Saddest Rap Songs

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The Top Ten

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.

Brings tears to my eyes every time I listen to it. :(

The first time I listened to this I was immersed in the story and was engaged. Just an awesome song with a depressing story

V 45 Comments
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

Stan actually wasn't sad but this one is REALLY sad.

V 39 Comments
3 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.

Man this song hits right in the feels.. Mad respect!

V 26 Comments
4 Dance with the Devil - Immortal Technique

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.

Messed up song at end but good all the way

V 52 Comments
5 Mockingbird - Eminem

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

I cry every. single. damn. time. when I listen to this song.
Keep the onions away from me, Em.

V 32 Comments
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

I love this song it's so emotional

V 20 Comments
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.. :(

I wish D12 made more songs like this

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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.

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

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.

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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

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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.

Deep sh##!

V 12 Comments

The Contenders

11 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

It's so depressing

V 9 Comments
12 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

You can hear the pain in his voice, he is just so real

V 6 Comments
13 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.

... best Eminem song.

V 11 Comments
14 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.

Should be higher. Great song from great rapper. R.I.P. Proof

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

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

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

I just loved adore Tupac. R.I.P MY HOMIE!

17 Brenda's Got a Baby - Tupac

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.

Beautiful song

V 6 Comments
18 All I Do - Hishaam

I can't find this, does it exist?

Can't find it

19 1 Day - Plies
20 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

21 Do Bad On My Own - Z-Ro

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

22 Blast Myself - Z-Ro
23 The Pain - Murs
24 How She Got Her Name - Boosie Badazz
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

V 6 Comments
26 Ill Mind of Hopsin 6 - Hopsin

More sad than Heather Nicole, I think this deserves to be in the top 10

The saddest thing about this song is that many people posted it on YouTube with pictures of their dead loved ones and family members ):

Lyrics are very deep and intense about a best friend addicted to drugs and how he deals with his life truly hop should be in top 10.

He lost his best friend and decided to make a song about it. Makes me cry whenever he gets into the pre hook

V 3 Comments
27 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!

28 Gone Bad (American Horror Story) - Boosie Badazz
29 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

30 Many Men (Wish Death) - 50 Cent

Sad since its true about how he got shot

Love this one

Sad but real

31 The Message - Nas
32 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

Gay Eminem stans caused this song to be at 33, when this should be 1. Actually the saddest song I've ever heard, unlike Eminem rapping about his rapes

V 3 Comments
33 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

Heard it first in a WWE clip..had to look for it..

V 1 Comment
34 Too Deep for the Intro - J. Cole
35 Suicidal Thoughts - The Notorious B.I.G.

This song is a masterpiece...

This song is the best

Exactly yo

Lol get this Feminem and Tuwack bs off the list and get Biggie the don up there

36 Hailie's Song - Eminem

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

Only hailie song I like

37 Tha Crossroads - Bone Thugs-n-Harmony

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

The Eminem dickriders are the reason why this is so low on the list.

V 1 Comment
38 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.

39 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

40 Beautiful Pain - Eminem

Super meaningful Eminem song. - letdot52

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

41 See My Tears - Machine Gun Kelly

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

So depressing. My life in a nutshell.

42 Norm Ender - Son Uyku
43 Soundtrack 2 My Life - Kid Cudi
44 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

45 Time After Time - Kid Ink

Listen to this it makes me think about my ex

46 All That I Got Is You - Ghostface Killah

Seriously, number 12? Ghost's childhood was way harder then Em's.

I love this song

This can bring a tear to my eye, better than all Eminems songs on here. dickriders

47 Jocelyn Flores - Xxxtentacion

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

48 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.

How is this not higher up on the list..

V 4 Comments
49 I Miss My Homies - Master P
50 Mind Playing Tricks on Me - Geto Boys
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List Stats

4,000 votes
184 listings
7 years, 306 days old

Top Remixes (16)

1. Beautiful - Eminem
2. Mockingbird - Eminem
3. See My Tears - Machine Gun Kelly
Duggo38
1. My Block - Tupac
2. All I Do - Hishaam
3. Until the End of Time - 2pac
cleff
1. When I'm Gone - Eminem
2. Mockingbird - Eminem
3. Beautiful - Eminem
eminemgreenday

WRemix
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