Saddest Rap Songs

The Top Ten Saddest Rap Songs

1 Stan - Eminem

One of Eminem's best! And it's sad too. So much meaning here. This song deserves number1 - srogers900

The saddest song I, personally have ever heard. The character Stan in the song is an exellent reflection to tell us that we do some crazy things for celebrities.

best, crazy wordplay and narration, no more questions asked, enough said!

This song is extremely sad. I am Eminem fan and I think this one of his greatest song and saddest song of all time

2 When I'm Gone - Eminem

This song always makes me upset every time I hear it but its a great song but its so sad my friend cried when he heard it and his mom wont let him here it any more I mean he's singing about what to do when he's dead how is that not sad

touching song about his family.

Vote it's better than hops in it needs to go up at least one if not more so much meaning

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.

3 Dance with the Devil - Immortal Technique

So much better than eminem's stan and when Iam gone. People are so reatard dumbass

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

This song would be first if the sample used the end of the song. Mainstream listeners who haven't heard of IT probably don't see why it is on this list based on the sample this site gives.

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.

4 Difficult - Eminem

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.

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.

This song actually made my eyes water when I first heard it. One of my favorite songs by one of my favorite artists.

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

5 Mockingbird - Eminem

I relate to this song as do my parents. Separation, theft and loss, drugs, and an absent parent. It gives me solemn and comfort.

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

This Oscar just epic! The only rap smog that made me cry after difficult by em...

The best rap I have ever heard

6 Beautiful - Eminem

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"

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.

This song is so good but so depressing

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.

7 Good Die Young - D12

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

The good really do die young Pac, biggie, bugz and proof R.I. P - Norrisofchuck

The best sad song ever! R.I.P.. :(

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

8 I'll Be Missing You - Puff Daddy

A tribute to The Notorious BIG. The song is very emotional and the chorus made me cry.

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.

How is this 61, this is extremely sad. Puffy mourning his best friend, and Faith Evans mourning her husband

It makes me cry every time and I don't even like biggie like that

9 My Block - Tupac

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

Tupac is the inspiration of Eminem... Tupac was a legend and Eminem is the living legend

Best song ever... Touches your core

I love Tupac and this song is amazing

2Pac is the best rapper of all time

10 You Never Know - Immortal Technique

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

I cried when I first heard this track. Saddest song out of all of these.

Immortal technique in general touches the heart all his songs have strong meanings.

A story that has a realistic, sad and touching ending

The Newcomers

? Everyday Struggle - Notorious B.I.G.

The Contenders

11 Headlights - Eminem

I think if you are a true Eminem fan and you know his story there's no way this song wouldn't make you cry... He's been around for so long & in so many of his songs he's shared stories of his childhood and his life that for him to rap about forgiveness towards his mom it's so real and emotional... ONE of my favorite tracks ever... I tear up every time...

I wouldn't say that this song is a really sad song but more of a touching one because he forgives his mom for everything she ever put him through. I get goosebumps every time I hear it and if your a real Eminem fan you'll understand why.

I cried more listening to this song when I was 13 then I cried watching Titanic when I was 9. This is song is about how Eminem belies his mom is dying from because of the effects of Emienms lyrics to songs such as 'Cleanin out my closet'. To me this song is closely followed by Stan and Beautiful. If you listen to the lyrics closely in Beautiful you will realize it's very deep and very well written especially the Chorus.

Eminem forgave his mom after all she did to him to the lyrics are so good and sad

12 Rock Bottom - Eminem

Just listen to it, it shows how hard it was for Eminem to make it as a rapper. He had such a hard life that is so unimaginable how much he had to go through. This song is the best on The Slim Shady LP and deserves to be higher.

Very emotional lyrics, the beat is really depressing.

One of the saddest songs. Truly makes me sad to imagine what emi went through in the early dayz of his career. Just listen to this and you'll realize how touching Eminem songs can be

Just listen to it and you'll get very depressed for a few minutes. (Or that's what I had)

13 Kurt Kobain - Proof

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

The deepest personal confession of the greatest man to never see his true potential.

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.

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

14 Breathin' - T-Rock
15 Until the End of Time - 2pac

Glad it's in top ten:) Tupac is the best rapper of all time.

this song get me whenever I listened to it

Great song
Rest in peace 2pac

Tupac is the greatest until the end of time
And this song is the greatest until the end of time

16 All I Do - Hishaam

I can't find this, does it exist?

Can't find it

17 Sing for the Moment - Eminem

Underrated... easily his best single. It's one of his realest songs he's ever released and so many people can relate to it

This ain’t sad though

18 1 Day - Plies
19 Careful What You Wish For - Eminem

Eminem explains his struggles while he was in rehab, doing drugs, and finally recovering. He shows the hard points of being that famous it is just amazing.

A really sad Eminem song about fame and drugs.

20 Do Bad On My Own - Z-Ro

A song about loneliness, sadness, betrayal, and suicide.

21 Legacy - Eminem

A song about Eminem's struggle.. makes every true fan going through bad times.. cry

Amazing song, reaches deep into my soul every time I listen to it.

