Saddest Eminem Songs

The Top Ten
1 When I'm Gone

Always singing about his family and how much he loves them. What music should really be about.

This song makes me cry a little bit. This is a good song.

The saddest song, but the most loved song I listen to.

2 Stan

The best storytelling in a song ever.

3 Mockingbird

This is literally one of the saddest songs by Eminem. He talks to his daughter about his life, mostly before fame, and how much he tries to be a good father. It almost made me cry.

This is the saddest song Eminem ever made. How in the world Stan is above Mockingbird, I don't know, but this is the saddest song.

How is Stan above Mockingbird? When I first listened to Stan, I didn't cry but when I heard Mockingbird, good lord I was sobbing.

4 Difficult

If everyone knew and actually listened to this song before, it would definitely be #1. This song is about his best friend from childhood who died. I just listened to it too lol but before I listened to it I thought that there was no way that this song could be sadder than Mockingbird, but I was wrong.

This is the saddest song Eminem ever wrote. It wasn't even meant to be released. It shows that Em did this for himself and that he actually uses music as a release.

Unlike When I'm Gone, this song has no happy ending. It's just pure devastation. Most people never heard it because it's an unreleased track, but it can be found on Bad Meets Evil: The Shady Project. The song is about Proof's death. R.I.P. Big Proof.

5 Beautiful

To me, this song is rather underrated on this list. Perhaps it's because I can relate to it more than almost any of Em's songs. Yes, Rock Bottom is great too, almost as much as When I'm Gone.

This should be number one, or at least When I'm Gone. You could really feel his emotion in this song.

So sad. The first line says it all.

6 Like Toy Soldiers

The music video made me tear up. That's progress because I never cry! How is this number seven?

The most underrated Eminem song!

This song has a great meaning. It's about Proof's death and the events that led to it.

7 Cleanin' Out My Closet
8 Rock Bottom

This song tops Stan in sadness because you feel this is what Marshall actually went through. At least in my opinion.

This is one of the most devastating rap songs of all time. Eminem sounds hopeless about money troubles.

9 Lose Yourself
10 Headlights

I thought that Eminem would never say that he was sorry to Debbie Mathers (he even said her name and felt guilty after all of the shade he threw at her), but I spoke too soon. I literally cried the first time I listened to this.

I truly love this song! This song actually has a purpose instead of being a stupid song. The song is about an apology to his mom (*cough* Cleaning Out My Closet *cough*).

None of the songs above are even close to how sad this song is. None of the ones above made me cry. This one did.

The Newcomers

? Somebody Save Me
The Contenders
11 Going Through Changes

I cannot believe that this song is in 12th place on this list. It is literally one of the saddest things he has written. The music, the emotion, the delivery, and the melancholy you can hear in his voice are almost incomparable to any other song he has released.

He talks about what he has been through, the changes he went through, and the impact of fame on his personal life and relationships with his friends, daughter, and ex-wife. It is a story that would make anyone with a tiny bit of emotion tear up or sit for a moment and think.

12 Space Bound

I can't in any way relate to this song, but it makes me cry. It's so sad.

This song should be higher on the list.

13 Arose

This song describes what would have happened if he had stuck to drugs. But he makes an amazing comeback in the last verse, which is a real-written version of the previous track's last verse, "Castle."

This song made me cry so many times! Something that separates Em from most artists is his willingness to sink into a dark and painful place within himself so the emotion is raw.

This song makes me feel things. The words hit me and make me cry.

14 The Way I Am

Be honest, when someone is willing to accept that whatever you say he is, is what he is, it must mean they are totally beaten down. The meaning behind this song passes over the head of most listeners.

15 Hailie's Song

I feel like this is one of his most genuine songs that he's ever made.

16 No Apologies
17 Love the Way You Lie

Ok, how is this so low? Have you seen the video? Yeah, When I'm Gone is sad, but I never cried with Mockingbird, and that's number 3. This is such a sad song that I wonder why it's so low down. It used to always make me cry.

This is so sad. Why is Mockingbird higher? This song is one of the saddest songs I've ever heard.

18 Sing for the Moment
19 Kim

Actually insanely depressing. Look up the lyrics.

Great sad song for those who experience sadness and anger simultaneously.

20 You're Never Over

Honest talk, brutal if you understand the words.

21 Fack

So beautiful. It talks about depression, pure emotion, financial difficulties, substance difficulties, his daughter Hailie, and everything of the above. It definitely doesn't talk about sex fetishes and shoving gerbils up one another's ass, just no. It's such a beautiful song and should be number 1. Who here agrees with me?

This is so damn beautiful. Put Stan and When I'm Gone together and you wouldn't be able to top this masterpiece. 10/10. Em, I'm in tears.

The most brutally heartbreaking song that I've heard in years.

22 Legacy

"I had a bad day at school, so I ain't talking..." I always listen to this song after a bad day at school or just a bad day in general.

23 Deja Vu
24 Stronger Than I Was

This sympathetic song provides insight into Eminem's relationship with ex-wife Kim and how he apologizes for acting how he did towards her, particularly on The Marshall Mathers LP 1. It's the polar opposite of the track "Kim" from the original MMLP.

25 No Love
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