Saddest Rap Songs


The Contenders: Page 3XW

41Soundtrack 2 My Life - Kid Cudi
42Slippin' - DMX
43Hands 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"

One of the saddest, longest and meaningful rap song. Accept Lnkin Park, there's no band that can rap like Mike Shinoda

V1 Comment
44Ill 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

V3 Comments
45If I Had - Eminem

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

46One Day - UGK
47Sing 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

V3 Comments
48Hold Ya Head - The Notorious B.I.G.V1 Comment
49The Noose - Tech N9ne

How does tech not have at least 10 songs on this list do you people even listen to rap at all he raps some of the saddest stuff out there along with a slew of welcome to strange land songs a lot of his sadder kod songs should be on here

Good song sad though might be a song you don't wanna listen to bless

V1 Comment
50Otherside - Macklemore & Ryan Lewis

So sad that Macklemore is known for his overplayed radio hits rather than songs like Otherside. Definitely one of my favorite songs by him.

This song plays a sad story that many people go thorough, beautiful song.

V1 Comment
51So Hard to Breathe - B.o.B
52Wicked Games - The Weeknd
53One Life - The Last Emperor ft. Too Poetic & Esthero

This is the saddest song ever in my opinion. The first verse is great, but not sad really, but it's the second verse that really gets you. Too Poetic is rapping about his struggle with cancer, and it's hard to listen to. It's the most haunting verse ever written in my opinion.

54Dear 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

V1 Comment
55Kenji - Fort Minor

Mike is so good at rapping about wars... This song should have been a single. I almost cried when I first heard this song, and was in thoughts for like 10 minutes... Even now this song touches my heart. And obviously, this song never goes boring. Perfect song for a list like this

This song gives me goosebumps every time I listen to it. It can truly make you cry; can make you think. While listening you can just easily picture it out.

56Happy Birthday - Flipsyde

This song that reminds me on sad times...

57Lams - BahramV1 Comment
58Live In the Sky - T.I.

T.I. wrote this song right after his friend Big Phil passed away.T.I. put his heart into this one and I can't believe this ain't Top 10 material.

Tip shows his emotional side in this song. He completely puts his gangster attitude to the side in this song and let's everyone know they lose someone somewy or another, be it jail, the streets, or death.

59Kim - Eminem

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

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

60Dream Forever - Hopsin

This song paints a vivid imagery of that girl of your dreams that always disappears when you wake up, and the trauma of being lonely. Only song I've ever truly teared up to.

This song is the perfect song for a hopeless romantic just wishing life was as good as their dreams

V1 Comment
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List StatsUpdated 7 Dec 2016

3,000 votes
160 listings
5 years, 298 days old

Top Remixes (12)

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

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