The 20 Best Depressing Country Songs

Every few months I get on a music kick, usually triggered by something, that results in me gobbling up a plentiful dose of a certain kind of music from a certain genre, usually from a certain timeframe.   The combined triggers of a miserable love life and the empty, dark hours of winter have recently pushed me straight into the throes of stone cold country music heartbreakers.  Now an important distinction has to be made about what I'm going for here.  I love tearjerker country songs and thematically dark country songs, and sometimes those songs overlap with the depressing "downer" songs I'll be profiling below, but this list is comprised entirely of songs that don't drive me to tears or goose bumps, but which accommodate a tearless yet mellow and defeated mood with their lyrics and arrangement.  To the people who don't like country music because it's "depressing", these are the exactly the kinds of songs they're talking about.  But to those of us who feed off of emotional dysfunction, these are the kinds of songs that make country music exceptional.

I was planning to make a top-25 list here but honestly couldn't find 25 songs that genuinely fit this list's limitations.  There are literally fewer than two dozen songs out there that I run to when seeking to feed a sadness fix, at least for songs released as singles.  I have a considerably larger number of songs on this pedigree as album cuts from my CD collection, but I'm only counting songs released as singles here.  It's quite fascinating how many first-rate singers who would seem capable of recording a perfect downer of a song never have, at least not as a single.  Crystal Gayle and Don Williams' musical legacy doesn't consist of such a song.  Nor does Martina McBride who has a number of dark and tearjerking songs, but her songs that are simply downers were not worthy of making this list.

And when comprising this list, I couldn't help but notice that none of these songs predate my birth in 1977.  Obviously there are a lot of great downer country songs from before my era, but it's harder for me to connect with most of those songs especially on the arrangement front.  Country music production values progressed considerably in the mid-1970s and the quality of the musical arrangement is often just as consequential to a good depressing country song as are the lyrics.  And even among songs from my era, some songs just don't take me down personally the way they do others.  For instance, George Jones' "He Stopped Loving Her Today" would be the song that most country music aficinadoes would rate as the hands-down best song to fit this list's metric.  While acknowledging that it's a great song, it doesn't hit me the way the songs on my list do.  Ditto for Dolly Parton's "I Will Always Love You", an indisputable country classic that for whatever reason just doesn't hit me in the gut.  And contemporary crooners who pride themselves for their mastery of these honkytonk weepers like Alan Jackson and Mark Chesnutt have a bunch of really good songs that qualify for my list, but nothing that I find myself specifically turning to when looking for a downer country song fix.  And another song that I've always loved that fits this criteria is Gary Allan's "Smoke Rings in the Dark".  Here's a song that's among my top-100 country songs of all-time, but for me it doesn't work as a bring-me-down in the sense of many others.  Needless to say, the list is kind of hard to define in a measurable way....it's just based on my personal instinctive reactions to certain songs.

With those qualifiers out of the way, here's my top-20 list which I will begin with two "honorable mentions" for songs I couldn't go without discussing....

Honorable Mention #1.  Not a Day Goes By--Lonestar (2002).....Fewer songs qualify for my list in a more tangible way than this top-5 Lonestar ballad from last decade, but I still couldn't quite bring myself to put it in the top-20 because it's a little bit over-the-top in a "drippy" way.  Richie McDonald's powerhouse vocals shone brightly as always, but in this case overshot the runway, at least for it's impact on being a true "downer" song.  Still, it doesn't get much more deliciously depressing than the lyric "I still wait for the phone in the middle of the night...Thinkin' you might call me if your dreams don't turn out right".

Honorable Mention #2. Sticks and Stones--Tracy Lawrence (1991)....The ascent of Tracy Lawrence came at the tail end of country music's New Traditionalist era, and managed to persevere well into the "Hot New Country" era with a decidedly traditional country sound and song selection.  But the most impactful song of his career was this midtempo ballad about a man lamenting the heartbreak of a marriage at the onset of its dissolution with a clever lyrical hook about their broken home that "these sticks and stones may break me, but the words you said just tore my heart in two".

#20. I'd Rather Miss You--Little Texas (1993).....Very few would equate the musical legacy of Little Texas, a Hot New Country-era hybrid of 80s hair bands and pale Eagles ripoffs, with greatness, but they had one song that in my opinion stood out amongst the rest of their body of work, and interestingly it was not one of their biggest hits, only going top-15 in the summer of 1993.  A perfectly melancholy musical arrangement accompanied solid harmonies and the great lamenting lyrics of "If I have to choose between living without you and learning to love someone new...Then I'd rather miss you".

