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List of the Saddest Songs About Being Depressed

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I am a 35-year-old practicing attorney who writes about everything from pop culture to law.


Brief Introduction to my List

As Eminem said in Stan, "I can relate to what you're saying in your songs so when I have a sh1tty day, I drift away and put it on." Like many of you, I've found music helps me through tough times.

Maybe some of you readers out there will get some use and/or "enjoyment" out of it (i.e., listen to some of the songs in a murky swamp of self-pity), and I'll benefit by having a handy reference list for such times.

Anyway, I'll close with a quote. Was it Dick Van Patten, Kierkegaard, or Kid Rock who once said:

"Ain't no sunshine when you're low, I'm low; people tell me life's a game, I'm not playing. ... I have taken my blows but I'm still standing."

Gary Jules - Mad World

This is the one song to make my list twice, as Gary Jules' version of Mad World is perhaps more appropriate in tone than the original version by Tears For Fears (however, to me, Tears For Fears' version is superior because the upbeat tone contrasted to the lyrics creates a sense of disillusionment).

This Version Reminds me of Donnie Darko

Tears For Fears - Mad World

Here is the Tears For Fears version (pre-dating Gary Jules' version by about two decades). I like both versions, but I prefer this one. Which do you prefer?

This version confuses the sh1t out of many, but I prefer it.

Freddy Johnston - Bad Reputation

As is often the case, hearing this song in the context of a movie scene that matches content perfectly with a song's tone in the classic comedy Kingpin landed this song on my list.

Bob Dylan & Johnny Cash - Girl From the North Country

This is one of my all-time favorite songs, yet I've never been able to decide whether it is a love song, a song about loss, or both. Continuing the theme from the previous two entries, for this entry I am going to link to the song from a movie, Silver Linings Playbook, because I felt that the placement of the song was perfect for this scene.

Tom Jones - Delilah

This song was also used in a great movie scene (where "Irv" and Carmine Polito sung it together in an Italian restaurant in American Hustle), but as great as that scene is, it was happier than the song. Placing a label on this one is easy, it is about loss and, like Eminem many years later, killing a former lover. Hopefully such songs remain metaphorical, no matter what you've been through!

Nine Inch Nails / Trent Reznor - Hurt

Not much to be said about this one, but it is about as obvious an entry on this list as it gets.

NIN's Hurt Live

Radiohead - Creep and Street Spirit

I almost didn't include this one on the list because it is so obvious and that opens me up to attacks from the "interwebs." But you know what? Right now I'm kind of depressed anyway so fire away people; nothing you do to make fun of my list can make things any harder on me right now! Don't worry, I'm only kidding. Kind of. Not really. Whatever. Onto the next entry!

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I went with Street Spirit from The Bends but there are a ton of choices on this album. I could have instead chosen My Iron Lung, The Bends, Fake Plastic Trees or High and Dry. I love this album!

Jeff Buckley - Last Goodbye

Hopefully, through this less obvious entry, I'll be redeeming myself after selling my soul by taking the "low-hanging fruit" and putting Radiohead's Creep on this list.

You might recognize this song from the movie Vanilla Sky starring Tom Cruise. Good flick; great song.

Eminem - Rock Bottom and Stan

I have a love-hate relationship with Marshal Mathers. On the one hand, he creates some amazing songs near and dear to my heart, like Rock Bottom and, perhaps more well-known, Stan (feat. Dido). On the other hand, it was very difficult for me to forgive him for some of his inexplicably-most-popular offerings, such as The Real Slim Shady (or whatever that atrocity was called) and some of the other stuff from around that time. Thankfully, Mr. Mathers kind of redeemed himself with the album I picked up a few years ago, Recovery.

Oh, please beware, these songs are obviously NOT safe for work (or "NSFW," as I'm told the kids say these days).

Finally, I'd like to note that while Kim is definitely one of my all-time favorite songs, in the interests of appearing like less of a psychopath, I'm not going to include it on this list. If you know the song, or care to go investigate, you'll understand why.

Arthur Lee - Always See Your Face (Performed by Love)

One of my all-time favorite movies is High Fidelity starring John Cusack (this should come as no surprise, dear reader, as this movie is a kind of depressing-at-times movie about breaking up and reliving past failed relationships).

Anyway, the soundtrack to this epic movie is also stellar. Naturally, given what this movie is about, the soundtrack is replete with somewhat sad / depressing tunes and/or songs about breaking up.

Bob Dylan - Most of the Time

This gem from Bob Dylan is also on the High Fidelity soundtrack. Perfect for miring in self-pity after a breakup.

Bruce Springsteen - The River, Hungry Heart, Incident on 57th Street and 4th of July, Asbury Park

I'm a huge fan of the boss. For the third time, an entry on this list can be found on the High Fidelity soundtrack (i.e., The River). In fact, the Boss himself actually makes a brief cameo in the movie, giving sage relationship advice to John Cusack's character.

