoots – anxiety, paranoia – which is caused by and combines with our society’s latent addiction to technologies that, though useful, can be rather isolating, the power that sad guitar songs can have to raise our spirits and act as a shoulder upon which to lean is no laughing matter.

In fact, despite a burgeoning climate of dialogue regarding mental health and such, those suffering are often more likely to jam some earphones in than attempt to engage with others about their problems, especially with waiting lists for mental health services being so high.

1. ‘Creep’ by Radiohead

Though so often loathed by the band themselves after its release, this particular tune has become a favorite amongst fans of surface level independent rock music and sad guitar songs more generally. And for good reason, for it is an emotive and forlorn anthem to longing and low self esteem, both of which ought to be thoroughly relatable to any independent music consumer.

This tune was the band’s debut single, and the lead single for their debut album Pablo Honey, an album which would go on to sell very well because of this popular independent single picking up heat at the time.

The song’s subject matter is very specific, alleged by singer Thom Yorke to be about a drunk man watching a woman from afar, wanting to gain her attention though lacking the self confidence to make it happen.

This is something, however, that many can of course relate to, a sad sentiment that lurks inside so many of us. Like so much of the best pop music, a picture is painted abstractly enough for us to paint upon it our own feelings and images and experiences, though it is rendered no less potent for it.

The band would go on to write many more sad guitar songs, their style so characterised by a techno paranoid gloominess that they have garnered quite a reputation for being sad boys. While they abandoned this largely grunge and alternative rock influence style for more experimental pastures, it’s easy to see that these inherently downer tendencies were always present in their music.

The songs is entirely formed of four chords, G – B – C – Cm, relying more on texture than technical complexity, so do grab your axe and give it a go, making sure to wipe the fretboard of any tears beckoned by the playing of sad guitar songs.

2. ‘The Scientist’ by Coldplay

This is a by now ubiquitous hit from the old timers Coldplay. They are a world wide band who have been so swallowed up by attempts to remain relevant it’s hard to know exactly who they are or what they are intending to do in their musical ventures.

However, at one time they were reasonably humble folk who met at University College London, coming from various places around the United Kingdom (Devon, Southampton, London, Wales & Scotland). Their music was characterised by a mellow atmosphere and a signature use of space, all in all relatively harmless.

‘The Scientist’ comes as one of the singles from their sophomore album, the more mellow and lethargic of the roster. Though not strictly a sad guitar song, being most densely populated by broad, sonorous piano chord balladry, this fact hasn’t stopped countless droves recording covers on all manner of instruments, all types of guitars included. But, it’s actually one of the 8 easiest love songs to play on a guitar.

Much as with many other sad guitar songs, this more piano led number places at its centre the themes of loss, love, and forgiveness. This is expressed repeatedly with a wish to ‘take it back to the start’, which the adjoining music video takes literally, the entirety recorded in reverse, an effort perhaps to capture the sheer longing we all sometimes feel for returning to a previous moment, for turning back the clock and doing things differently with a loved one.

No, no, I’m fine, I’m not crying, no not at all, I’ve just got something in my eyes…

3. ‘Hallelujah’ by Jeff Buckley

This iconic song has been rinsed of its emotional potency by countless reality show covers attempting to imbibe it with a new lease of life. However, all we have to do is return to this classic to get a taste of what it must have felt like to write the song ourselves.

The song was originally written and recorded by Canadian singer songwriter and poet Leonard Cohen, released on his 1984 album Various Positions. Garnering little success initially, the song fell into the hands of John Cale, acclaimed artist extraordinaire and founding member of the Velvet Underground, who in turn recorded a cover that drew the attention of Jeff Buckley, who felt himself compelled to do the same.

Buckley did so on his only complete album, Grace, released in 1994, though the cover itself was released again in 2007, on the ten year anniversary of Buckley’s untimely death. The song gradually grew in popularity, peaking when it was used in the film Shrek in 2001, not to mention its re-release as a single later in the decade.

There are several different versions of the song that circulate, each artist performing tending to put their own spin on it. Cohen himself would perform different lyrics each time, allegedly having written many, many draft verses, all of which had a bent on religious imagery and allegory. This ambiguity and lack of official text encourages subsequent artists to reinvent the song for themselves in ways that they see fit and are ultimately relevant only to them.

