Top 10 Saddest Madonna Songs

1. Time Stood Still

   

   It's too bad Madonna didn't make this beautiful track a single. Nice lyrics.

2. Promise to Try

   

   One of the saddest songs I've ever heard in my life. I can't hear it without crying.

3. Oh Father

   

   This song is about freeing yourself from the pain, trauma, and abuse you experienced from a parent. It's about realizing that your parents weren't perfect and that perhaps they experienced abuse as well. It's a celebration of freedom from an oppressive household while also acknowledging that you understand why things might have been that way. It's not validating or justifying abuse but providing an explanation or reason for why it occurred. In many ways, this helps trauma survivors heal and move on from pain.

   Everyone who has lost their mom (assuming they were close, obviously) and was left with a dad who never really understood them can relate so deeply to this. Not having the support, and instead just having judgment from your dad when you've lost your mother, is like a poison to hope.

4. In This Life

   

   This song is about losing friends and family, and the world just not caring at all. Specifically, it addresses the AIDS crisis and how people turned a blind eye to the victims because they thought gay people deserved HIV/AIDS. Madonna is so raw and honest in this song - probably her most personal song to date.

   I love her performance of this song.

5. Paradise (Not for Me)

   

6. Something to Remember

   

   This song makes me so sad. It's about feeling like you're the right people but at the wrong time, like in another circumstance, things would've worked out. But in this life, it wasn't meant to be. Knowing this and being able to acknowledge the things you learned from this love - that's what the song details.

7. The Power of Good-Bye

   

   Cutting ties and saying goodbye is never a pleasant experience for most people, but leaving behind someone you love, for whatever reason, moving on and effectively ending a relationship forever is sad. What's incorrigibly devastating about it is the absolute finality of a proverbial goodbye.

   This song is about finally acknowledging and realizing that there's no salvation in what you had with someone, and learning to let go of them to reap the benefits of freedom.

   Quite possibly the most profound lyrics Madonna has ever written: "Freedom comes when you learn to let go. Creation comes when you learn to say No."

8. This Used to Be My Playground

   

   Wonderfully beautiful and touching song!

   This song is heartbreakingly nostalgic.

   I want this played at my funeral!

9. Mer Girl

   

10. Live to Tell

    

    Very interesting lyrics. It seems like people cannot trust themselves because there isn't much honesty in a divided society.

    Madonna's first sad song! Still one of the most memorable tracks from the '80s.

The Newcomers
11. ?

    Inside of Me

    
12. ?

    Pray for Spanish Eyes

    
The Contenders

13. Falling Free

    

    This song, it's hard to even explain what it's about. In ways, it's about freedom. It's an epiphany. It's letting go and releasing. Giving up, but for the sake of yourself. It's a sort of heartbreak in its final stages of acceptance.

    This one, for me, is about letting go when feeling overwhelmed. However, it's probably about her being more flexible and letting her guard down around someone whom she loves but doesn't trust.

14. X-Static Process

    

    This song completely caught me off guard when I first heard it. It's a wonderful, simple song. Madonna sounds great, and the lyrics were exactly what I needed when I found the song.

    This one hits hard when you know how it feels to be belittled and hurt by someone you idolize, like a parent, for example.

    I even cried while listening to it. Amazing song.

15. Gone

    

    The melancholic sound in this one is strong. The ongoing guitar rhythm, combined with her soft, pure voice and futuristic sounds, creates a magical feeling.

    Great performance, plus very touching lyrics.

16. Take a Bow

    

    This song is a thousand times sadder than Live to Tell and over a hundred times sadder than The Power of Good-Bye.

17. Frozen

    

    A beautiful ballad about having that one dear person in your life who's hurting others and themselves, but simply can't be helped by you. The video makes it feel even sadder than it really is.

18. Drowned World / Substitute for Love

    

    The melody of this one is mellow and somewhat sad. It's a sonic experience, as the message and lyrics radiate unstoppable hope.

19. Bad Girl

    

    This song is about feeling guilty and shameful for not being able to give what your partner deserves from a relationship. You love them, but you still need to work on yourself, and it hurts you to know that you're hurting them in the process.

    Its musical arrangement is marvelous. Bad Girl is one of my most favorite Madonna songs.

    It's like a story of a girl lamenting the realization that she'll never be able to force herself to be better. Being bad is all she knows, despite longing profoundly to be good.

20. Wash All Over Me

    

    The song, which somehow glorifies giving up, is particularly devastating when it comes from someone I've never expected to give up. On the other hand, there is some inexplicable solace both in the melody and the metaphorical freedom of letting go, characterizing the song.

    A recognition of being unable to fight and letting the metaphorical raging river carry you. The song sounds like it's finding solace and peace in helplessness, and is therefore confusingly devastating and hopeful simultaneously.

21. Best Friend

    

    As someone who's lost a best friend, a man I thought was my soul mate, I relate so heavily to this song. To feel like you tried everything to salvage something that was once a diamond and is now dust.

22. You'll See

    

    This song is about independence and rising above all struggles and challenges. It's about self-love and being strong enough to lift yourself from despair. It's about telling your detractors, You'll see me succeed someday.

23. You Must Love Me

    

24. To Have and Not to Hold

    

    This song is about when you love someone so much, but you know deep inside that things won't work out. You know you have to eventually let go, but it's hard because this person practically owns your heart, and yet they neglect you.

25. Devil Wouldn't Recognize You

    

    It feels like it's about being the only one who can defeat someone or something, yet at the same time, choosing to lose to them. It's kind of like fighting depression.

26. Sorry

    

27. I Deserve It

    

    Can't believe this one hasn't been mentioned!