A Smorgasbord of Sad Songs

As our regular readers know, I love music and I love lists.  Once again, those two loves converge as I share my list of "Best Sad Songs".  This topic should surprise no one given my previous admissions that I have a soft spot for sad or poignant lyrics.  As I developed this list, it become virtually impossible to rank them in order - especially since this list crosses multiple decades and genres - so I will just be listing them in alphabetical order.  Some of these songs are probably obvious choices, but I think some of them may be little obscure or unexpected.  Regardless, I hope you enjoy going through the list and, perhaps, you can be exposed to some songs you weren't familiar with and that will be added to your playlists.

So, let's crack open a cold one and all get depressed together...

Song: "A Home"
Songwriter(s): Maia Sharp, Randy Sharp
Artist(s): Dixie Chicks
Sample Lyric(s): "And I listened to my pride/When my heart cried out for you/Now everyday I wake again/In a house that might have been a home" and "They say home is where the heart is/If the exception proves the rule I guess that's true"
Comments: This tear jerker comes from the Chicks' criminally underappreciated third album Home, of which it is essentially the title track.  It was never released as a single, though it might have been if it hadn't been for the ridiculous backlash against the band after comments made overseas about President Bush.  Like the rest of the album, it features only acoustic instruments (with prominent dobro and mandolin) and beautiful, aching three part vocal harmonies.  The lyrics talk of regret for walking away from a relationship and regretting that the singer now lives in a lonely house that could have been so much more - a home.

Song: "A Long December"
Songwriter(s): David Bryson, Adam Duritz, Charlie Gillingham, Matt Malley, Ben Mize, Dan Vickrey
Artist(s): Counting Crows
Sample Lyric(s): "Maybe this year will be better than the last" and "The feeling that it's all a lot oysters, but no pearls"
Comments: A pensive, wistful song, this was the band's last top 10 hit and it is my favorite song by them.  It meshes downcast lyrics with a hint of hopefulness and a singalong "na na na na na" refrain. Even though the song prominently mentions California, it also captures the bleakness of winter.

Song: "Angel"
Songwriter(s): Sarah McLachlan
Artist(s): Sarah McLachlan
Sample Lyric(s): "There's always some reason to feel not good enough" and "Fly away from here/From this dark, cold hotel room/And the endlessness that you fear"
Comments: Because McLachlan is so adept at crafting sad songs, it was difficult to narrow it down to one or two choices.  However, I've always found "Angel" to be a deeply affecting song.  It's arrangement is very sparse - it's just McLachlan's gorgeous vocal backed by a piano - and that makes the lyrics about loneliness and a desire to escape that much more poignant.  McLachlan claims that the song was inspired after reading stories about musicians turning to heroin as a way of coping with the pressures of the music industry.  McLachlan's angelic voice (I hope some of the angels in Heaven sound like her) softly soars while the subject of the lyrics slowly slips downward and the contradiction makes the whole song that much more haunting.

Song: "The Bird Hunters"
Songwriter(s): Evan Felker
Artist(s): Turnpike Troubadours
Sample Lyric(s): "My hands around a Belgian made Browning/My mind on the lines of her face" and "The old dog had pointed while part of me died"
Comments: For the past six or seven years, I've been obsessed with Turnpike Troubadours.  Songs like this one are part of the reason why. Instead of writing a paint-by-the-numbers heartbreak song, Felker uses a hunting trip with a childhood friend and his dog as the backdrop for the narrator coming to terms with the end of a relationship. The song is a waltz that's propelled forward by typically terrific fiddle work by Kyle Nix. Felker has a knack for creating characters that feel three dimensional and lived-in and "The Bird Hunters" is an example of that.

Song: "Black"
Songwriter(s): Eddie Vedder, Stone Gossard
Artist(s): Pearl Jam
Sample Lyric(s): "I know you'll have a beautiful life/I know you'll be a star/In somebody else's sky/But why, why, why can't it be, can't it be mine?"
Comments: This is my favorite Pearl Jam song (as has been previously disclosed) but it also a very sad song.  It's about the end of a relationship and, rather than being bitter or angry at his ex, the narrator instead wishes her well despite the loss of her in his life.  While the song has been a fan favorite since it appeared on Ten more than a quarter of a century ago, it was never released by the band as a single because they thought it was too personal and fragile. You can feel the anguish in Vedder's voice, especially toward the end.  Powerful stuff.

