Saddest Madonna Songs

The Top Ten Saddest Madonna Songs

1 The Power of Good-Bye

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

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."

Nice song

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

3 This Used to Be My Playground

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

4 Oh Father

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

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.

5 Paradise (Not for Me)

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

I love her performance of this song

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

8 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

9 Wash All Over Me

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

10 Mer Girl

This song makes me want to run from life

The Contenders

11 Time Stood Still

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

12 Frozen

At least in top 10

13 Bad Girl

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

14 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.

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.

I even cried while listening to it. Amazing song

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

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

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🥺

23 Ray of Light
24 Falling Free
25 Love Tried to Welcome Me
26 Best Friend
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