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The Best Depressing Break-Up Songs To Wallow In Your Own Self-Pity

Updated on February 23, 2013
Jeannieinabottle profile image

Jeannie has been writing online for over 8 years. She covers a wide variety of topics—anything from hamsters to office work.

They Say That Breaking Up Is Hard To Do...

Are you in the middle of a big break-up with your significant other? Are you tired of people trying to cheer you up? Maybe you want to wallow in self-pity for a while. You might even deserve to be a little depressed. Why can't people just let you feel sorry for yourself for a little while? Well, that is why I am here. I want to help you out by giving you some music that is perfect for your mood.

Break-up songs are a great tradition in music. Everyone likes at least a couple of break-up songs. Some break-up songs can even give you a sense of strength and empowerment! The songs on this music video list... not so much. This list is for break-up songs that really make you want to grab a box of Kleenex and sob along with the song. Welcome to the best depressing break-up songs so you can wallow in your own self-pity.

"Missing You" by John Waite

"Missing You" by John Waite is the perfect way to begin this depressing break-up song list. "Missing You" was a huge hit in the 80s and it's been remade by several artists. The reason why? It's awesome!

With lyrics like, "You don't know how desperate I've become and it looks like I'm losing this fight; In your world, I have no meaning," who wouldn't relate to this song? You can feel John Waite's pain pouring from the lyrics. The entire song is about how much he doesn't miss his ex, yet he ends it with, "I can lie to myself." Who hasn't been in denial about their true feelings to just to get through the day?

Missing You

"Nothing Compares 2 U" by Sinead O'Connor

Prince can sure write a great pop song, but he can also write an extremely depressing break-up song. "Nothing Compares 2 U" by Sinead O'Connor is one of Prince's masterpieces that he wrote, but Sinead made it famous.

The song is about trying to move on with life, but no one can ever compare to the ex. Sinead O'Connor sings this song full of remorse and pain. If her tears at the end of the video don't make you weep, too, you might have a heart of stone.

Nothing Compares 2 U

"It Must Have Been Love" by Roxette

Pop duo Roxette had a big hit with the super sad song, "It Must Have Been Love." With lyrics like, "It must have been love, but it's over now; It must have been good, but I lost it somehow," you are bound to be depressed and drowning in your own tears in no time. Not only is this song really depressing, it is a beautiful song as well.

It Must Have Been Love

"Back to December" by Taylor Swift

It is said nothing is worse than regret and that would certainly seem true if you listen to Taylor Swift's "Back to December." Taylor made the mistake of breaking up with someone she really loved and all she can do is go back in time. She remembers, "You gave me roses and I left them there to die," that paints a nice depressing image for her listeners. Taylor reflects on all her mistakes in this song. All she wants is a second chance, but we never find out if he will give her the opportunity. What a beautiful tear-jerker of a song!

Back to December

"How Am I Supposed to Live Without You" by Michael Bolton

How can we possibly have a depressing break-up song list without Michael Bolton? You simply can't, that is the answer! So let's all sit back and enjoy, "How Am I Supposed to Live Without You." This was originally recorded by Laura Branigan in 1983, but somehow Michael Bolton morphed this song into his own.

Poor Michael (and Laura) just can't figure out how they can live without the love of their lives. "How am I supposed to live without you when all that I've been living for is gone?" is the question posed in this song. If that isn't enough to get you crying, I don't know what will.

How Am I Supposed to Live Without You

"I Will Always Love You" by Dolly Parton

Some folks are more familiar with Whitney Houston's version of "I Will Always Love You," but Dolly Parton wrote this song and sang it best in my opinion. Dolly has recorded this song repeatedly and it is always a hit for her.

Basically, the song is about a couple that can't stand together. Dolly Parton wishes her ex joy and happiness without her. She knows they will no longer be a couple, but she will always love him. Now if that isn't depressing, I don't know what is.

I Will Always Love You

"Anytime" by Brian McKnight

I am going to be honest with you, this song gets me every time. I start tearing up before Brian McKnight even starts singing. "Anytime" is a song about lost love. With lyrics like, "Do I ever cross you mind... anytime?" and "Still have your picture in a frame, still hear your footstep down the hall," you are going to be crying along with this song in no time.

For anyone that ever ponders this question, the answer is always, "Yes!" Everyone always thinks about exes. Probably not everyday, but I know I wonder about ex-boyfriends and even former friends. So if you are sitting around wondering if your exes ever think about you, yes, they do. Brian McKnight, if you are out there, I guarantee you - you cross her mind!


"It's a Heartache" by Trick Pony

When you are compiling a list of depressing songs, you've just got to add, "It's a Heartache." Even though this song was originally recorded by Bonnie Tyler and then re-recorded by many other artists, I choose this version by the country band Trick Pony for this list.

Trick Pony decided it was not enough to sing a song called, "It's a Heartache." They decided to also create an extremely depressing music video for it as well. A sad break-up song plus a depressing music video equals the perfect addition to this music list.

It's a Heartache

"Breaking Up Is Hard To Do" by Neil Sedaka

OK, stop crying! Seriously, it is not so bad. You've had a really good cry now, so it is time to get over it. Trust me, you had your reasons. Chances are, you are way better off without that creep you were dating. So cheer up!