This is a soulful tune that can be so many emotions depending on the performer, but it is undoubtedly one of those sad guitar songs that also makes for an incredible fingerpicking song too, composed as it is of ascending and descending arpeggios in 12/8 time.

If you’d like to play this song on the piano instead, I’ve got a blog post on the piano chords for Hallelujah.

4. ‘Lost Cause’ by Beck

Critics and fans alike are still reeling from Beck’s audacious and unprecedented side step from being the crown jester of oddity in independent and alternative scenes, to exposing himself and his tender heart like never before. Released merely as a promo single in the UK, Germany, and Japan, the song found more permanent and stable home amidst the folds of the adjoining album Sea Change, acting as the fifth track in the track listing.

Previously, Beck had revelled in making an all round mockery of himself and the music industry at large, with lyrics that poked right at the rotund bellies of capitalist label executives and their mantras, all over a bed of constantly shifting genre palettes and bizarre, previously unheard, combinations of styles and traditions.

However, on this album Beck laid himself bare, releasing a roster of 12 sad guitar songs for the mind, heart, and soul. The catalyst for such a major stylistic change comes from Beck himself having experienced a very major break up, clearly needing this format to explore these intense down beat feelings.

For the act of making sad guitar songs, much like listening to them, can be a real source of catharsis, laying bare all the feelings into sad guitar songs in much the same way as you might write them down on paper and close the respective book, so that you can move on and leave said memories in the past.

‘Lost Cause’ comes at a point in the album where Beck is finally coming to terms with the fact that the relationship in question is indeed a lost cause, stating that ‘he’s tired of fighting’ for something that he knows is a lost cause, thick and forlorn emotions almost choking his voice at almost every turn of the track, the mood heavy, the rhythm plodding and lethargic.

5. ‘While My Guitar Gently Weeps’ by The Beatles

For any Beatles fans, this song should come as no surprise on a list like this, putting many other sad guitar songs to shame in its bold displays of passionate angst. Considered by many to one of the Beatles most iconic songs, and by others to be one of the best rock songs of all time, this track earns a special place on this list as a highlight, up there with some of the best sad guitar songs of all time.

Initially written by George Harrison as a folk ballad, the song took new life among his fellow band mates, electrified by their song writing mastery. Eric Clapton features on the track, playing a blues guitar very passionately, though his deplorable acts and statements of racist intent prevent me from being in any way interested.

Instead, by comparison, I recommend the version performed by Prince and company at the 2004 Hall of Fame Induction Ceremony, wreaking of passion and swagger, Prince is a sex symbol for the ages.

The song itself deals with the Chinese ‘I Ching’, and there is a distinctly transcendental flavour to many of the lyrics, looking ‘at the world’ and noticing that ‘it is turning’, ascended and removed from such earthly matters. However, there is such an earthy and deep rooted yearning for earthly communion and unity throughout the song, the song’s solo almost playing the part of the tears of all the world, pouring representations of universal strife.

This is certainly one of the more difficult sad guitar songs on the list, and certainly one of the more outwardly angsty and passionate, though it is most certainly worth your time and patience in learning it. And if you haven’t yet heard it, I implore you to soak in it, absorb it, and be free.

6. ‘Wish You Were Here’ by Pink Floyd

This classic right here is bound to be one of those sad guitar songs that you hear played at least three times every time you visit a guitar store, or an acoustic guitar store more specifically. This is, logically, because the ratio of difficulty to emotive value is very low on the former side and conversely very high on the latter, packing quite the emotional punch.

This song stands as one of the most famous songs by English progressive rock band Pink Floyd, also one of their saddest, and one of several to deal autobiographically with the mental deterioration of founding band member and former lead singer Syd Barrett, others including ‘Shine On You Crazy Diamond’ (from the same album) and ‘Eclipse’ (the final track from their previous landmark album Dark Side of the Moon).

The story begins in the late 60’s, when Pink Floyd fronted by Syd Barrett were taking the London psychedelic scene by storm, though this wasn’t the only thing they were all taking. Inspired by the mantra of the movement and the times, Barrett was ingesting an excessive amount of the psychedelic Lysergic Acid Diethylamide. This initially had a very productive effect, both on his song writing and outlook on life, though eventually began to play tricks on him and his mental health.

He went into an absolute melt down, and his fellow band mates, instead of trying to support him and wait for his recovery, decided to out him from the band, and so he went to the English countryside, where he stayed until his death.

