Saddest Hip Hop Songs


The Top Ten

1 Stan - 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...

Deep, strong, once you understand the lyrics you'll never forget them.

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2 I'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


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3 Dance 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.


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4 Dance - Nas

Nas is a powerful artist, I have to hold back tears listening to this song. I still have my mother and it makes me wanna go give her a hug and a kiss on the cheek.

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 "

Such a sad song

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5 When 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.

Just take another pill yeah I bet oh you will you rap about it

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6 Brenda'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...

Shockingly real, and brilliantly effective on the listener, the video is equally sad.

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

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7 Dear 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.

Should be number 1 this song made everyone cry

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8 Happy 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!

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9 Mockingbird - 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.

Regret and no way back, no replay option. The saddest of the sad.

This song is one of the best

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10 Changes - 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

I cry when he said somethings Will never changes " Rest in peace makavelli the don my favorite rapper and song😊

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The Contenders

11 My Life - The Game

One of the tightest songs on here

Awesome chorus you can't just stop bieng emotional n' senty - Amshee

12 Suicidal Thoughts - Notorious B.I.G.

Ill and also sad story

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

Great piece, carrys such power.

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13 Like Toy Soldiers - Eminem

Eminem is telling a story, clear and direct story of events, but the chorus hits hard

My favorite of his songs. - letdot52

I thought Toy Soldiers was a diss track for ja

Toy soldiers is a diss track to Ja rule and benzino

14 Love the Way You Lie - Eminem

Love this song with passion

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

This isn't sad, just angry

Really good song #peter_angelov

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15 Runaway 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.

16 Thank You - Xzibit
17 Hail Mary - 2Pac

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

How is this sad?

18 Roses - Kanye West
19 Difficult - 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.

Honestly why is this 19, it shows a lot of true emotion form eminem, to be honest eminem isn't singing this song, Marshall Mathers is, super sad...

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20 Hey 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.

21 Heartless - Kanye West

Why don't you vote dis song...? That really deserves a lot...

Wow How could be so Dr. Evil, you bringin' out a side of me that I don't know
I decided we weren't going' speak so
Why we up three A.M. on the phone
Why does she be so mad at me for
Homie I don't know, she's hot and cold
I won't stop, I won't mess my groove up
Cause I already know how this thing go
You run and tell your friends that you're leaving me
They say that they don't see what you see in me
You wait a couple months then you gon' see
You'll never find nobody better than me

22 Lost Ones - J Cole

This song is so beautiful and touching, J Cole always has one of the best lyricists of his generation

This song is so beautiful and touching to the soul

Suppose to be number 2

This should be #1, so relatable

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23 Where'd You Go - Fort Minor

The music just sets a great tone for the lyrics. Pretty powerful stuff, and is somewhat timeless.

A song that just gets to you no matter what

Its just so touching!

Where'd you go
I miss you so
Seems it's like been forever
That you've been gone
Please come back home...

24 You Never Know - Immortal Technique

It's a beautiful, unconventional track about him falling in love with a girl. What makes it stand out from the usual love song is that he never engages with her sexually. Never makes a move or pushes her to do anything. It's refreshing to hear a track that isn't full to the gills with misogyny. It's a one of a kind song, immortal technique definitely knows how to make fire.

You need to go listen to this song it has so much emotion and a deep sad story this should be up in the top ten

Brings me back..immortal as always telling a story

Should definitely be on top of this list.
Immortal technique is a Great storyteller and its unbelieveable how he can make you focusse on The Lirycs for 8 Minuten or so.
Greets from Germany.
You Gotta a Hufe fanbase out Here.

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25 Sing About Me, I'm Dying of Thirst - Kendrick Lamar

This song is seriously sad, he wrote the lyrics in perspective of his best friend, and it's a true story..

Amazing, one of the best songs of all time in my opinion

This is unreal, in this song, he changes perspectives from keisha (a murdered prostitute), then the brother of his friend who got murdered, who got murdered himself, and finally to himself.


26 The Crossroads - Bone Thugs-N-harmony

Song is just full of emotions, just makes you think about life, didn't make em cry really but I wouldn't be shocked if it did, overall most beautiful hip hop song ever

This should be up there. This song is a masterpiece. It is very emotional

Should be the top ten one of the saddest songs ever

This song is really touching, specially if you lost some one you love deeply.

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27 Song Cry - Jay-Z

This song makes one wonder if Jay-Z is talking about a random b! Tch he met, or whether he's talking about his true love.. Should be Top 10.

