Saddest Hip Hop Songs


The Top TenXW

1Stan - Eminem

This might be the most obvious #1 in this whole website. No joke this is really emotional and I think it is the 2nd best song Eminem has ever written. And a shout out to No Love. I think that should be right up here with Stan.

Damn, he's irreplaceable. Best of the best! Speechless about lyrics, speechless about his manner of rapping, about his talent. May God bless and keep you, 'cause Em, you're the one!

This Truely Deserves number 1 spot for the Saddest Rap Songs Ever...
P. S
When I'm Gone, Like Toy Soldiers, Mockingbird ^^ No Love Should be in The Top 10 List...
When I'm Gone made my Aunt Cry...

Anytime Eminem uses his Marshall Mathers persona, it's usually sad - KrazzyMadd

V21 Comments
2I'll Be Missing You - Puff Daddy

So emotional, especially to anybody that has lost someone that they truly love. This is also Puff Daddy's most popular song

This song is really sad when you understand the true meaning of it... After you have lost someone that you truly love.

Great song. This song is way sadder than Stan. Stan is about a made up character but this song came from the death of notorious big one of Puff Daddy's best friends

Better than Stan

V8 Comments
3Dance With the Devil - Immortal Technique

This song shocked me when I first heard it, a guy who killed his own mother and then committed suicide. It's so deep.

It makes my cry every time, this has happened to so many little thugs that want be a gangster

This song is phenomenal. The first time time you hear it, it just leaves there thinking. Maybe you are shocked that is why, at the begining, you think like "Wow, this terrifying! ", but then you start to grasp the message conveyed through the song and you appreciate it.

Stan is nowhere near to it you ass prejudiced guys, I love marshall I love Eminem but dance with the devil is hands down more sad then stan for life. Stan was good... but IMMORTAL really took the spot this time.

V15 Comments
4Dance - Nas

This song will always mean so much to me! I do have a mother but I can only imagine the pain and nas made this song so good!

"makes me think about how long I got my mother and what I couldve done to make her life easier "

Damn, when I heard this song I was speech less. I recently lost a person I loved and this song opend me up.

Such deep meaning to the song!

V2 Comments
5When I'm Gone - Eminem

The first hip-hop song to make me cry.. Even my mom cried

"Now go out there and show em' that you love em' more than us"... Enough said.

Truly one of Eminem's greatest. It is true-All the fame and wealth means nothing without one's family. Even the video's heartrending.

One of the saddest song by the rap god. The lyrics are so great.

V8 Comments
6Brenda's Got a Baby - 2Pac

2pac-based on a true story-real life.

More than twenty years old, and I'm still shocked... It's on the greatest hits album but most times I skip it because I can't take it...

It's on the greatest, most honest song ever. We all know some Brenda.

This songs make me cry

V2 Comments
7Dear Mama - 2pac

Dear mama should be number 1 why? Cause he expresses his feelings and appreciate his mother for all she done for him with honor #1 2Pac-Dear Mama

It's the most moving rap song of all time. Plain and simple. It is also one of the best rap songs of all time

This is list is by far wrong, this song should be here though.

It 2pac he pours his heart and soul into his music what else is there to say

V8 Comments
8Happy Birthday - Flipsyde

Song is touching. Abortion is just as mentally deteriorating for would've been fathers and it's great to hear a song from a would've been father's point of view. A really good song.

Not sure if I agree, but this comment does sound interesting but I can't stand rap music so I will probably never have the guts to type this song into YouTube and search for it and then listen to it. So sorry! - JamiePrice

Song about a man who paid for his baby mama's abortion and how much he regrets it.

most amazing & saddest song I've ever listened to :'(

So powerful when I listened to it!

V1 Comment
9Mockingbird - Eminem

All the longings of a separated father and a daughter more than justified. A beautiful rap, I remember my dad every time I listen to this. Its is partially applicable to my life.

This is one of the saddest songs of all time in my opinion.

I love this song it unlike most raps it has a lot of emotion in it

V4 Comments
10Changes - 2Pac

This song deserves to be number 1. 2pac has made a huge impact not just in hip hop, but in the world. Taking hip hop to a diferent level and make his words and thoughts reach other peoples lifes. 2pac, the greatest of all time.

Guys this isn't a 2pac forum. It's not even talking about which songs are the best, it's the saddest songs. Nothing to do with the quality of the song. Jeez, at least Eminem fans get their shut down fast. 2pac just flood the area and don't get told off

Super strong lyrics, very powerful

V1 Comment

The Contenders

11My Life - The Game

One of the tightest songs on here

V1 Comment
12Suicidal Thoughts - Notorious B.I.G.

Song about being depressed and is what it's a meant to be

It is a great song and it came great with the album

Song really relatable and it really helps me.

And as a matter of fact, I'm sick of talking. - Bboymakinwitthefrekfreak

V3 Comments
13Love the Way You Lie - Eminem

makes you feel depressed about your life.
Sad love story.

V4 Comments
14Like Toy Soldiers - EminemV3 Comments
15Runaway Love - Ludacris

I can't remove this song + brenda got a baby from playlist, this is what I always see in community.

I always can listen to this song and help me clear my head
It is so touching.

16Thank You - Xzibit
17Hail Mary - 2Pac

This is a great song and what not but how the hell is it sad?

V1 Comment
18Difficult - Eminem

Eminem uses all of his forces to make this ultimate tribute to his best friend, Proof. Matter of fact he isn't even Eminem in this song, he is Marshall Mathers.
Saddest song I've heard

Should be a little higher than #18 on this list. You could hear the true, fresh, raw pain coming out of Em in this track as he mourns the death of his best friend, Proof. R.I.P.

What? This is one of the saddest. Em can barely even make out some words. He puts so much emotion in this song, way more than some of his other songs. Great song dedicated to his best friend.R.I. P Proof.

Touching story of the lost of loved ones

V8 Comments
19Hey Mama - Kanye West

I thought this list was about sad songs, stan is good but I don't think it was ever meant to be a 'sad' song. Hey mama is about kanye's mother and after my mother passed away I can start to imagine what kanye went through after it happened. I know I might get a lot of hate for this but I like it better than dear mama, because I can relate to it more (i wasn't raised in the 'projects'). I listen to this song on her birthday every year and it's really sad. If Kanye west ever reads this, I want to thank you for putting this song out there, it really means a lot to me.

20Roses - Kanye West
PSearch List

Related Lists

Best Hip Hop Songs of All Time Top Ten Hip-Hop/Rap Songs Best Hip Hop & R&B Songs Top Hip Hop Songs of 08 Best Songs On Vh1's List of Best Hip Hop Songs

List StatsUpdated 24 Oct 2016

1,000 votes
133 listings
5 years, 348 days old

Top Remixes (8)

1. Dance - Nas
2. I'll Be Missing You - Puff Daddy
3. Mockingbird - Eminem
1. I'll Be Missing You - Puff Daddy
2. Dear Mama - 2pac
3. Hail Mary - 2Pac
1. Dear Mama - 2pac
2. Stan - Eminem
3. When I'm Gone - Eminem

View All 8


Add Post

Error Reporting

See a factual error in these listings? Report it here.