Song: "Cat's in the Cradle"
Songwriter(s): Harry Chapin, Sandra Chapin
Artist(s): Harry Chapin, Ugly Kid Joe
Comments: This is a song where the sting of the song isn't a single lyric or line but rather the totality and irony of the entire narrative.  In the first few verses, a young boy wants to spend time with his father, though the latter is too busy to do so.  In the last few verses, the tables have turned.  The son is grown and the father (who is old and retired) wants to spend time with him, but now the son is too busy to do so.  The son turns out to emulate the father, though not in a good way.  The song hit #1 in late 1974 and then unexpectedly hit the top 10 again 19 years later when it was covered by rock band Ugly Kid Joe.  Interestingly, it likely means that someone who related to the young man the first go around would likely relate more to the old man when the cover was released.

Song: "Eleanor Rigby"
Songwriter(s): Paul McCartney (though it is attributed to John Lennon and Paul McCartney)
Artist(s): The Beatles
Sample Lyric(s): "Eleanor Rigby died in the church along with her name/Nobody came/Father McKenzie wiping the dirt from his hands as he walks from the grave/No one was saved."
Comments: One of the more radical songs at the time of its release (prominent string quartet and no other instruments), it is a melancholy song that lyrically and musically creates a picture of two lonely people who appear to exist in proximity to one another but yet never connect to ease their respective loneliness.  While McCartney was sometimes criticized for only writing sappy love songs, this song proves his ability to craft something much darker that still connects with listeners.

Song: "The Freshmen"
Songwriter(s): Donny Brown, Doug Corella, J.J. Douglas, Brad Vander Ark, Brian Vander Ark
Artist(s): The Verve Pipe
Sample Lyric(s): "We never talk of our lacking relationships/And how we're guilt stricken sobbing with our heads on the floor" and "For the life of me I cannot believe/We'd ever die for these sins"
Comments: No one really knows exactly what this song is about.  Abortion? Suicide? Even the band's lead singer and predominant song writer has given conflicting accounts over the years.  Regardless, it is a song about young people making mistakes and never imagining how grave and long lasting the consequences of those mistakes would be.  Just because you are young and seemingly invincible, your actions still have consequences.

Song: "The Funeral"
Songwriter(s): Evan Felker, Mike McClure
Artist(s): Turnpike Troubadours
Sample Lyric(s): "Ain't nothing like a family to make you feel so damned alone" and "Why's it take a funeral, boy, to bring you back to town?"
Comments: This is another gem by Turnpike Troubadours.  It tells the tale of Jimmy, a black sheep son who returns to his small town home for the funeral of his father.  The rest of the family doesn't care much for Jimmy or his girlfriend (who is described as a burned out Betty Paige who might have been pretty if she were half her age) who come back to the small town in a car that they stole.  Jimmy apparently hasn't been home for a long time and the song ends with his mother asking him why it took his father's funeral for him to actually come back around.  The lyrics provide little nuggets of detail throughout to the point where you can totally picture the characters and how they interact.  This song was not one that initially jumped out at me, but upon repeated listenings, it became one of my favorites.  Virtually every family (at least extended families) have a Jimmy, so I think everyone can relate to the characters that Felker and McClure have created.

Song: "Ghost in this House"
Songwriter(s): Hugh Prestwood
Artist(s): Shenandoah, Alison Krauss
Sample Lyric(s): "I don't live in these rooms, I just rattle around"
Comments: The first of back-to-back entries by Prestwood, this song talks about attempting to move on after the end of a relationship and paints a portrait of a heartbroken person who is little more than a ghost.  The Alison Krauss version is particularly moving as her feathery, angelic vocal (yes, like Sarah McLachlan, she has the voice of an angel) paints a picture of loneliness, depression and despair.  It's depressing as hell while also being hauntingly gorgeous.