This list is wack, what stan is not sad, its humorous! The saddest songs r missing u, dance, & a bunch of the other Eminem songs & this... Etc. Etc.

28 Kurt Kobain - Proof

This is almost like suicide note and its really sad. Its almost like he knew he was going to get shot.

What I really like about this track is that proof talks about two people here Kurt Cobain and Eminem.its true people he sounds like he knew he was going to die what sad song.this song deserves top3

29 Beautiful - Eminem

This song can help people that get bullied at school just because they are different.

It's very emotional and it makes me cry every time I listen to this song, but it helps me get over being bullied.

Really deep song, the chorus almost makes me tear up.

30 Slippin' - DMX

DMX talks about his mom beating him, being left by his dad, drug addiction and a lot of other stuff.
I don't care what anyone says, best of all time

31 Cleanin' Out My Closet - Eminem

Really? Not even on the list while it should be first?

My favorite Emimem song, and it has been as long as I've listened to Emimem. - theOpinionatedOne

32 Lonely - Akon
33 I Tried - Bone Thugs-N-harmony
34 Hands Held High - Linkin Park
35 How Could You Leave Us - NF

Do any of these other songs contain the artist openly crying on the mic? I don't think so. NF's songs always contain raw emotion, and this song is no exception. That emotion, paired with the terribly sad topic of his mother "choosing" pills over him, culminates in a song that easily should at the top of this list.

Every time I listen to this song, I get angry and so sad as if my mom left but she is with me. It gets you. Especially when you know the words

It’s almost impossible to watch the music video without tearing up, and this is the only song that’s powerful like this

36 All that I Got is You - Ghostface Killah

How the hell on earth is this 41? Definitely top 10. And Eminem's drama is 7? Wow!

This should easily be top ten. Still makes me emotional listening to this. I remember Ghostface himself saying grown men coming up ro hi. Saying the song made them cry.

It should be number 1!

This is song will make the most aggressive thug cry, GFK was coming straight from the heart on this joint.
My moms played this for us when we couldn't sleep at home in the winter since she couldn't afford the gas, and we slept her car with the engine running.
If you can relate to this song, you DEFINITELY know the feels your neighbor or the people in similar situations you were/are in.
I love this song, but man it's something ya can only listen to when ya can't hold it in and when ya need to let it out.
One love, and hope you (the reader) has good day and a better tomorrow.
Peace 😊

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37 Kim - Eminem

"You loved him, didn't you" This song is one of the saddest and stunning songs I've ever heard, the pure heartbreak in the lyrics and voice is enough to make someone feel broken.

just listen to it.. it shows the real roar of person hurt deep..

38 Space Bound - Eminem

Very touching, relatable, raw song about the harm and evilness behind love and romance. Eminem truly opens up with sentiment in a sad love story ballad.

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39 Listen to Your Heart - Eminem
40 The Last Emperor - One Life

He's maybe the most underrated mc ever!

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41 Yesterday - Atmosphere

This should definitely be in the top 10. It's about him reminiscing and then regretting all the times he could've been hanging out with his dad, and he didn't. The song starts off with the narrator passing by someone on the street who looked like someone he knew and loved. As the song goes on, you learn more and more about this person, especially when he says that he'll endure all the criticisms if he could again, giving you somewhat "parent" vibe to the song, and then he says, "I know it wasn't you, cause you past away, dad."

42 U - Kendrick Lamar

This song and suicidal thoughts should be on this list

This should be up there

See. This song off to pimp a butterfly is tight. It's a sad song. He litterly loses it In the second half of the song

43 Going Through Changes - Eminem
44 Hailie's Song - Eminem

Beautiful song

45 So Sick - Ne-Yo
46 Hope - Twista
47 Runaway - Kanye West

Most emotional song ever, I almost cried the first time listening to this. So sweet, gotta love KanYe.

48 The Prayer - Kid Cudi

Super sad song, it gives me the chills every time I listen to it

49 A Million Lives - Jake Miller
50 The Book of Soul - Ab-Soul

If you understand the meaning of this you'd put it up there

For context: this song is about Ab-Soul's girlfriend, Alori Joh, who committed suicide by jumping off of a radio tower. It's so heartfelt, and heartbreaking, and honestly this should be number 1. At least the top 5.

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List Stats

2,000 votes
140 listings
7 years, 129 days old

Top Remixes (8)

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
1. Dance - Nas
2. I'll Be Missing You - Puff Daddy
3. Mockingbird - Eminem

View All 8

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