However, one day several years later he turned up at the studio as the band were recording this album, shocking, appalling, and saddening all those present through his drastic change in appearance, now bald, overweight, and dead between the eyes.

7. ‘I’m So Lonesome I Could Cry’ by Hank Williams

Hearts aren’t laid much more bare than Hank Williams‘. As Hank Williams songs go, this is certainly one of the most iconic, and up there with the most befitting of being listed as one of the best sad guitar songs.

The tune was recorded and released in 1949, eons ago, and yet still manages to touch the hearts of all who lay ears upon it. It was originally released as the A side to another single, ‘My Bucket’s Got a Hole In It’, following the contemporary tradition of coupling a sombre ballad type song with a more upbeat number, preferred as the latter was on jukeboxes.

The release came at a time when intense and personal emotions were not so commonly orated atop country music’s knack for simple and literal directness of expression. The song was instantly special and unique, one of those sad guitar songs that began life aflame and kept burning and burning as it was instilled into the hearts, hands, and voices of ceaseless waves of other musicians eager to reinvent the song for themselves.

The song uses to devastating effect the literary device of pathetic fallacy to instil in the surrounding landscape the emotions of the speaker. ‘The moon just went behind the clouds, to hide its face and cry,’ croons Williams, personifying the moon itself, morphing his own self into that of the moon, to soak up some of his own pain.

Firmly in the country style, which Hank Williams himself laid plenty of the foundations for, the song is composed simply, meaning that anyone could pick up the guitar and strum along, perhaps letting a neat humming croon slip from between pursed lips. It is this music’s stark and bare simplicity that it excels, welcoming all to imbibe it something of themselves, their own story up until this point in time.

8. ‘Hurt’ by Johnny Cash

This classic tune is another of those sad guitar songs that has been utterly reinvented from its initial context, accruing and swelling with new potency as a result. So revered is this reinvention that many don’t even realise that it is just that. So dearly beloved is this cover that many would never dare to believe that Johnny Cash himself had not written it, so reminiscent it is of the music of the work of his later period with Rick Rubin. And those who do acknowledge this as a cover are quick to state that it is indeed on the greatest ever put to tape.

The song initially was born of the industrial and noise rock band Nine Inch Nails, released mainly as a promotional single in 1995 for their much acclaimed sophomore album The Downward Spiral which was released the previous year. Though it received a fair amount of acclaim at the time, nominated for a Grammy Award for Best Rock Song in 1996, it was in 2002 that things really took off.

Rick Rubin suggested the idea of covering the song to Cash while recording the last album that would be released in his lifetime, the lyrics ever so reflective of the present state of Cash after a long and illustrious career influencing the annals of country and popular music at large. Trent Reznor, frontman for Nine Inch Nails, was approached and was initially hesitant, purely for thinking it might seem gimmicky.

He was soon won round, however, and is emotionally struck each time he watches the accompanying video, which so vividly represents the lyrics of the song in relation to Cash’s career, with images from throughout his lifetime. Footage of he and his wife, old and young, then in archival footage, and now captured as though in a vanitas painting, placing emphasis on the futility of human achievements, even with so vital a career as his.

The original is rather electronic and ambient in tone, sticking fairly strictly to Reznor’s intention for the adjoining album to be more textural, but Johnny Cash’s version is purely acoustic, ensuring its firm listing in this series of sad guitar songs.

9. ‘Knockin’ on Heaven’s Door’ by Bob Dylan

One would be hard pressed to find a music enthusiast who, even if not particularly fond of folk or rock music, doesn’t know or feel something within when listening to this particular track, so fond is it in all the annals of sad guitar songs.

Originally written in 1973 by Bob Dylan for a film about famous gunslinger Billy the Kid, the song has occupied the musical world and the world at large with a life of its own, covered by many famous artists. You might even be more familiar with the version popularised by Guns and Roses, in which lead singer Axl Rose takes many, many artistic liberties with the delivery of the vocals.

Much aligned with the simple, earnest American folk flavourings of Bob Dylan’s past efforts, the chords are themselves simple, basic, and soulful, mostly cycling between patterns of only three chords at a time, four chords overall, switching between G – D – Am & G – D – C.

As with a lot of the music in this vein, including plenty by Bob Dylan himself, much of the expression is in the vocals and the lyrics, so the strumming is relatively rudimentary and straight forward. This might even be an opportunity to seize the song yourself, making it your own.

