Saddest Rap Songs


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. :(

So Many Em Songs in here hard to choose one. - TheHeroinFather

V 43 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 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

Much eminem

V 31 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.

Best rap song ever maybe

V 51 Comments
5 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've never heard this song๐Ÿ˜‚๐Ÿ˜œ...but I think I will like it๐Ÿ‘

V 19 Comments
6 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.

How is this not #1? If everyone had heard this I guarantee it would be #1.

V 25 Comments
7 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

V 6 Comments
8 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
9 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.

Not one song has ever made me cry until I listened to this. I've listened to all the Eminem songs above this and they were no where NEAR the sadness of this one.

V 9 Comments
10 All I Do - Hishaam

I can't find this, does it exist?

Can't find it

The Contenders

11 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!

12 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

V 8 Comments
13 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

Its very sad

V 4 Comments
14 The Pain - Murs
15 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
16 Many Men (Wish Death) - 50 Cent

Sad since its true about how he got shot

V 2 Comments
17 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
18 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
19 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!

20 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

V 2 Comments
21 See My Tears - Machine Gun Kelly

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

So depressing. My life in a nutshell.

22 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
23 Too Deep for the Intro - J. Cole
24 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.

25 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
26 Hailie's Song - Eminem

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

Only hailie song I like

27 Dance - Nas

Great song

28 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.

29 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

30 I Miss My Homies - Master P
31 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

32 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

33 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

V 1 Comment
34 Tearz - Wu Tang Clan

RZA's verse is what makes this song way more depressing than you would expect. Not just because of the death of his brother, witch is already depressing enough on it's own, but because of the way he presents the story. Like when he doesn't want to say that his brother is dead, so he stops and yells AW MAN!. But the really haunting part is his voice, because it doesn't sound sad or anything like that, it sounds like ha has difficulty breathing and like he is losing his mind, or has already gone insane, and the part where you can really notice that is when he starts laughing like a maniac for a moment. Oh and the song might just have the best production for a depressing track ever!

35 Soundtrack 2 My Life - Kid Cudi
36 The Book of Soul - Ab-Soul

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

V 1 Comment
37 Time After Time - Kid Ink

Listen to this it makes me think about my ex

38 Slippin' - DMX

This should be number 1 what

Easily best song on this list

39 Mind Playing Tricks on Me - Geto Boys
40 Norm Ender - Son Uyku
41 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...

42 One Day - UGK
43 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.

RIP Proof, Very underrated

V 2 Comments
44 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
45 Hands Held High - Linkin Park

Oh how I love mike... He's a very good rapper but when it comes to rapping about wars, he's exceptional... "kenji" is kind of better... But this too is great!

It is the World's best sad rap Song performed by world's best band "Linkin Park"

This song gave me the chills when I first heard it.

I love LP. Mike is amazing and this song is amazing

V 1 Comment
46 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
47 Sing for the Moment - Eminem
48 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


49 Dear Mama - 2pac

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.

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

Yeah look on every other list eminem will be second or third

This made my appreciate what my mom does for me - SoloPotato

V 2 Comments
50 Happy Birthday - Flipsyde

This song that reminds me on sad times...

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List Stats

4,000 votes
172 listings
7 years, 34 days old

Top Remixes (15)

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

View All 15

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