#19. Some Fools Never Learn--Steve Wariner (1985)....Steve Wariner was one of the pioneers of the modern mellow heartbreak classic, his smooth voice and guitar wizardry combining to make some of the best country music of the 80s.  The best song of his career was 1987's "The Weekend" and in all honesty that song should be on this list but because of its thematic similarity with another ahead on the list, I decided to go instead with this very relateable downer about a guy who keeps going for the wrong girl and sets himself up for inevitable heartbreak time and time again.

#18. I Never Quite Got Back From Loving You--Sylvia (1984).....For my tastes, the 80s were the heyday of depressing country songs, with the right mix of capable, distinctive vocalists and musical arrangements with just the right level of production (there was too little production in country music before the 80s and too much after the 80s).  Sylvia had a number of great sad songs, all brilliantly sung, but the purest heartbreaker of her career was this 1984 ballad where the narrator can't move on from a broken relationship and is "still out there...in that world you took me to".

#17. One Solitary Tear--Sherrie Austin (1997)....Australian-born country singer arguably overpowers the vocals a bit on the choruses here, but the case could also be made that she sold a more believable emotional attachment to the song with the power vocals.  Either way, it's a great song where every little nugget of the daily grind is a reminder of love lost, best illustrated with the lyric "The mailman still brings all your catalogs...The radio just keeps on playing our songs".

#16. Addicted--Dan Seals (1988).....Dan Seals vocal stylings were perfect for these kinds of songs, and he knew it as clearly they were in both his vocal and songwriting wheelhouse.  In this song, a woman in a one-sided marriage drives herself delirious with despair and a slow-motion trainwreck of coming to terms with a husband who doesn't love her.  Some of the rawest anguish ever conveyed in a commercial country song along with a memorable chorus assured this song would make my list.

#15. Home Ain't Where His Heart is Anymore--Shania Twain (1996)....For my tastes, Shania Twain was a net negative for country music by forcing a rising emphasis on image over substance coupled with the mostly immature body of musical work that she brought to the table.  But the one song of her career that was a true gem was this mellow ballad from her breakthrough album that nobody would ever describe as immature.  The narrator's grief is less raw and self-destructive as the narrator from the previous song on the list, but the sorrow of a loveless marriage is conveyed well its own way, coupling fond memories of the good old days with the pure exhaustion present-tense of trying to make something work that isn't working anymore.

#14. Inside--Ronnie Milsap (1983)....Nobody else in the world of country music was better positioned to make the stylistic leap into the country music of the 1980s than Ronnie Milsap with his wide vocal range and being his generation's premier maestro of the keyboard.  Couple that with Ronnie's long-standing preference for some of the saddest heartbreak songs ever set to music and you had a match made in heaven.  The musical arrangement here was one of the most sophisticated for any country songs at the time and it's "tear in my beer" musical grooves really punch the listener in the gut when "Suddenly it occurs to me...she's trying to say goodbye" even though the listener pretty much knew that before the narrator's epiphany.

#13. Why They Call it Falling--Lee Ann Womack (2001)....While her album cuts are full of awesomely depressing ballads to the point of making her this generation's top auteur of sad songs, Lee Ann Womack never released too many of her unparalleled downer songs as singles.  But the song that was easily the darkest of her career was also the most depressing, particularly given how bubbly and flowery it starts.  But after the second verse, reality sets in and the narrator who was previously "walking on the ceiling" gets the answer to the song's core question after darkly acknowledging that "It's a holler...it's a cave...it's kind of like a grave....when he tells you that he's found somebody knew."

#12. Has Anybody Seen Amy?--John and Audrey Wiggins (1994).....Most songs on this list are about love lost, but the outlier of the group is this tale of a narrator's return to a hometown that he no longer recognizes and feels empty and alone in, sung by the underrated brother-sister vocal duo who never had a major hit besides this song.  There are a couple brilliantly haunting arrangement riffs in this song that add to "lost in his own hometown" lyrical overtones where "I can't see the stars through the neon lights".  I always look back at 1994 as the best individual year in country music history, as it's a shame that a song this good mostly got lost in the shuffle a generation later.

#11. Rose Bouquet--Phil Vassar (2001)....One of the most promising starts to a country career came with the first-rate debut album of singer-songwriter Phil Vassar.  He has in no way lived up to the high standard of that rookie effort with subsequent albums, but nothing will take away from the extent to which Vassar hit the ball out of the park in his first at-bat.  And he earned a berth in the depressing country song Hall of Fame with this nicely arranged weeper that looks at lost love through the prism of a magical wedding day where everything seemed so perfect until "we threw it all away like your rose bouquet".

