Top 10 Saddest Madonna Songs

The Top Ten
1 Promise to Try Promise to Try Cover Art
2 Oh Father Oh Father Cover Art

Everyone who had lost their mom (assuming they were close obvi), 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 of your dad when you have lost your mother is like a poison to hope.

The saddest of all, definitely. The lyrics in the end: "You didn't mean to be cruel
Somebody hurt you too" and the melody growing and growing until only unbearable sadness and pain remain.

Madonna's vocals on this song tear my heart apart. Those vocals with the growing melody right up untill the last part are like no other song she ever made.

The phrase "You didn't mean to be cruel, somebody hurt you too" just kill me... and the music telling you that she still feel the pain... it's beautiful sadness.

3 In This Life In This Life Cover Art
4 Paradise (Not for Me) Paradise (Not for Me) Cover Art

Looking to the past at her late mother and seeing herself carried into the future through her daughter..it's a strange and powerful juxtaposition

5 The Power of Good-Bye The Power of Good-Bye Cover Art

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."

Believe it or not, this song by Madonna was released before the 9/11 attacks.

6 This Used to Be My Playground This Used to Be My Playground Cover Art

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

7 Something to Remember Something to Remember Cover Art
8 Mer Girl Mer Girl Cover Art
9 Live to Tell Live to Tell Cover Art

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 Frozen Frozen Cover Art

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.

At least in top 10

The Contenders
11 Time Stood Still Time Stood Still Cover Art

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

12 Falling Free Falling Free Cover Art

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.

13 Drowned World / Substitute for Love Drowned World / Substitute for Love Cover Art

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 Bad Girl Cover Art

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 :(

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

15 X-Static Process X-Static Process Cover Art

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 Gone Cover Art

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 Take a Bow Cover Art

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 You'll See Cover Art
19 Wash All Over Me Wash All Over Me Cover Art

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

20 You Must Love Me You Must Love Me Cover Art
21 Devil Wouldn't Recognize You Devil Wouldn't Recognize You Cover Art

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.

22 Sorry Sorry Cover Art
23 To Have and Not to Hold To Have and Not to Hold Cover Art
24 I Deserve It I Deserve It Cover Art

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

25 Forbidden Love Forbidden Love Cover Art

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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