Song: "Hard Rock Bottom of Your Heart"
Songwriter(s): Hugh Prestwood
Artist(s): Randy Travis
Sample Lyric(s): "I keep waiting for you to forgive me/You keep saying you can't ever start/And I feel like a stone you have picked up and thrown/To the hard rock bottom of your heart" and "I need your love, I miss it/I cant go on like this, it hurts too much."
Comments: A massive #1 hit for Randy Travis in 1990, this song is told from the perspective of a man who was unfaithful but who is now trying to seek forgiveness from his wife.  She can't bring herself to do so and it's causing him to become more despondent.  Country music has a long history of sad songs about cheating, but this one is unique in being more about the impact of a lack of forgiveness than the infidelity.  Prestwood wrote great lyrics and Travis delivers a stellar vocal performance.

Song: "He Stopped Loving Her Today"
Songwriter(s): Bobby Braddock, Curly Putman
Artist(s): George Jones
Sample Lyric(s): "He stopped loving her today/They laid a wreath upon his door/And soon they'll carry him away/But he stopped loving her today"
Comments: As expressed above, country music has a long history of sad songs, more so than any genre of music, with the possible exception of the blues.  This song may be the most famous of those.  In it, a man says he will love his lady until he dies.  And he does, even after she passes away.  His devotion to her remains strong.  The kicker is that "he stopped loving her today" because he died, thus fulfilling his promise.  The lyrics are great but it's George Jones' skilled, mournful vocals that helped push the son to the top of the charts years after his prime and make it one of the most loved country songs of all time.

Song: "Highway 20 Ride"
Songwriter(s): Zac Brown, Wyatt Durrette
Artist(s): Zac Brown Band
Sample Lyric(s): "And a part of you might hate me/But, son, please don't mistake me/For a man that didn't care at all."
Comments: Written essentially as a letter from a divorced dad to his son whom he travels Interstate 20 every other weekend to see, this song is a moving piece that helps illustrate the difficulties of divorce.  The narrator tries to explain himself to the boy, while acknowledging that the son may very well hold a grudge against him for not being there every day.  In lesser hands, the song could have come across as syrupy or schmaltzy, but the mournful fiddle and Brown's almost pleading vocals instead make it a powerful, honest song.

Song: "How Can I Help You Say Goodbye?"
Songwriter(s): Karen Taylor Good, Burton Banks Collins
Artist(s): Patty Loveless, Laura Branigan
Sample Lyric(s): "How can I help you say goodbye?/It's okay to hurt and it's okay to cry."
Comments: One of the more melancholy country songs of the 1990s, it presents the narrator dealing with having to say goodbye at three different points of her life, each time being consoled by her mother. In the first verse, she is a little girl moving away from her best friend. In the second verse, she and her husband are packing up things as they divorce.  In the final verse, as she is at her mother's bedside as her mother prepares to pass away.  It's a blatant attempt to bring tears to your eyes, but darn it if the lyrics and vocal performance (at least in the Loveless version) don't fail to deliver the goods.

Song: "I Just Wasn't Made for These Times"
Songwriter(s): Brian Wilson, Tony Asher
Artist(s): Beach Boys
Sample Lyric(s): "I keep looking for a place to fit/Where I can speak my mind" and "Sometimes I feel very sad."
Comments: The Beach Boys are best known for upbeat, happy, surfing songs, which is ironic given the well publicized depression, substance abuse and mental health issues experienced by band founder and creative force Brian Wilson.  This song, which appears on the band's iconic Pet Sounds album, is the antithesis of "Fun, Fun, Fun" and "Surfin' Safari."  It is about depression and social alienation, how Wilson (despite his incredible talents) always felt like an outsider who didn't belong.  With Wilson's falsetto vocals backed by harmonies from the rest of band, it is a haunting, sobering number from a band best known for sunny pop songs.

Song: "I See It Now"
Songwriter(s): Larry Boone, Paul Nelson, Woody Lee
Artist(s): Tracy Lawrence
Sample Lyric(s): "Holding him, you've never looked more beautiful/Letting go has been so hard on me"
Comments: A lovely little waltz, this song is a quintessential example of "don't know what you have until it's gone." A man sees his ex out with her new love and he realizes what he had and how much he misses her.  It's not a unique sentiment at all, but with the prominent, lonesome fiddle and Lawrence vocals, it's well done and a cut above what you might otherwise expect if you just saw the lyrics on a piece of paper.