Here is a super fun break-up song by Neil Sedaka. Check out "Breaking Up Is Hard To Do" for an upbeat song about a break-up. There is no way you can be depressed about being single now. Remember, there are plenty of other people out there. Someone is bound to like you. If not, maybe you can buy a pet. As long as you feed it, it will love you no matter what. So stop sobbing and sniffling, and get back out there!

Breaking Up Is Hard To Do

Videos used in this hub are re-posted from YouTube.

All written material in this hub is by Jeannieinabottle.

Copyright ©2012 Jeannieinabottle


Submit a Comment
  • Jeannieinabottle profile imageAUTHOR

    Jeannie Marie 

    4 years ago from Baltimore, MD

    Thank you for the recommendation, Breanne.

  • Breanne Ginsburg profile image

    Breanne Ginsburg 

    4 years ago

    Another good song is "Carnivore" by Jewel.

  • Jeannieinabottle profile imageAUTHOR

    Jeannie Marie 

    7 years ago from Baltimore, MD

    Ardie - Hahaha... yes, some days a good sob fest is just the best thing to do. You don't even have to be breaking up with anyone. Thanks for visiting my hub!

    Alecia - Sometimes a sad song is necessary. However, sometimes a happy break up song is a good idea, too. Kelly Clarkson can sometimes be good for that. :-) Thanks for the comment!

  • Alecia Murphy profile image

    Alecia Murphy 

    7 years ago from Wilmington, North Carolina

    I love many of these songs so much. I don't have heartbreak anxiety but something about a really good sad song that makes you get through anything.

    I really like the Roxette song because it reminds of Pretty Woman.

    And Sinead actually got famous for covering Prince's ditty but it's so serenely heartbreaking it gets me every time. Great hub Jeannie!

  • Ardie profile image


    7 years ago from Neverland

    Im not even in the middle of a breakup but now Im sad too! I will admit there are days I am in a BAD mood and I just go with it. I pull out the sad songs and have a sob-fest or I put on some death metal and scream hahah Good Hub Jeannie

  • Jeannieinabottle profile imageAUTHOR

    Jeannie Marie 

    7 years ago from Baltimore, MD

    I don't blame you! Dating and break-ups just are not worth it after a while. Sigh. At least some good music has come from it all. You are right, too. These are great drinking songs. Thanks for checking out my hub and thanks for the votes!

  • robie2 profile image

    Roberta Kyle 

    7 years ago from Central New Jersey

    Been a long time since I had a break up or any reason for one-- I hung up the gloves and stopped the boxing match over a decade ago, but I still remember the tears and sadness that went with most of the songs on this great break up list. I'd also call these fabulous drinking songs as on Poor me, poor me pour me a drink. Nice job and a real trip down memory lane --voted up and interesting

  • Jeannieinabottle profile imageAUTHOR

    Jeannie Marie 

    7 years ago from Baltimore, MD

    Thomas, wipe away the tears and snot! You are just too awesome for that. I am happy you enjoyed the hub though. And yes, Whitesnake used to have some awesome break-up songs.

    Poetic Fool, there really is something to be said about wallowing in self-pity. It is annoying if it happens too much, but OK for a little while at least.

    epigramman, thanks so much! Thank you for sharing my hubs, too. Basically, I just love the song Missing You, and if you type that into YouTube, it suggests other depressing songs. I did come up with some of the last few without YouTube's help though.

    billbuc, thanks so much! Yes, sometimes I like to get depressed and rock out to these songs. Missing You is a great song for anytime though.

    Movie Master, yes, that is my favorite, too. Missing You is actually one of my all-time favorite songs. Every now and then, I need to wallow a bit. :-)

    Jamie Brock, thanks so much! Thanks for dropping by!

    Thanks everyone for the comments and joining me in the pity party!

  • Jamie Brock profile image

    Jamie Brock 

    7 years ago from Texas

    Nice list, Jeannie! Thank you for sharing :)

  • Movie Master profile image

    Movie Master 

    7 years ago from United Kingdom

    Some great tear jerkers here! a great list for self pity, I especially like Missing you, John Waite!

    Excellent hub and voted up!

  • billybuc profile image

    Bill Holland 

    7 years ago from Olympia, WA

    Great list! I do believe I have listened them a few over a thousand in my lifetime...sigh! Great job my friend!

  • epigramman profile image


    7 years ago

    ..left you a tasty comment at our music/group - lol - I would have posted this most excellent effort and world class homework assignment to the group myself if you had not beat me to it - I also intend to - right now - choose another terrific hub of yours and post and you will see what one it is - sending you warm wishes and good energy from lake erie time ontario canada 8:28pm and my love life is so bad that even the neighbor dogs are staying away from me

    p.s- and my choice for most depressing song or album is hands down - Berlin the album by Lou Reed - it also happens to be one of the most beautiful pieces of music I've ever heard ......

  • profile image

    Poetic Fool 

    7 years ago

    Been there, done that ... repeatedly! There is something insanely satisfying about wallowing in self pity. These are some great songs to wallow in! Fun hub!

  • ThoughtSandwiches profile image


    7 years ago from Reno, Nevada Ipod feels about ready to commit suicide. This is an impressive list of depressing songs. I seem to recall my 'list' had some heavy metal love ballads that were all flowing hair and screeching notes (White Snake comes to mind).

    Most excellent my friend...this list will wash away any sadness on a river of tears and snot...sometimes...that's how it has to be.



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