Hungry Heart almost didn't make this list, because it seems almost upbeat to me; specifically, I feel that the fella who's "got a wife and kid in Baltimore, Jack" and "went out for a ride and never went back" has kind of escaped a difficult situation (having a family and kids, etc.) Just kidding. But really, that stuff is no cakewalk. But complaining about it is lame. Damn you, Boss!

Incident on 57th Street is epic and I've always felt it is somewhat of an overall sad song, whereas Sandy is unquestionably about love lost; to wit: "Sandy, that waitress I was seeing lost her desire for me; I spoke with her last night - she said she won't light herself on fire for me anymore."

I don't know about you out there, but for me, there's nothing sadder than when a woman who previously loved me is no longer willing to self-immolate at my beck and call.

Jimmy Cliff - Many Rivers to Cross

Oh boy, I'm feeling really cheap again! That's because as I was getting ready to post this entry, I realized that this song is also on the High Fidelity soundtrack. But I promise I didn't just cut-and-past the soundtrack to create my own list. As mentioned previously, the movie is about relationship problems, loss, breaking up, etc., and they really nailed the soundtrack.

The Clash - Straight to Hell

I did it! After a few entries in a row that were all on the same killer movie soundtrack, I am posting one that isn't, and it is perhaps my favorite song on this list!

What is there to say about The Clash's classic Straight to Hell? Well, the only thing of any interest about this song other than its sheer greatness is that this song's riff was lifted by MIA and used as the background riff for her hugely popular Paper Planes.

Clarence Carter - Slip Away

If you've seen the movie Almost Famous, this classic from Clarence Carter is on the soundtrack, but you may have missed it. That's because it is kind of low and in the background during a scene with heavy dialogue and background noise (where the band is playing cards and the lead singer "trades" the groupie for a 6-pack, or something like that).

I thought that was a pretty good movie, and I love this song. I can't really put my finger on the reason I feel that this song is "sad" or about "loss," as in a way it is almost a love song. But I've always felt that it was kind of about loss and having moved on to different stations in life, and begging a past partner to ditch the husband and kids for a few hours and "bump uglies," which is sad for everyone involved, except, I suppose, for the person in Clarence's shoes.

Santo and Johnny - Sleepwalk

Okay, even though this one doesn't have any words, the rhythm and lead guitars are clearly crying, no?

Also, if you've ever seen the movie La Bamba, this song is playing whenever Richie has nightmares about planes crashing, and after he dies in a plane crash (I feel particularly bad for "Bob," Richie's brother who has always been kind of a total screw up, when he rushes home to be with his mother after the news of the crash is broadcast over the radio and she shrieks "NOT MY RICHIE!" I mean, the entire family is grieving so I'm not trying to criticize her as though she carefully selected her words, but I've always felt that it was implied that the mother felt that if she had to lose one of her sons, she'd rather it have been poor old "Bob" rather than Richie, the golden child; poor Bob!)

And for the first time ever, I've articulated, in writing, that one of the reasons I love this movie is that I identify with "Bob," the screw-up brother of Richie Valens (does this count as a "breakthrough" or something?)

Kid Rock - Black Chick, White Guy

This song is kind of ... um, epic, really. Some have said Kid Rock walked the line (or was flat-out racist) because he does drop an "N-bomb" in this song. That said, I don't feel that way, not when listening to the song and in context. Instead, I kind of see him as using the word in the same way a black person would (which is also not really appropriate and arguably racist, anyway, but my point is that I think those who have a gripe with him over this are, at a minimum, misguided, to the extent that they claim he's actually a racist).

This song is also ridiculously specific to one man's particular situation and circumstances, but not too hard to fit it into a comparison to your own situation when you're in a funk (at such times, everything is, of course, all about you, and all sad songs were written after being inspired by your relationship problems; amazing!)

Beatles - Let it Be

This one is perhaps another obvious entry onto this list. To my knowledge, it is about the singer losing his mother (by the way, look how cool and counter-cultural I am, as the name of the member of the Beatles singing this song escapes me; I'm so different a cool! Right? Anyone?)

Anyway, this song is sad to begin with. And then there's the context: this song was playing during one of the saddest moments of my life (I'll keep the specifics close to the vest, thank you, but it was an excruciatingly painful moment for me).

James Taylor - Fire and Rain

"I've seen lonely times when I could not find a friend."

Enough said.

Eric Clapton - Tears in Heaven

Saddest. Song. Ever.

This is about losing his very, very young son in a tragic accident (the little boy fell out of a window of his mother's apartment one morning; Eric arrived shortly thereafter to pick his son up. He was going to bring him to the zoo that day. After struggling to get "situated" as a father, Eric was finally becoming more comfortable and strengthening his relationship with his little boy. There are no words. I know it was a long, long time ago, but those wounds will never heal; I feel terrible for them.)

In case you, dear reader, don't know much beyond that this song is about Eric losing his son, instead of his stirring "Unplugged" performance, I linked a video with the song in the background that contains some of the backstory (to my knowledge, this is accurate, although I myself was only a young boy at the time of this tragic accident.)