#10. My Heart Will Never Know--Clay Walker (1995).....Clay Walker danced on the edge of being a cut above the wave of "hunks in hats" that took over the charts in the mid-90s, but ultimately rode a safe, commercial-friendly road to oblivion in the second half of the 90s.  But he still had some great songs in his early albums, including this first rate heartbreaker about a narrator who refuses to even accept that the love of his life has left him for good, always thinking she'll come home any day after leaving without saying goodbye.  "It's been a long, cold December....the snow outside keeps falling...I'll light a fire for when you come home".  Nothing like being a third-party watching a naive slug set himself up for a major league faceplant.

#9. Heart Half Empty--Ty Herndon and Stephanie Bentley (1995).....Most country music duets are uninspired affairs with powerhouse vocalists collaborating for a song with the quality of the song being more or less an afterthought.  One of the best exceptions to that trend came with two rookie artists who managed to find one of the best depressing country songs of the decade and giving  just the right level of vocal flare to a very cleverly written metaphor of a departing couple's bottle of wine that precedes their separation.  "Will your memories taste sweet as they linger....or the bitterness stay on my tongue....Is my heart half full of the love you gave me...or my heart half empty...because your love is gone".  Soul-crushingly depressing country songs rarely come with cooler lyrics than that.

#8. Whiskey Lullaby--Brad Paisley and Allison Krauss (2004).....One of the best country songs of the last decade would be amongst the top-five on any list of the darkest country songs of the last few decades, but also clearly works as a song to help suck the life out of anybody in a good mood.  My one grievance with this song is that the double suicide narrative seems a little melodramatic without context, but this song has one of the best videos ever made and the context necessary to make the song work is delivered in spades with the video.

#7. When You Think of Me--Mark Wills (2003)....I hesitated to include this song on the "merely depressing" list because it's emotionally charged enough to qualify for the "tearjerker" category, but thematically it comes closer to being a depressing song than the template for most bona fide tearjerkers.  The narrator tries to find the best way to "leave with dignity" without seeming like a complete asshole, but finds that easier said than done, ultimately walking away in the middle of the night while she sleeps and hoping she remembers the good times rather than his gutless departure.  It's almost as if he's written his "dear jill" letter in his mind with the lyrics "I think about the time I met you...I said I'd never forget you...and I won't."  Something tells me it's gonna be awhile till that pacifies her, and unlike most songs on the list you sympathize not with the narrator, but with the person on the receiving end.  Mark Wills gets a lot of perfectly fair criticism for gooey songs, but I found him to be pretty good at emotionally interpreting a good sad song, and never better than on this one.

#6. Matches--Sammy Kershaw (1998)......Here's a truly storybook country heartbreaker if there ever was one....the kind of song that could drag you down no matter how good of a mood you're in with haunting music and vocals along with masterful lyrics.  Very rarely has metaphorical allegory been employed as brilliantly as when the narrator uses the book of matches where he wrote the number down of the girl who would be the love of his life later gets employed to commit felony arson.  "Everybody at the Broken Spoke....they all thought my crazy story was a joke...now they're all out in the parking lot staring at the smoke".  Yikes!  Something tells me the narrator's clever fit of passion will be seen as a miscalculation when he's stepping into the prison shower in a few short months.

 #5. Till Summer Comes Around--Keith Urban (2009).....Since the dawn of the "redneck and proud" era of country music in the past decade or so, the depressing country song genre has taken it on the chin more than previous eras of my lifetime.  The one golden exception to the trend was this masterpiece by Keith Urban from five years ago.  Set to a genuinely haunting guitar backdrop, the narrator keeps returning to his lame summer job at the carnival year after year to rekindle the summer romance of the girl who "promised she'd be back again".  The narrative is entirely relateable as I did a less melodramatic variation on this gambit during my college years, with equally disastrous results.  But this narrator still hasn't gotten the hint that the love of his life won't be coming back although the final lyric hints that he finally sees the writing on the wall..."Baby I'll be back again....You whispered in my ear but now the winter wind is the only sound...and everything is closing down....Till summer comes around".  Keith Urban has been all over the map going back and forth between excellent songs and very mediocre songs, but it's a safe bet for me that he'll never top this....and that nobody in the current list of country artists is capable of a song this deliciously depressing.

