Saddest Hip Hop and Rap Songs

The Top Ten
1 Stan - Eminem Stan - Eminem Cover Art

Its not emotional unless you have been in a abusive relation ship which a lot of people haven't gone through. But to the people that have gone through this, it can be very emotional. In my opinion. In my opinion this isn't number 1. Em has more emotional songs.

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

Eminem is been my favorite rapper since I was young. Everything he raps about it touches my heart. What I really realized about Eminem is that he does not rap about money,style or fame but all he does is to rap about life, the struggle that people have, pain people experience and the gain of success in other people lives. I like shady's song but more especially my favorite song is Hallie. The way he raps about Hallie I feel like she's my own daughter.
This post is from Anele Mangcotywa from South Africa the country of rainbow nation.
Eminem Marshall Bruce Mathers keep doing it you the best of all times.

One of his best. It's sad because the character Stan is trying to get in touch with his daughter after their relationship failed during childhood, and she won't respond. He keeps on trying to keep in touch but every time she fails to respond he keeps doubting what the truth really is by coming up with excuses to back up the lies, when he really knows that she doesn't want him in her life anymore.

2 I'll Be Missing You - Puff Daddy I'll Be Missing You - Puff Daddy Cover Art

This made me stop and think what all these rappers have been through, Eazy-E with the HIV-AIDS, Tupac and Biggie shot to death, it just hit me and all of these rappers I have much respect for.

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

Everything about this song is emotional, the lyrics, the beat, the sound of pain in his voice and especially the chorus. This song deserves to be number 1

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.

3 When I'm Gone - Eminem When I'm Gone - Eminem Cover Art

I would have never ever thought that this song would make me cry. I've listen to many emotional songs but this one is the only one that makes me cry even if I can't relate. Just not being around a loved one is emotional sometimes but to begone trying to support your family and having to travel without seeing your kids is very emotional.

Every time I listen to this song I get tears in my eyes when Haley talks to him at the concert in Sweden. It's one of the most emotional songs from Eminem along with Mockingbird that really demonstrate his talent for writing touching lyrics and how much he loves his daughter.

The most inspirational rap song ever! The emotion was very nicely used and very touching too the most saddest song ever
P.S. I didn't find Stan too be sad but I felt bad for his fan at the end.

I love the way eminem shows his true dedication to his family and in someways you could say that he questions the critics over how dedicated they are to their family e.g. " have you ever loved someone so much you'd give an arm for, not the expression literally given on for".

4 Dance with the Devil - Immortal Technique Dance with the Devil - Immortal Technique Cover Art

The only reason this isn't number one is because a lot of people haven't heard it. I can almost guarantee everyone who has heard it, voted for it. I'll never forget the first time I heard this song, it affected me in a way that no song has ever before. You Never Know is another amazingly sad song by Immortal Technique which I would put at number 2.

There is really too much I can say about this song that will take up tons of space but ill just say this: its an EPIC song that if you haven't heard, you NEED to hear. Even if you don't agree with the subject matter, the execution of this story can hook you in just before the first chorus

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.

Immortal has a storytelling ability that's better than anyone I've ever heard. His other song You Never Know is a great story that is just as sad. It should definitely be on this list instead of I Used to love HER.

5 Dance - Nas Dance - Nas Cover Art

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!

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

Its such a sad song and deserves to be higher, its about how much he wishes to see his mom again who died and talks about what he remembers about her, he sings the verse himself making it sound realer

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.

6 Mockingbird - Eminem Mockingbird - Eminem Cover Art

The most emotional part is when he says he can't afford Christmas presents for his daughters. It's emotional and seeing this now when this whole pandemic makes it very sensitive to listen too though.

This song reminds me of my childhood in a way. My mom and dad broke up and she left and never came back. My dad did everything for us and yet, I stilled cryed at night for my mom. He would tell me Jimmy's gonna be alright. This song should be in the top ten

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 song is lyrically brilliant and this is so sad that it gets me depressed and thinking whenever I listen to it. somebody made a mix of this song and better days by Tupac and it made me cry.