Song: "I'm So Lonesome I Could Cry"
Songwriter(s): Hank Williams
Artist(s): Hank Williams
Comments: The oldest song on this list, it is the forebearer for all of the sad country songs that came after it.  No less an authority than Elvis Presley called it "probably the saddest song I've ever heard." With an endorsement like that, what more do I need to say?

Song: "The Living Years"
Songwriter(s): Mike Rutherford, B.A. Robertson
Artist(s): Mike + The Mechanics
Sample Lyric(s): "I wasn't there that morning when my father passed away/I didn't get to tell him all the things I had to say"
Comments: A huge hit around the globe in early 1989, this melancholy number is backstopped by a repetitive guitar hook supporting typically terrific vocals from Paul Carrack.  (This guy has to be one of the least known lead singers who sang lead vocals on numerous hit songs for several different groups.)  The lyrics are of a man reflecting on miscommunication and an inability to reconcile differences with his late father.  I think everyone has regrets about things they never got to say to a loved one before they passed away and this song perfectly captures that sentiment.  I'm not crying - you're crying!

Song: "Lyin' Eyes"
Songwriter(s): Glenn Frey, Don Henley
Artist(s): Eagles
Sample Lyric(s): "She gets up and pours herself and strong one/And stares out at the stars up in the sky/Another night, it's gonna be a long one/She draws the shade and hangs her head to cry"
Comments: This one may surprise you, in that most people probably don't think of it as a sad song.  But, when you consider the story it tells, it is definitely a sad song.  It's about a woman who marries a wealthy older man for his money as opposed to love.  She has an affair with a young man across town, but she still returns home to an empty house every night.  Her life is a lie but she tries to put on  brave face to the world.  It's a pretty bleak character study and that's why it makes my list.

Song: "Memories and Rust"
Songwriter(s): James Dunning
Artist(s): Lost Immigrants
Sample Lyric(s): "I'll take this wheel at 10 and 2/Grip it with all my might/On the dash a picture of you/And I'll drive you out of my life/Take you to the end with me/Leave you in the dust/Drive you out until I'm free in this old heart/Of memories and rust"
Comments: A little known gem from a little known Texas Country band, it's a song about heartbreak and trying to move on from that.  As someone who spent many a night driving on country roads outside of Waco, Texas during college, singing along to sad songs, the chorus and general sentiment of this song absolutely speaks to me.  Lost Immigrants have a number of really good songs, but this one is my favorite of theirs.

Song: "Neon Moon"
Songwriter(s): Ronnie Dunn
Artist(s): Brooks & Dunn
Sample Lyric(s): "Now if you lose your one and only/There's always room here for the lonely/To watch your broken dreams/Dance in and out of the beams/Of a neon moon"
Comments: This is the archetypal sad country song of the 1990s.  A lonely man drinking his blues away in the corner of a bar lit only by neon signs.  Is it cliché? Sure.  Is it still effective? Heck yeah.  I stumbled across this song during my freshman year of college (when I was still very much a neophyte country music fan) and it was one of the first non-Garth Brooks songs that I learned the words to.

Song: "New Way to Fly"
Songwriter(s): Garth Brooks, Kim Williams
Artist(s): Garth Brooks
Sample Lyric(s): "A new way to fly/Far away from goodbye/Above the clouds and the rain/The memories and pain/And the tears that they've cried"
Comments: As crazy as it sounds, this song is the song that made me fall in love with country music.  Growing up, I had basically no exposure to country music.  My parents listened to The Beatles, The Beach Boys, Fleetwood Mac, etc. rather than Hank Williams and Merle Haggard.  When I was first introduced to Garth Brooks, people played up his more pop/rock stuff like "The Thunder Rolls."  But it was this sad country song that somehow grabbed me and dragged me in.  It uses bird imagery (like birds on a high line) to paint a picture of a bunch of sad, lonely men lined up at a bar who are trying to find a way to escape (or fly away from) their heartbreak.  It's nothing too unique, but without this song, I may never have heard many of the songs on this list.  As such, it's always occupied a little corner of my music loving heart.

