Saddest Rap Songs

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The Top Ten

1Stan - 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. :(
 More comments about Stan - EminemListen to sample

2Dance With the Devil - Immortal Technique
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.
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
its the saddest one, but the crossroads is my favourite in this list... how can I used to love h.e.r. be in that position? it shouldn't even be in this list
 More comments about Dance With the Devil - Immortal TechniqueListen to sample

3Heather 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.
 Listen to sample

4When I'm Gone - Eminem
touching song about his family.
It makes me think of how my family is right now, and how at some point in life things can just go wrong.
Hecks to the yeah!
 Listen to sample

5Brenda's Got a Baby - Tupac Listen to sample

6Good 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.. :(
 Listen to sample

7Mockingbird - Eminem Listen to sample

8Rock Bottom - Eminem

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, 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.

 Listen to sample

9I'll Be Missing You - Puff Daddy, Faith Evans & 112 Listen to sample

10I Used to Love H.E.R. - Common Listen to sample

The Contenders

11Difficult - 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.

SO SAD the only song that has every made me cry

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

12Norm Ender - Son Uyku

13Beautiful - Eminem

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

 Listen to sample

14The Crossroads - Bone Thugs-n-Harmony Listen to sample

15You Never Know - Immortal Technique

A story that has a realistic, sad and touching ending

 Listen to sample

16Cleanin' Out My Closet - Eminem
This song is one of my fauorite saddest rap song
 Listen to sample

17Hold Ya Head - The Notorious B.I.G. & Bob Marley
Remix of suicidal thoughts
 Listen to sample

18No More - Will Smith

SO UNDERRATED JUST LISTEN TO IT. IT IS SO TOUCHING YOU WILL LOVE THE SONG. IT IS KINDA HEARTBREAKING. WILL SMITH IS A GREAT RAPPER DEFINITELY. HE MAKES GOOD SONGS NOT, GANGSTER STUFF. BUT SONGS FOR EVERYBODY THAT'S WHY HE IS WORTH LISTENING TOO. I DIG HIS MUSIC. PEACE OUT TO WILL SMITH BEST FLOW MUCH LOVE (;

 Listen to sample

19One Life - The Last Emperor ft. Too Poetic & Esthero

20Kurt Kobain - Proof

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

 Listen to sample

21Airplanes, Pt. II - B.o.B Listen to sample

22So Hard to Breathe - B.o.B Listen to sample

23Hands 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!
One of the saddest, longest and meaningful rap song. Accept Lnkin Park, there's no band that can rap like Mike Shinoda
It is the World's best sad rap Song performed by world's best band "LINKIN PARK"
 Listen to sample

24Choices (A Wave For Alex) - Charles Hamilton

25Live In the Sky - T.I. Listen to sample

26Crew Love - Drake Listen to sample

27The 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

 Listen to sample

28Last Sad Song - Tech N9ne Listen to sample

29Same Love - Macklemore
How is this also not on the list.
 Listen to sample

30Tearz - Wu Tang Clan Listen to sample

31Ashes to Ashley - Sadistik Listen to sample

32November - Sadistik Listen to sample

33Happy Birthday - Flipsyde Listen to sample

34Wings - Macklemore
How is this not on the list?

35Kim - Eminem
It may seem like an anger song but I believe it's a sad song
 Listen to sample

36Otherside - Macklemore
I can't stop bumming this song!
 Listen to sample

37Hailie's Song - Eminem Listen to sample

38Last Chance - ABK Listen to sample

39Why - Nate Dogg

40Security - Royce Da 5'9'' Listen to sample

41How Come - D12 Listen to sample

42Kenji - 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
 Listen to sample

43Wicked Games - The Weeknd Listen to sample

44If I Had - Eminem Listen to sample

45Love Comes & Goes - Ed O.G. Listen to sample

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      List Info

      This list was created 2 years, 97 days ago and has been voted on over 500 times.

      Updated Tuesday, May 21, 2013

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