Saddest Madonna Songs

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

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

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

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

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.

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

I love her performance of this song

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

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

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

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

At least in top 10

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

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

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

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

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