Saddest Madonna Songs


The Top Ten

1 The Power of Good-Bye

Nice song

The is the only Madonna song to make me cry

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." - theOpinionatedOne

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2 Promise to Try

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


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

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3 This Used to Be My Playground

Wonderfully beautiful and touching song! - Irina2932

This song is heartbreakingly nostalgic.

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4 Oh Father

Even her vocal sounds so great here. The song is moving - Irina2932

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.

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.

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5 Paradise (Not for Me)

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

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6 In This Life

I love her performance of this song - Irina2932

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7 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.

Great performance plus very touching lyrics - Irina2932

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8 Wash All Over Me

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

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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 - Irina2932

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10 Time Stood Still

Too bad Madonna didn't make this beautiful track a single. Nice lyrics - Irina2932

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The Contenders

11 Mer Girl UListen to Sample
12 Bad Girl

Its musical arrangements is marvelous. 'Bad Girl' is one of my most favorite Madonna songs - Irina2932

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13 Frozen

At least in top 10 - Brxtney

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14 X-Static Process

I even cried while listening to it. Amazing song - Irina2932

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15 Take a Bow UListen to Sample
16 Something to Remember UListen to Sample
17 Sorry UListen to Sample
18 Drowned World / Substitute for Love UListen to Sample
19 You'll See UListen to Sample
20 To Have and Not to Hold UListen to Sample
21 I Deserve It

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

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22 You Must Love Me

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

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23 Ray of Light UListen to Sample
24 Falling Free UListen to Sample
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Related Lists

Top 10 Madonna Songs Top Ten Most Iconic Madonna Songs Top 10 Madonna Songs That Should Have Been Released As a Single Most Badass Madonna Songs Most Underrated Madonna Songs

List Stats

100 votes
24 listings
5 years, 7 days old

Top Remixes

1. The Power of Good-Bye
2. Promise to Try
3. Paradise (Not for Me)
1. This Used to Be My Playground
2. Oh Father
3. Time Stood Still
1. This Used to Be My Playground
2. Frozen
3. Oh Father


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