7 Difficult - Eminem

I listen to this every day. It has such a sad tone that you can tell Eminem is having lots of trouble actually saying the words, his voice is trembling in the whole song. It makes me realize how easy we receive life compared to others like Eminem that had to deal with his father leaving and never coming back when he wasn't even a year old, then Eminem dealing with a abusive mother that made him pay for the house bills even though she would kick him out the house, to being beat up by bullies and transporting schools who knows how many times, finally he had to deal with having his daughter Hailie by working extremely hard.

I know the only reason this isn't number one is because most people haven't heard this. This song was never supposed to be released but was leaked. By far the saddest rap I've ever heard. Please listen to this if you haven't done so.

This is definitely the saddest song by Eminem if not any rapper. I'm a diehard Eminem fan and when I heard this song it blew my mind at the amount of emotion and love he puts in this song for his friend. RIP Proof

This should honestly be number one. If you've never heard it look it up. It hits hard if you ever lost anyone, or just if you have a heart. Can really hear the pain in his voice in this one.

8 Dear Mama - 2Pac Dear Mama - 2Pac Cover Art

What? it's the greatest rap song of all time by the greatest rapper of all time.. I like Eminem but there's a lot of his young fans in this website, even they voted for him for the best rapper now he's the 1st and he's above 2Pac. Eminem knows that Pac is the greatest and he said it before that's why I got much love for him.

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

2Pac's tribute to his mama really makes me feel emotional. Great song with powerful lyrics

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

9 Brenda's Got a Baby - 2Pac Brenda's Got a Baby - 2Pac Cover Art

"She sees sex as a way of leaving Hell, it's paying her rent so she really can't complain"
I love the passion Tupac has for women and their liberation. He brought to everyone's eyes the harsh reality of being a young girl in the ghetto with no guidance. Too bad there aren't more rappers this passionate.R.I.P. to the greatest lyricist of all time.

It's the tone of hopelessness in this song that touches me greatly. This song is talking about a real issue, not like Eminem who is rapping about his own troubles. It opened many eyes, including mine whereas listening to, for example, Mockingbird by Eminem just made me pity him and had no real impact on me.

Talks about the issues of an individual, in this case Brenda, and relates it to a wider social problem across ghettos that communities face. Really eye-opening, especially if you're of the type that blame an individual's failures on that one person, rather than regarding the circumstances they were born into

Four Eminem songs at the top?

This is the saddest hip hop song of all time, no arguments. Some songs here are simply scary, but this song is so sad because we all know it happens every day. No Eminem songs make it in the top 10. Dear Mama is number 2, I Used to Love Her number 3

10 Beautiful - Eminem Beautiful - Eminem Cover Art

This song just makes me emotional. The hook speaks to me and probably many others with self confidence issues. It's an intriguing mix because the verses are so sad and the hook is so uplifting. The sampled bit to start and end the song are great as well as well as Em's quote at the end "god gave you them shoes to fit you, so put them on and wear them. Be yourself man, be proud of who you are. Even if it sounds corny don't let no one tell you, you ain't beautiful"

Not surprised an Eminem song is here, considering how amazing he is lyrically. But this should be number 1, it is the most emotional Eminem song. Then Dance with the Devil should be 2 because Immortal Technique is also very good.

This song is so sad. But I love it. Eminem is the only one that can do this. He just the was he lyrically puts words I don't know. It's not suprising to find this song here honestly, it's one of my very favorite even though it's so depressing.

I just think this song really reflect on the people who get picked on at school because they are them self they don't care what everyone thinks.

The Contenders
11 Suicidal Thoughts - Notorious B.I.G. Suicidal Thoughts - Notorious B.I.G. Cover Art

This is one of my go to song when I'm severely depressed, ( I'm Sorry by Joyner Lucas and Broken by Lund are the other two ). It makes me just get all of my emotions out. I listen to this because it's stopped me quite a few times from going too far.

