Top 10 Saddest Madonna Songs

It's too bad Madonna didn't make this beautiful track a single. Nice lyrics.

One of the saddest songs I've ever heard in my life. I can't hear it without crying.

This song is about freeing yourself from the pain, trauma, and abuse you experienced from a parent. It's about realizing that your parents weren't perfect and that perhaps they experienced abuse as well. It's a celebration of freedom from an oppressive household while also acknowledging that you understand why things might have been that way. It's not validating or justifying abuse but providing an explanation or reason for why it occurred. In many ways, this helps trauma survivors heal and move on from pain.

This song is about losing friends and family, and the world just not caring at all. Specifically, it addresses the AIDS crisis and how people turned a blind eye to the victims because they thought gay people deserved HIV/AIDS. Madonna is so raw and honest in this song - probably her most personal song to date.

This song makes me so sad. It's about feeling like you're the right people but at the wrong time, like in another circumstance, things would've worked out. But in this life, it wasn't meant to be. Knowing this and being able to acknowledge the things you learned from this love - that's what the song details.

Cutting ties and saying goodbye is never a pleasant experience for most people, but leaving behind someone you love, for whatever reason, moving on and effectively ending a relationship forever is sad. What's incorrigibly devastating about it is the absolute finality of a proverbial goodbye.

This song is about finally acknowledging and realizing that there's no salvation in what you had with someone, and learning to let go of them to reap the benefits of freedom.

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."

Wonderfully beautiful and touching song!

This song is heartbreakingly nostalgic.

I want this played at my funeral!

It feels like it's about being the only one who can defeat someone or something, yet at the same time, choosing to lose to them. It's kind of like fighting depression.

This song, it's hard to even explain what it's about. In ways, it's about freedom. It's an epiphany. It's letting go and releasing. Giving up, but for the sake of yourself. It's a sort of heartbreak in its final stages of acceptance.

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.

A beautiful ballad about having that one dear person in your life who's hurting others and themselves, but simply can't be helped by you. The video makes it feel even sadder than it really is.

The melody of this one is mellow and somewhat sad. It's a sonic experience, as the message and lyrics radiate unstoppable hope.

This song is about feeling guilty and shameful for not being able to give what your partner deserves from a relationship. You love them, but you still need to work on yourself, and it hurts you to know that you're hurting them in the process.

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

It's like a story of a girl lamenting the realization that she'll never be able to force herself to be better. Being bad is all she knows, despite longing profoundly to be good.

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 belittled and hurt by someone you idolize, like a parent, for example.

I even cried while listening to it. Amazing song.

The melancholic sound in this one is strong. The ongoing guitar rhythm, combined with her soft, pure voice and futuristic sounds, creates a magical feeling.

This song is a thousand times sadder than Live to Tell and over a hundred times sadder than The Power of Good-Bye.

This song is about independence and rising above all struggles and challenges. It's about self-love and being strong enough to lift yourself from despair. It's about telling your detractors, You'll see me succeed someday.

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 inexplicable solace both in the melody and the metaphorical freedom of letting go, characterizing the song.

A recognition of being unable to fight and letting the metaphorical raging river carry you. The song sounds like it's finding solace and peace in helplessness, and is therefore confusingly devastating and hopeful simultaneously.

This song is about when you love someone so much, but you know deep inside that things won't work out. You know you have to eventually let go, but it's hard because this person practically owns your heart, and yet they neglect you.

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

A reminder that sometimes we simply don't get to have even something as beneficial and harmless as love. But then, we may get another kind of love, or a substitute for it, which is even better. I love the slow, peaceful, and somewhat resigning melody.