A song about his struggle as a kid to where he is now, sad song

Easily one of my favorite em songs, and it tells a story

22 Blast Myself - Z-Ro
23 Heather Nicole - Hopsin

This is a great song, buut I don't think it should be on top ten. Hopsin is a kind of new rapper who has great potential, but this song just doesn't cut it, there's plenty other sad rap songs that belong in this spot.

I've known this song for so long, dedicated to my relationship with this girl, which ended 11 months ago, listen to it and always think about her.

This is one of the best sad songs ever I wonder why it is not in the top 10

Old friend by hopsin is more real than any of these others. I don't even care much for rap but couldn't stop the leak before the end of the song

24 The Pain - Murs
25 Changes - Tupac

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.

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

I cried when I first heard this song.

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

26 How She Got Her Name - Boosie Badazz
27 Going Through Changes - Eminem

Why isn't this in the top 10? I think it's better than mocking bird if you looked into the lyrics you'd actually cry or something no matter what I'd never stop listening to this

The lyrics are really emotional. In the song, he raps about how he lost his friend Proof, and despite the fact that he divorced with Kim, he would still do anything for her. - ethanmeinster

Should be way higher

Beat is sad as hell

28 See My Tears - Machine Gun Kelly

Such an emotionally inspiring song. Touches my heart every time.

So depressing. My life in a nutshell.

29 I Tried - Bone-Thugs-N-harmony

I love bone thugs n harmony even though it's an oldie song in my eyes it means more to me and I'm 11 years old

I can't believe "that crossroads" isn't in top ten! This list is wrong as hell!

30 Gone Bad (American Horror Story) - Boosie Badazz
31 Dance - Nas

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

Great song

32 Brenda's Got a Baby - Tupac

I used to listen to this as a kid, it always brought sadness to me. But wow, it’s really eye opening.

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

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.

"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.

33 Many Men (Wish Death) - 50 Cent

Sad since its true about how he got shot

Love this one

Sad but real

34 The Message - Nas
35 Life Goes On - 2Pac

This song should be number 1. It's all about one of the friends that you grew up with and are really close to, it makes you imagine them dying. It makes you think of all the good times you had together, getting drunk, high, laughing, chilling and then think about them or yourself dying.

This song is amazing. It's hard for me to hold back tears when I listen to it. This is the first Tupac song I ever heard and I've been hooked on his music ever since.

Singing about the death of his homies and his own death. Tupac sang one of the greatest rap songs in the history of rap and the saddest/ most emotional

This is the saddest song ever made! Makes me so up set

He talks about his own death and how he wants to be buried

36 Too Deep for the Intro - J. Cole
37 Suicidal Thoughts - The Notorious B.I.G.

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

This song is a masterpiece...

This song is the best

Exactly yo

38 If I Had - Eminem

It is nice... sad... at all if you listen to it with high volume it will make you berserk... love it...

39 Jocelyn Flores - Xxxtentacion

Was very sad I also hate that it keep crying but it’s a sad so so it’s basically the whole point to cry.

One of the best heart warming songs ever, still in love with it.

Saddest I've ever heard

this should be #1

40 My Life - The Game

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

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

Music video is sad. Lyrics are emotional as well

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

41 Hailie's Song - Eminem

Great song! Eminem expresses the love and gratitude for his daughter! Just plain beautiful!

Only hailie song I like

42 Beautiful Pain - Eminem

Super meaningful Eminem song. - letdot52

One of the saddest Eminem song I've heard...

43 Like Toy Soldiers - Eminem

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

It speaks everyone's mind. Notorious BIG,Tupac,Proof,XXXtentacion all greats who died of crazy people

This song is great, but is so much better once you know the whole story behind it (Google helps)

This should be on the top 3

44 Kim - Eminem

It may seem like an anger song but I believe it's a sad song

It's more like a shocking song but I believe it's a sad song

Very shocking song loved it pure horrorcore rap mixed with emotion and anger


45 Tha Crossroads - Bone Thugs-n-Harmony

I remember listening to this as a kid and singing and rapping along to it with my dad in the car.

Yeah! Didn't expect this song so high but my faith restored! This was my jam!

The video messed me up as a child.

Give this a listen

46 Norm Ender - Son Uyku
47 The Book of Soul - Ab-Soul

Ab-soul goes through his tragic life story in the most real way possible

Really deep song about ab's girlfreind of 7 years commiting scuicide

Love it you can hear the pain in the instrumentals🖤☹️

48 Dead and Gone - T.I.

Everything & everyone will eventually be dead & gone. Depressing & sad yes but that's how it it.

This is also almost the saddest song Justin Timberlake has ever made. - Sjinkiie

Justin Timberlake crushed it

Best one on this list.

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

One of the saddest most descriptive songs of all time, best rap song in a while in my opinion

Really had me to tears the first time I heard it, Kendrick's past is just too sad.

By far one of the most saddest, descriptive, and deep rap songs EVER.

Just listen to all 12 minutes of it and you will cry

50 Hurt Me Soul - Lupe Fiasco
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