N.E.R.D. - Sooner or Later

I like this song. It is pretty melancholy. It fits. Next!

Biggie (Notorious BIG) - Suicidal Thoughts and Everyday Struggle

I am perhaps the only attorney who can be spotted rolling into the Court parking lot listening to Biggie. It must look weird, especially for those familiar with my uber-respectful / traditional deferential demeanor before the Court, etc. Whatever, it is what makes me, me.

Anyway, I like both of these songs, but if you find out a friend or loved one is listening to Suicidal Thoughts, don't leave them by themselves. Seriously. I can't imagine listening to this song except for those times when I'm really struggling!

DJ Shadow's Remix - 6 Days

This song (or, more accurately, DJ Shadow's remix of this song) really does a good job capturing the feeling of ... desperation (?) I get from the lyrics, particularly "Tomorrow never comes until it's too late."

I've never seen any of the Fast and Furious movies, and I swear on my life that I will never watch any of them.

That having been said, this is apparently from the Tokyo Drift soundtrack. It was on my iPod, which was the most epic mix of songs ever. Thousands. All ill-gotten (i.e., free) from back when that was easy to do. Like a true jack-ass, I smashed it one day when I was really upset about one thing or another. Now it is gone forever (although I have thought a few times that maybe an Apple "Genius" or someone like that could perhaps fix it for me).

Anyway, I included this song on the list because it is perfect as a reminder to you when you're facing tough times that - as bad as today might seem - each and every day thereafter is only going to get harder and more difficult. So enjoy today's misery! (I suppose.) Whatever, I like listening to it when I'm struggling, even though I can't articulate why (as demonstrated by the first sentence in this paragraph.)

Audioslave - Doesn't Remind Me

"I walk the streets of Japan till I get lost, cause it doesn't remind me of anything."

"I [insert various different activities], cause it doesn't remind me of anything."

This song is clearly about appreciating things that help bring your mind off of everything that is weighing on you, and instead being "blissfully blank" (I just coined that phrase, so be sure to properly attribute it to DSmizzle if you ever use it.)

Kanye West - Homecoming and Heard 'Em Say (feat Adam Levine)

I'm not sure exactly why I think this belongs in this category. I've always felt that the lyrics of this song are kind of ... longing for the past? For instance "Now everybody got the game figured out all wrong, I guess you never know what you got till its gone; I guess that's why I'm here and I can't come back home."

Anyway, that's the vibe I get from this song so onto the list it goes!

Goodbye Yellowbrick Road - Elton John

This is clearly a song about moving on, whether from a relationship, changing a career path that didn't quite work out, or making another monumental change in your life, and it is clearly melancholy in its tone. By making such a decision, even if it is for the best, there will be a deep sense of loss felt.

All-time great song.

More to Come

Please note that this list is far from complete. If I were to sift through my memory for every song that belongs on this list from my entire lifetime, my brain having been bruised and battered by repeated concussive and sub-concussive impacts from high school and college football, I'd never finish it.

Anyway, please let me know what you think and drop me suggestions about songs you feel should be on this list. As I'm wrapping this paragraph up, I am already realizing some obvious classics I've omitted from this list, so I'll be updating it fairly regularly (unless I get depressed and lazy or something).


Pabo99 on January 18, 2018:

There are two songs that I’d add to the list:

Beirut - The Rip Tide.

Portishead - The Rip.


DSmizzle (author) from Long Beach, New York on February 11, 2015:

Thanks Minnetonka Twin! Glad we connected and I'm looking forward to checking out your material.

Linda Rogers from Minnesota on February 11, 2015:

I love your list of songs. Sorry to hear your going through a rough patch. I'm going through a financial crisis, so I can relate. I love the 'tears for fears' song you chose. I have tons of their CD's from back in the day. I'll send positive vibes and say a prayer that your rough patch will be an opportunity to open a door for you and make you stronger. Blessings :)

DSmizzle (author) from Long Beach, New York on June 10, 2014:

Off to Jackson, Mississippi, to get my head straight. Will hopefully be back in about 3 months. "Bye! Thanks for stopping by!"

DSmizzle (author) from Long Beach, New York on June 08, 2014:

Hi Aleen, thanks for reading and the new song recommendation, I'll definitely check it out.

Aleen on June 08, 2014:

Hey, so there's this one song that doesn't really have words to it, but has a sort of melancholic feel that longs for calm summer afternoons. It's called "Green Arrow" By: Yo La Tengo.

By the way, great list ya got here! I knew a lot of these songs, but some of them were new to me so thank you!

DSmizzle (author) from Long Beach, New York on June 07, 2014:

Thanks DC, I have to accept that I only have control over a limited number of the things going on around me and not to worry so much about the other stuff. I am still waiting for my first night of sleep in the past 7 days to last more than 3-4 hours.

DowntroddenInDC from Houston, TX on June 07, 2014:

Nice list. Hope you get out of that 'rough patch' soon!

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