#4. Still Losing You--Ronnie Milsap (1984).....I already established that Ronnie was a maestro at crafting the perfect sad country song and this was the most melancholy, slit-your-wrist depressor he ever recorded, or at least that he released as a single.  Set to an elaborate jazz-meets-rhythm-and-blues musical arrangement, the lyrics are stone cold country and Ronnie's vocals seal the deal with one of the most shamelessly moribund songs around, hitting one sad theme after another from the "fleeting memory in the image of your face" to the undeliverable phone call to the "party you have tried to reach has recently moved away" to my personal favorite "And so I paid my check and I buttoned my coat....Stepped into an evening rain...Made my way down the avenue....Softly whispering your name".  And best of all, the narrator was the one who initiated the break-up.  Dude, you screwed up big time!

#3. Broken Hearted Me--Anne Murray (1979).....I look at this as the first modern country heartbreak song.  Anne Murray built a name for herself in the 70s with mushy love ballads that seem too saccharine by the today's standards, where sentimentalism is ridiculed.  But the production polish she brought to those glossy, sappy ballads ultimately delivered in this gloomy love-gone-wrong ballad that has stood the test of time better than many of Murray's biggest hits of the late 70s.  The sweeping arrangement was quite unlike anything heard in country music before and can turn any smile into a heavy-hearted frown 35 years later.

#2. Everything That Glitters Is Not Gold--Dan Seals (1986).....The song that most music critics agree is the best song of Dan Seals' career almost serves as an anthology of every downer metric that can be pushed in a country song, with Dan Seals' vintage lyrical tricks on full display, giving the narrator false motivations early on only to reveal his true feelings.  In this case, the embittered narrator spews venom about the woman who left him and his young daughter while selfishly pursuing her rodeo queen dreams, but ultimately still can't get his love for her out of his head no matter much he resents himself for it.  Seals' vocal stylings on the choruses really take this song to the next level and no depressing since has depressed us so skillfully in the nearly three decades since.

#1. Blue Moon with a Heartache--Rosanne Cash (1982)....If there was only one depressing country song that I could listen to for the rest of my life, this would be the one.  Johnny Cash's daughter proved her artistic mettle on her breakthrough second album, and put together one of the darkest, droopiest, and most melancholy songs ever recorded, the kind of song Rosanne Cash excelled at in subsequent albums but never quite captured the dreary heartbroken funk of this song featuring lyrical gems such as "I'll play the victim for you honey...but not for free" and "what did I say to make your cold heart bleed this way...maybe I'll just go away today".  Even more than the lyrics, however, the musical arrangement seals the deal for this song, such a downer that you can practically feel your heart drop in your chest as it plays.  I suppose it's possible for another country song this depressing to be recorded again, but it could easily be another 32 years into the future before it happens.


Perhaps in the months ahead, I'll compile separate lists of country music's best tearjerkers and darkest songs and all categories have a number of songs worthy of acclaim, but for now I'm gonna revisit some of these classics again as they continue to fit my mood at this bleak juncture of winter 2014.

A Blogger Divided on Marijuana Legalization

Never will there come a time that there isn't a silly distraction for the peasantry to keep their minds off the fact that their livelihood is being stolen from them by an economy that rewards work and human capital less with each passing year.  The distraction du jour is the long-festering debate about marijuana legalization that has recently come to a head because of successful ballot initiatives in Colorado and Washington that legalized recreational use in those states.  A highly incomplete experiment on the merits of marijuana legalization is being conducted in these two petri dishes and for a number of reasons, I suspect the trend will catch on and a rising tide of legalization will ensue state by state in the decade to come.  How do I feel about this?  Suffice it to say my position is nuanced.

I've long had libertarian leanings when it comes to one's freedom to put whatever they choose into their bodies without persecution.  Ten years ago, I would have been firmly on the side of marijuana legalization.  But one pervasive trendline in the political realm over the last decade has led me to believe that a greater degree of persecution is likely to ensue against marijuana users in the aftermath of legalization than it does today.  But before I get into that argument, I don't think it's unreasonable to be libertarian on this yet still believe that legalization, and subsequent normalization and increased usage, of marijuana will be a scourge against society.  More intoxicated drivers on the highways, a less motivated workforce, and a larger number of young people already less well off financially than their parents and grandparents blowing thousands of dollars a year on pot are all inevitable consequences of increased marijuana usage.  And with more and more marijuana advocates loudly selling their drug of choice to the public as "completely harmless" or as "medicine", the lesser the social stigma will be when availability increases.  That strikes me a bad combination.

