Saddest Rap Songs

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The Contenders: Page 2XW

21See My Tears - Machine Gun Kelly

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

So depressing. My life in a nutshell.

22Changes - 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.

No comment for this song too many words too describe it

V4 Comments
23The 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.

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

V1 Comment
24Careful 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.

25Too Deep for the Intro - J. Cole
26Hailie's Song - Eminem

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

V1 Comment
27Dance - NasV1 Comment
28Dead 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

V1 Comment
29All That I Got Is You - Ghostface Killah

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

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

V1 Comment
30My 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

31Suicidal Thoughts - The Notorious B.I.G.

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

V2 Comments
32Norm Ender - Son Uyku
33Tearz - 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!

34Going 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

V1 Comment
35The Book of Soul - Ab-Soul

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

V1 Comment
36Time After Time - Kid Ink

Listen to this it makes me think about my ex

37Soundtrack 2 My Life - Kid Cudi
38Slippin' - DMX
39Kurt 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.

V1 Comment
40If I Had - Eminem

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

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List StatsUpdated 3 Dec 2016

3,000 votes
160 listings
5 years, 294 days old

Top Remixes (12)

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. I'll Be Missing You - Puff Daddy
2. Difficult - Eminem
3. Good Die Young - D12
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