Saddest Hip Hop Songs

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The Top Ten

1 Stan - Eminem Stan - Eminem

In my opinion this song causes you to be more shocked than it makes you emotional. For me you feel no sympathy for this fictional character created by Eminem, I can see why some people might feel sorry for him, his parents and overall childhood has made him the aggravated and destructive person that he has turned into when reaching adulthood. However I don't feel sorry for him, his death was deserved because of all the things he did that could have been avoidable, like cutting himself because it gives him adrenaline, not understanding that Eminem is a very busy and popular rapper, it was a surprise he even had time to answer Stan's letters, and of course his rage leading to the death of his girlfriend and unborn baby. I think songs like "Dear Mama" or "Mockingbird" have more of an effect, mainly because everything that they are is saying is relatable. With Pac's song expressing his love for his mum, and how she got him through his childhood despite all the difficulties that he faced. ...more - Allen21

To deep to even comprehend

This song is great for being so sad

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.

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

The song was to Biggie, but listening to the lyrics, it seems like it could go out to anyone really. It’s such a good but sad 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

10 Comments
3 Dance - Nas Dance - Nas

Such a sad song

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 "

4 Comments
4 Dance with the Devil - Immortal Technique

Needs to be number 1, the story telling can't be compared

This has gotta be number 1. I mean Eminem's Stan is pretty sad too but no other Hip Hop song can beat Immortal Technique's Dance With The Devil. Even 4 is too low for this. Get it to number 1. - DarkBoi-X

Eminem is so overrraateeeddd

Saddest song I've ever heard

20 Comments
5 When I'm Gone - Eminem

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

I can relate

"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.

10 Comments
6 Dear Mama - 2Pac

R.I.P 2Pac I love this song so much - BreakFastBeast2005

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.

10 Comments
7 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 :'(

Talking bout his baby who he never got to see cause his girl had a miscarriage. Love slim shady but this has got to be one

1 Comment
8 Mockingbird - Eminem

Family. Means. Most

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.

9 Comments
9 Brenda's Got a Baby - 2Pac

The theme this song explores is something a lot of countries including America experience. in my opinion, one of the best rap songs of all time.

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.

4 Comments
10 My Life - The Game

One of the tightest songs on here

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

The Contenders

11 Changes - 2pac

This song gives me chills. - The01Bro

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

2 Comments
12 Like Toy Soldiers - Eminem

The story of Eminem 50 cent and dre beefs with Eminem having enough of his people dying or getting hurt

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

Story about increasing violence in hip hop

My favorite of his songs. - letdot52

2 Comments
13 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.

14 Thank You - Xzibit
15 Breathin' - T-Rock
16 Blast Myself - Z-Ro
17 Suicidal Thoughts - Notorious B.I.G.

A great song about Biggie's inside demons

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

4 Comments
18 Hail Mary - 2Pac

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

How is this sad?

19 1 Day - Plies
20 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.

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...

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.

9 Comments
21 Love the Way You Lie - Eminem

This sucks. Stop worshiping and spamming Eminem on every list! - RobertWisdom

Love this song with passion

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

This isn't sad, just angry

2 Comments
22 Gone Bad (American Horror Story) - Boosie Badazz
23 Pain No More - SNO
24 Hurt Me Soul - Lupe Fiasco

Best rap song of all time

25 Lost Ones - J Cole

Legend of the game. No words.

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

3 Comments
26 Hey Mama - Kanye West

Kanye the legend

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.

Sad song

27 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

This is one of all time favorte songs... Analyse and think...

1 Comment
28 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...

29 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.

THE BEST HIP-HOP SONG EVER! #kingkendrick

30 How Could You Leave Us - NF

How could you leave is a very meaningful song, I could never imagine losing my mom out of all the songs on this list this deserves number 1.

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.

A sad relatable song for many nf is an all time legend ily nf thanks for all you have done for me

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

2 Comments
31 Lesson Learned - Lil Wyte
32 The Crossroads - Bone Thugs-N-harmony

Incredibly touching

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

2 Comments
33 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.

34 Beautiful - Eminem

The depression in this song is extremely relatable. This is like the anthem for depression. He talks about feeling alone, isolating yourself, anxiety. Real deep

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.

35 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

36 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

37 Life Goes On - 2pac
38 Roses - Kanye West
39 Lonely - Akon
40 All that I Got is You - Ghostface Killah

Should be top 5 easy

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!

2 Comments
41 I Tried - Bone Thugs-N-harmony
42 The Prayer - Kid Cudi

Love it... It's my anthem

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

This song has helped me get through some difficult times. At one point, I didn’t think I’d make it out of a dark place I was in. I went as far as telling those close to me how I truly felt about them and I accepted whatever the outcome would be for me. I’m still working on myself, but I made it.

43 Hands Held High - Linkin Park
44 U - Kendrick Lamar

Truly one of the saddest songs of the century

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

45 Listen to Your Heart - Eminem
46 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."

47 Going Through Changes - Eminem
48 Hailie's Song - Eminem

Beautiful song

49 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..

50 The Last Emperor - One Life

He's maybe the most underrated mc ever!

Everyone who knows this song will vote for it... really.

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List Stats

2,000 votes
160 listings
9 years, 35 days old

Top Remixes (9)

1. I'll Be Missing You - Puff Daddy
2. Dear Mama - 2Pac
3. Hail Mary - 2Pac
bo7anon
1. Dear Mama - 2Pac
2. Stan - Eminem
3. When I'm Gone - Eminem
DK
1. Breathin' - T-Rock
2. Blast Myself - Z-Ro
3. 1 Day - Plies
DaWyteNight

WRemix
View All 9

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