But what continues to trouble me most is my ongoing concern that marijuana legalization is poised to be another means for the political class to engage in reverse Robin Hood tax policy, with criminal justice implications ultimately going far beyond what marijuana users face today with the drug being quasi-illegal.  Colorado wasted no time imposing a 25% tax on the retail price of marijuana as it was legalized.  Now that's a bargain compared to a pack of cigarettes in the state of Minnesota where the combined state and federal tax now approaches 200% of retail, but it's also just an opening bid.  Every time the state is looking to plug a budget hole or to dole out money to a crony capitalist looking for a publicly funded sports stadium, you can expect to see an extra 0 added to that Colorado marijuana tax.  Simply put, legalized marijuana is an expansion of the litany of disproportionately working-class lifestyle choices that government views as a path-of-least-resistance means to extract revenue in the most regressive and predatory way possible.  And however bad it would get if Colorado was a stand-alone experiment, just wait until the feds start looking for their pound of flesh.

The naivete of the marijuana legalization advocates becomes most obvious when the topic turns to what legalized marijuana would look like if it went national.  Many of them seem to believe town squares full of hippies would be gathering to exchange homegrown marijuana to each other, not appreciating just how much government is gonna demand an ever-growing cut of the action in a nation where marijuana is legal.  The same phony argument of "externalized costs" associated with tobacco use will spread to marijuana, and all of the legislative supporters of legalization will instantly turn on it five minutes after it's legalized, blaming marijuana use on societal ills ranging from lower student test scores to growing obesity.  Not taxing this stuff through the nose will not be an option for lawmakers, and since tax collections will not be manageable through a mishmash of guys growing a dozen plants in their basements, government will seek to consolidate production and distribution of legalized marijuana by consolidating tax stamp authority into the hands of a few corporations, most likely the tobacco companies.  There is no major consumer item I'm aware of where production and distribution hasn't been consolidated by corporate America, and there is zero chance of marijuana being the exception to that.

Far as I can tell, the only reason marijuana wasn't legalized 25 years ago is that government recognizes that its multibillion-dollar annual profit-sharing racket with tobacco companies over cigarettes will be more logistically challenging to pull off with marijuana, simply because it's so easy for the aforementioned guy in his basement to grow his own marijuana than it is tobacco.  So what we're looking at a few years down the road, if current trendlines continue, is a junk corporate product chock full of cancer-causing chemicals being sold at stratospheric tax-inflated prices, but with a huge black market of pure homegrown product found in the basements of Joe Stoners across the country sold to a larger customer base of marijuana users than exists today at lower prices than what the government product sells for.  And this will undercut legalization advocates' argument that the criminal justice footprint related to marijuana today will shrink.  Anybody growing marijuana plants in their basement who undercuts the "sin tax" revenue bonanza that Uncle Sam fancies himself entitled to is gonna be squashed like a cockroach and made an example of.  If anything, I think more people will be going to prison for marijuana "crimes" five years after it's legalized than are today.

Most disheartening is that there's no reasoning with marijuana legalization advocates, as most of them are too giddy about the prospect of being able to legally get high on their drug of choice to entertain any dissenting voices.  They all but stick their fingers in their ears and say "la, la, la I can't hear you" when I outline what seems to be an inevitable and unsavory trajectory of legalization if it goes national.  It sickens me to see working-class America on the cusp of being taken advantage of in yet another way by government and corporate America yet it seems as though marijuana legalization is all but certain to become yet another means to accomplish that predatory end.  Ordinarily I would simply wish this issue would be resolved one way or another so we could move onto the economic stagnancy of the vast majority of Americans that is strangling the life out of the country, but I feel as though I have no choice but to chime in here since the outcome of this issue seems very likely to exacerbate the conditions of economic stagnancy and shift even more resources to the robber barons.

If I had any faith at all in legalization being done right I could grudgingly support this, but as the threshold of cynicism relating to legalized tobacco gets more shocking with each passing year, I have zero faith in legalization being done right.  Couple that with the fact that more pervasive use of marijuana will produce more tangible societal downsides than tobacco use and I find myself siding more with David Brooks than with doe-eyed marijuana legalization advocates whose arguments tend to be thinly guised 25-year-old talking points from the NORML website, failing to think more than one move ahead on what a nation of legalized marijuana will become.  My ultimate preference thus continues to be what it's been for a few years now......settle for marijuana decriminalization and quit while you're ahead, lessening the foolish criminal implications for those who use or sell marijuana while simultaneously keeping a lid on mainstream production and distribution, limiting usage and keeping government and corporations from getting their fingerprints on it.  As naive public opinion shifts more to legalization though, I'm less confident every day we can establish best practice here.