Top 10 Saddest Madonna Songs

The Top Ten
1 Promise to Try

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

2 Oh Father

This song is about freeing yourself from the pain, trauma and abuse you experienced from a parent. It's about coming to the realization that your parents weren't perfect, and 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've been that way. It's not validating or justifying abuse, but giving it an explanation or reason as to why it occurred. In many ways, this helps trauma survivors heal and move on from pain

3 In This Life

This is about losing friends and family, and the world just not caring at all. Specifically this 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.

4 Paradise (Not for Me)
5 The Power of Good-Bye

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

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

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."

6 This Used to Be My Playground

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

I want this played at my funeral!

7 Something to Remember

This song makes me so sad. It's about feeling like y'all are 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.

8 Mer Girl
9 Live to Tell

Very interesting lyrics. It seems like people can not trust themselves because there is not much honesty in a divided society.

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

10 Falling Free

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

The Contenders
11 Time Stood Still

Too bad Madonna didn't make this beautiful track a single. Nice lyrics

12 Frozen

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

13 Drowned World / Substitute for Love

The melody of this one is somehow mellow and kind-of-sad. It's just the sonical experience here, as the message and the lyrics are radiating with unstopabble hope.

14 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 arrangements is marvelous. 'Bad Girl' is one of my most favorite Madonna songs

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

15 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 belitelled and hurt by someone you idolise. Like a parent for example.

I even cried while listening to it. Amazing song

16 Gone

The melancholic sound on this one is strong. The ongoing guitar rhythm with her soft pure voice. The futuristic sounds create a magical feeling.

17 Take a Bow

This song is a 1000 x times sadder than Live To Tell and over 100 times sadder than The Power of Goodbye.

18 You'll See

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

19 You Must Love Me
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 unexplicable solace both in melody and the metaphorical freedom of letting go, characterising the song

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

21 To Have and Not to Hold

This 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.

22 Devil Wouldn't Recognize You

Feels like it's about being the only one who can defeat someone, or something, yet at the same time keep chosing to lose from them. Kind of like fighting depression.

23 Sorry
24 I Deserve It

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

25 Forbidden Love

A reminder that sometimes we simply don't get fo have even something as beneficial & harmless as love. But then, we may get anothet kind of love, or a sbstitute for it, which is eve better. Love the slow, peaceful and sort of resigning melody

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