Song: "No One is to Blame"
Songwriter(s): Howard Jones
Artist(s): Howard Jones
Sample Lyric(s): "Your aspirations in the clouds but your hopes go down the drain"
Comments: Few things in life are sadder than unrequited love.  One of the few things that ARE sadder is when two people love each other but are kept apart by bad timing or other circumstances.  This song paints that picture incredibly well - using a number of metaphors to illustrate how close one can be without getting to fulfill one's desires. He loves her and she loves him but they can't be together and it's no one's fault. This song still gets me 30+ years after I first heard it.

Song: "Nobody's Home"
Songwriter(s): Clint Black
Artist(s): Clint Black
Sample Lyric(s): "A cup of coffee in the morning/It's just food for the brain/I've been numb since our last goodbye/Haven't felt a thing"
Comments: The song describes a heartbroken man who is just going through the motions and routines of his life but who has ceased to live. He still dresses and combs his hair the same way but everyone agrees that he's just a shell of his former self. "The lights are on but nobody's home."

Song: "One"
Songwriter(s): James Hetfield, Lars Ulrich
Artist(s): Metallica
Comments: You didn't see this one coming, did you?  A thrash metal song as a sad song? Absolutely. The lyrics tell of a soldier wounded in battle who has lost his arms and legs and been left blind and deaf.  He's trapped inside his own mind and is only being kept alive by machines.  He wants to be allowed to die but can't communicate with anyone to make that desire known. It's dark stuff - as is often the case this genre of music - and is unquestionably sad.

Song: "Porcelain"
Songwriter(s): Kevin Griffin
Artist(s): Better Than Ezra
Sample Lyric(s): "Well I wish I could kill you, savor the sight/Get into my car, drive into the night/Lie as I scream to the heavens above/That I was the last one you ever loved"
Comments: This is a lesser known Better Than Ezra song off their debut album, Deluxe, which is one of my favorite albums of all time.  While it was never released as a single and wasn't a hit like "Good", I've always loved this song. Like many of the songs on this list, it's about someone trying to move on after the end of a relationship but they just can't seem to do so. In this instance, the narrator's ex-love has moved on and is with someone else and he wants to put her in her place and walk out the door, but he just can't do it because he's still entranced by her ("your skin is like porcelain").  Instead, he fantasizes about killing her just so that he could claim that he was the last one she ever loved, even though he knows that is a lie.  It's a dark, depressing sentiment that is presented with an aching vocal by Griffin and light, acoustic guitar accompaniment. It shows that a song can be both heartbreaking and beautiful at the same time.

Song: "Sign on the Door"
Songwriter(s): Edwin McCain
Artist(s): Edwin McCain
Sample Lyric(s): "We all talk about timing, lifestyles and such/But to a heart that's been shattered, those words don't mean much"
Comments: When most people think of Edwin McCain, they likely think of ballads like "I'll Be."  True fans of his, however, know that he has a number of funkier, upbeat songs with horns.  This particular song is neither a ballad nor a funky, upbeat number.  It is a straight out blues number, complete with bluesy guitar work by Larry Chaney. It starts out slow and builds into a crescendo of McCain's soaring, soulful vocals above Chaney's bluesy shredding.  Lyrically, it's about two people with broken hearts who might have been together but for whom the times just didn't work out.  It uses a metaphor of a sign on the door saying "Sorry, we're closed" for a person's heart not being open for love or a relationship at the time. I've been a big fan of McCain's since I saw him play at a little club in Dallas, TX opening for Hootie and the Blowfish in February 1995 and this is one of my favorites by him.

Song: "Someone Like You"
Songwriter(s): Adele Adkins, Dan Wilson
Artist(s): Adele
Sample Lyric(s): "Don't forget me, I beg" and "Sometimes it lasts in love but sometimes it hurts instead"
Comments: No list of a sad songs would be complete without at least one song from Adele, the British chanteuse who has produced a long litany of heartbreakers.  Her smoky and then soaring vocals convey her heartbreak while the lyrics paint a picture of a woman who still yearns for an ex-lover who has moved on and married someone else.  The subject matter (the song was co-written with Dan Wilson of Semisonic - "Closing Time" - fame) is nothing unique and in the hands of a lesser singer, it might have been cheesy or too syrupy.  But Adele's voice conveys the emotions so well and the simple piano accompaniment backs it up and it all works splendidly.

