Saddest Madonna Songs

The Top Ten
1 The Power of Good-Bye The Power of Good-Bye Cover Art

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.

The is the only Madonna song to make me cry

2 Promise to Try Promise to Try Cover Art

The most beautifulsong ie ever heard, it's about her mother dying

This is masterpiece,you can't listen it without cry

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

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

4 Oh Father Oh Father Cover Art

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.

Even her vocal sounds so great here. The song is moving

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.

5 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

6 In This Life In This Life Cover Art

I love her performance of this song

7 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.

Great performance plus very touching lyrics

8 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

9 Wash All Over Me Wash All Over Me Cover Art

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

This song always makes me cry,it reminds me of being late to see my mum at the bus station 😞

10 Mer Girl Mer Girl Cover Art

This song makes me want to run from life

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 Frozen Frozen Cover Art

At least in top 10

13 Bad Girl Bad Girl Cover Art

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

14 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.

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.

I even cried while listening to it. Amazing song

16 You'll See You'll See Cover Art
17 Something to Remember Something to Remember Cover Art
18 Drowned World / Substitute for Love Drowned World / Substitute for Love Cover Art
19 You Must Love Me You Must Love Me Cover Art

This is the ONLY thing that makes me cry. The fact that she is surprised that someone could love her through thick and thin🥺

20 Sorry Sorry Cover Art
21 To Have and Not to Hold To Have and Not to Hold Cover Art
22 I Deserve It I Deserve It Cover Art

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

23 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

24 Devil Wouldn't Recognize You Devil Wouldn't Recognize You Cover Art
25 Ray of Light Ray of Light Cover Art
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