If you’re comfortable singing and used to performing in this way, perfect! If not, then it is definitely worth trying if it is something you are interested in. These guitar songs with 4 chords are simple enough to encourage multi tasking in this way without detracting from the emotional potency, and I would suggest that of all sad guitar songs this would be a particularly poignant one in which to begin your journey to becoming a crooner.

10. ‘Wild Horses’ by The Rolling Stones

This is another of those sad guitar songs that has been covered relentlessly, however with the exception that it is the original that has remained the shining example of the song’s innate magic, though there are so many other songs with the title ‘wild horses’. Considered to be one of the best songs of all time, and certainly a signature of the Rolling Stones, this version and particular song is not to be forgotten.

This is a song that initially came into existence over the course of a three day song writing and recording session at Muscle Shoals Sound Studio in Alabama, between the 2nd and the 4th of December 1969. However, owing to legal and copyright complications, this song didn’t see the light of day until 1971, when it was released as a single in the summer and also as a part of the full length album Sticky Fingers.

The piece is purported to deal directly with lead singer and song writer Mick Jagger’s parting from long term partner, Marianne Faithfull, though Jagger himself vehemently denies this, stating: ‘I remember we sat around originally doing this with Gram Parsons, and I think his version came out slightly before ours. Everyone always says this was written about Marianne but I don’t think it was; that was all well over by then. But I was definitely very inside this piece emotionally.’

Key to this is the fact that a song can be born without an intended meaning, that a song can be written and lyrics can leave your mouth and mind without being premeditated, only gaining meaning afterwards, depending on the listener and the present performer. The meaning, like the horses, is wild and seemingly untameable, people even to this day discussing them avidly.

The song itself, like many sad guitar songs previously, sits firmly in the vein of country rock, featuring an acoustic guitar simply strumming in Nashville tuning, where the E, A, D, & G strings are strung one octave higher than in standard tuning. This, however, doesn’t mean that you need to do so. As it’s an octave, you can simply play it normally and it will just as good!

11. ‘I Will Always Love You’ by Dolly Parton

Yet another example of one of those sad guitar songs that took on new life at the hands of another artist; I bet you didn’t even know Dolly Parton herself wrote this original version. Besides showing us how to play guitar with long nails, she gave this song a particular tune.

Of course, ubiquitous is the version Whitney Houston sang in The Bodyguard, so repeated ad nauseum as to allow no one to rest from its sweet and gut-wrenching croons.

This song came to life in 1973 when it was written and recorded by Dolly Parton, released as a single on RCA records the following year in March. The song was a massive commercial success even at the time, reaching the very peak of the Billboard country charts twice, once upon the initial year of release, and then once more when it was rerecorded for the soundtrack of the film in which Parton starred, The Best Little Whorehouse in Texas, released in 1982.

This was far from the end of the story, however, for the song took on a whole new life when it was adopted and reinvented by Whitney Houston in the 1992 film The Bodyguard, taking on whole new meaning. It is often this version that many people quote and think of in popular culture, though the song has been covered many, many, many more times, both in its original form, in this reinvention, and even as a dance remix by Sarah Washington.

Originally written as a farewell to her then business partner and early mentor, Porter Wagoner, before she embarked on her own solo career, the song is so adaptable and has thus been adopted by droves of fans looking to expanding their roster of sad guitar songs. The original is entirely composed of just four chords – C, G, Em, & D – unlike the Whitney Houston version, famous for its dramatic key change, so this will be perfect for those wishing to serenade a loved one or simply oneself this coming Valentine’s Day.

12. ‘Needle in the Hay’ by Elliott Smith

What better way to round off this rousing roster of sad guitar songs than with an anthem by the late and great Elliott Smith? I could certainly have picked any song by this maverick of sad guitar songs, but this one has a special relevance to me, being the first tune of his I ever heard.

The first track on self titled sophomore album, Elliott Smith, we are introduced to the album’s universe through the gate keeping of this track, and everything you see within the rest of the work you see here. You also get the impression that this is very much the case from the fact that it was the only song to be released as a single to promote the album, to show on its own something of the album to the rest of the world, to entice them to enter this dark and gentle world.

Initially released on the 1st of January 1995, to promote the adjoining album released the summer of the same year, the song has taken on special relevance and meaning, with each succeeding generation of artists and fans alike praising Elliott and what he managed to capture on this song and the album at large.