Song: "Sorry to a Friend"
Songwriter(s): Edwin McCain
Artist(s): Edwin McCain
Sample Lyric(s): "We had wonderful times but terrible timing"
Comments: This song has appeared on previous music lists that I have done because it is one of my favorite songs of all time and it is near and dear to my heart for reasons that shall remain unspoken. As I've alluded to earlier in a couple of songs, few things are sadder to me than two people who feel the same way about each other but who are kept apart by circumstances or bad timing. This song encapsulates and - especially the sample lyric above - captures that sentiment perfectly.  The two subjects of the song apparently haven't seen each other for two years, but it's obvious that they had very strong feelings for each other in the past but things never worked out.  They were extremely close friends who could have been more than that, but for whatever reason, it just never happened.  Now they have moved on with their lives and all they can say to each other is that they are sorry that they were never able to be together. McCain conveys the sentiment lyrically and through his vocals and this song never fails to hit me right in the heart.

Song: "Tears in Heaven"
Songwriter(s): Eric Clapton, Will Jennings
Artist(s): Eric Clapton
Comments: In the Spring of 1991, Clapton's four year old son died from the window of a high rise apartment building in New York City.  In response, Clapton wrote this song as part of his healing process to recover from his son's death.  Though Clapton is predominantly known for his electric guitar riffs during his solo career as well as his time with Cream and Derek & the Dominos, this song is a soft, quiet number primarily just consisting of Clapton's vocals and acoustic guitar. It became the biggest hit of Clapton's illustrious career and Clapton later admitted that the song and how people connected with it helped him heal from the tragedy that occurred.

Song: "Travelin' Soldier"
Songwriter(s): Bruce Robison
Artist(s): Bruce Robinson, Dixie Chicks
Comments: Another story song that paints a picture of two people kept apart by circumstances - in this case, the Vietnam War.  It tells the story of an 18 year old young man dressed in his Army green reaching out to the waitress at a local café (described as a girl with a bow in her hair). They get to know each other and then he tells her that he's about to leave for the Army and asks if he can write letters to her while he's gone. He does so and she falls for him through the letters. As it turns out, the young man dies in Vietnam and it seems like the girl with the bow in her hair is the only one who even cared. The song conveys a since of loneliness for both the young man and the girl and that shared loneliness is part of what led them together, only for Uncle Sam to intervene and keep them apart. 

Song: "Whiskey Lullaby"
Songwriter(s): Bill Anderson, Jon Randall
Artist(s): Brad Paisley and Alison Krauss
Sample Lyric(s): "She put him out/Like the burning end of a midnight cigarette/She broke his heart/He spent his whole life trying to forget"
Comments: If Shakespeare lived in modern Nashville, Tennessee and he wanted to write a country version of "Romeo and Juliet," it might turn out something like this.  The first verse (sung by Paisley) tells of a man who got rejected by the woman he loved and then proceeded to drink himself to death to deal with the pain. The second verse (sung by Krauss) tells of the aforementioned woman who is so guilt stricken by what happened that she likewise proceeds to drink herself to death.  The man and woman wind up being buried side-by-side under a tree. The two verses have an interesting symmetry as the two main characters' stories unfold and the two singers harmonize and deliver understated vocal performances that don't overwhelm the lyrics.

Song: "(Who Says) You Can't Have It All"
Songwriter(s): Alan Jackson, Jim McBride
Artist(s): Alan Jackson
Sample Lyric(s): "A stark naked lightbulb hangs over my head/There's one lonely pillow on my double bed"
Comments: It only makes sense to finish off a list that has been largely dominated by country songs with a song co-written and performed by one of the biggest country stars of the past 30 years. While this wasn't one of Jackson's biggest hits, it's always been one of my favorites of his.  It paints a picture of a broken-hearted man who lives in a lonely room whose walls are decorated by pictures of and letters from the woman who left him.  He refers to his sad surroundings as a "fool's Taj Mahal" and ironically implies that he has everything that he needs. It's a sad, downcast song dripping with steel guitar, a perfect example of how good a sad country song can be.

There's my list.  What sad songs are on your list?  What songs did I miss?  I'd love to hear your feedback!

Thanks for reading!