This is real talk right here with the lyrics. Still gives me chills years later.

Song really relatable and it really helps me.

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

12 Happy Birthday - Flipsyde Happy Birthday - Flipsyde Cover Art

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.

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

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

This song that reminds me on sad times...

13 Changes - 2pac Changes - 2pac Cover Art

I cry when I hear the opening piano music. I just break down knowing that he's gone, and it really showed how good a guy Tupac was, and how much of a change he wanted to make. I listen to the song, and I wonder," Why Tupac, of all people, why was Tupac taken from us? " This song is really just his legacy.

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

Tupac talks of hope, in a tone of hopelessness. The juxtaposition of these two emotions makes for a beautiful song.

This deserves the top 10's. It is about what he has been through and he just wanted peace.

14 My Life - The Game My Life - The Game Cover Art

This song should be number one. My Life by the game packs so much behind it, absolutely amazing.

Can't believe this song wasnt on the list yet.. Its sad but it is so much like my past was... It brings tears to my eyes every time

Love this song but if you want to hear more sad songs by him listen to bloody moon bonus track, monsters in my head and some others

15 Like Toy Soldiers - Eminem Like Toy Soldiers - Eminem Cover Art

The chorus and starting of the song is very emotional for me, I was suprised because it should at least be in the top 20.

This should be much higher, higher than all the other Eminem songs on here. I've cried a few times to this

It's about how Bugz died because of rap beef, Em feels responsible. Fun fact: Proof portrays Bugz I'm the video, and is later killed

My favorite of his songs.

16 Runaway Love - Ludacris Runaway Love - Ludacris Cover Art

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.

This song hurts my feels. I cried the first time I listened to it

17 Thank You - Xzibit Thank You - Xzibit Cover Art
18 Good Die Young - D12 Good Die Young - D12 Cover Art

It's a really great song with in depth lyrics that allow you to see a different side of the members of D12.

I can't listen to Kuniva's verse without starting to tear up, when he raps you just feel what he's saying so deeply.

Really makes you shed a tear man... It should be on the first place..

R.I. P Proof and Bugz this should be at least in the top 10 I don't get why it only has 2 percent of people liking this

19 Kurt Kobain - Proof Kurt Kobain - Proof Cover Art

One of the best rappers that's existed but because he's so underrated nobody listens to him anymore. This a amazing song written by him.

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

Such a great song. I tried to make at top ten proof song list and it still hasn't been published.

Proof is such a underrated rapper. This whole album is dope and this song gets the eeriest things across about him

20 Love the Way You Lie - Eminem Love the Way You Lie - Eminem Cover Art

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

21 You Never Know - Immortal Technique You Never Know - Immortal Technique Cover Art

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.

Immortal technique is unique in the rap game he raps about real life issues and politics, not just words rhyme like a skilled Dr Suss that make no sense or only rap about sex drugs and money. Most rappers are materialistic and the most cocky biggest ego D bags in the world. This is the reason I don't like rap Immortal Technique changed that for me.

Many songs can touch your heart, but this song just grabs your heart and crushes it such a sad song. On my personal top ten ALL TIME

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.

22 Slippin' - DMX Slippin' - DMX Cover Art

Makes me sad every time I listen knowing he died recently, this song tells about his rough past and how he chased his dream. Long live X

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

23 Breathin' - T-Rock Breathin' - T-Rock Cover Art
24 My Block - 2Pac My Block - 2Pac Cover Art

I hate how this whole website of full of Eminem fans, it provides a very bias list.

Best song ever... Touches your core

Lovely song and deep

Yeah eminem isn't the best rapper ever just because he is white tupac and biggie were the best

25 I Seen a Man Die - Scarface I Seen a Man Die - Scarface Cover Art

Real deep top ten worthy

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