The song details, with abstract and intentionally ambiguous and metaphorical word play, a teenager’s struggles with drug addiction, particularly that of heroin, obviously referenced in the song’s title, ‘Needle in the Hay’. These ambiguities allow Elliott to be specific to his own experience, while also permitting listeners to imbibe within it something of themselves.

The line ‘You ought to be proud that I’m getting good marks’, for example, could simply refer to grades at school and our parents’ instance that we get good ones, which any angsty teen (myself included) could and still can relate to. However, digging only the slightest bit deeper, we learn that marks in the context of heroin addiction are ‘track marks’, the physiological result of injecting the substance which leaves clearly visible marks all over the body. In this way, the word play sheds its skin before us, the entirety of the song being three dimensional like this.

I can’t count the amount of times I’ve relied on the sad guitar songs of Elliott Smith to get me through tough spots or points of destitute depression, so I hope he can in some way do the same for you. You are enough.

Final Tones

If any here were in any way doubtful of music’s ability to bolster the human spirit and stand beside us like apparitions in our times of need, then I sincerely hope that those doubters have come to terms with the facts.

In these tough and trying times, where often we are bound to our houses and unable to experience the joys of human interaction, warmth, and compassion, for some it is sad guitar songs that are the helping hand, extended outward to help the ailing on to another day.

Where would we be without the special power so bound up in music and song, that ever mystical force that we still know so little about spiritually, and yet has ever the most profound effect on us?

FAQs Sad Guitar Songs

What is the saddest song to listen to?

The beauty with sad guitar songs, like emotions themselves, are highly subjective and depend ultimately on all the parties involved. Emotions are singular and individual, different for every person, even if only slightly. Some may be incredibly moved by a ‘Let It Be’ or a ‘Someone Like You’, whereas some might find these songs too general to truly tug on their six heart strings.

What is the most saddest song in 2020?

This will no doubt be in the ear of the beholder, for like taste and subjectivity, emotions and the potency and feeling of certain songs will be different for every one. It seems with every passing year there is a greater amount of what would be termed ‘sad’, ‘downer’, or ‘depressing’ songs polling high on year end lists, largely because of how aware citizens of the West are becoming that they have been incredibly sad all along, and that capitalism isn’t doing them any favours…

What is the saddest guitar chord?

This is, again, extremely subjective though it is one of the best parts about music. It is so abstract an art form, one of the most abstract in fact – so intangible, so ephemeral – that there is still so much room to make it your own. The saddest guitar chord is entirely based on your own tastes, often out of your hands anyhow. Typically, minor chords are associated with sadness, or at least that’s how we are taught at an elementary level to think about the difference between the two.

How do you play sad songs on guitar?

With about as much feeling as you can muster. Even sad guitar songs have differences, there being various gradations to sadness. If you were to play ‘Cody’ by Mogwai with the amount of passion that Johnny Cash infects into just about any song he performs, it would feel completely anachronistic, so infected is Mogwai on the adjoining album with a sense of utter desolate downer misery. And vice versa.

What is the saddest sounding song?

This is ultimately entirely subjective, as every piece of music or even sound is so bound up in our interpretation of them that it’s essentially impossible to declare which songs are the saddest sounding songs, and which songs are sad guitar songs will very much depend from person to person. We are only the authors of our own experience, and even then it feels as though so much is out of our control!

What are the top 5 sad songs?

Again, this will be entirely subjective, depending on the person and their place in the world, for I doubt that many people in the East find whiny, depressing sad guitar songs from the West particularly emotionally stimulating or life affirming. My personal list would go (in no particular order) something like: ‘Good To Go’ by Elliott Smith, ‘The Purple Bottle’ by Animal Collective, ‘Puff (Up in Smoke)’ by Kenny Lynch, ‘Helpless Child’ by Swans, & ‘Tapestry from an Asteroid’ by Sun Ra. What about yours?

By Nate Pallesen

Nate is just your average (above average) guitar player. He's no Joe Satriani, Jimi Hendrix or Jimmy Page - wait this site is about acoustic guitars (sorry) He's no Django Reinhardt, Chet Atkins, or Michael Hedges, wait? who!? He's no Robert Johnson, Eric Clapton or Ben Harper - more familiar? Anyway you get the point :-)

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