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. :(
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2Mockingbird - 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
Amazing... Just amazing... Makes my heart beats go faster...
I m sure this the best song ever by Eminem... His lyrics are just great... Tis song toally rocks... Seriously... !
This Oscar just epic! The only rap smog that made me cry after difficult by em...
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3When I'm Gone - Eminem
touching song about his family.
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
Vote its better than hops in it needs to go up at least one if not more so much meaning
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4Dance 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
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.
More comments about Dance With the Devil - Immortal TechniqueListen to sample

5Beautiful - 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
Not surprised an Eminem song is here, considering how amazing he is lyrically. But this should be number 1, it is the most emotional Eminem song. Then Dance with the Devil should be 2 because Immortal Technique is also very good.
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6Brenda's Got a Baby - Tupac
"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.
Shut up idiot Eminem is number one not because your black he is not number 1 I'm black and I know this I Crazy but some black people thinks Eminem is Number one even my friend is black he thinks he number one and a lot of white people thinks Eminem is Number one cause I just ask White Girls I know who is number 2 mac miller-star room
Already shocked by this song
More comments about Brenda's Got a Baby - TupacListen to sample

7See My Tears - MGK
Such an emotionally inspiring song. Touches my heart every time.
Gay ass song. It makes me wanna blow off my head and skin a cat.

Dengel10

Listen to sample

8My Block - Tupac
I hate how this whole website of full of Eminem fans, it provides a very bias list.
Lovely song and deep
Listen to sample

9Heather 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
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10You 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.
A story that has a realistic, sad and touching ending
More comments about You Never Know - Immortal TechniqueListen to sample

The Contenders

11All That I Got Is You - Ghostface Killah Listen to sample

12The Crossroads - Bone Thugs-n-Harmony Listen to sample

13All I Do - Hishaam

14Until the End of Time - 2pac
Glad it's in top ten:) Tupac is the best rapper of all time.
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15Time After Time - Kid Ink

16Hailie's Song - Eminem Listen to sample

17Many Men (Wish Death) - 50 Cent Listen to sample

18I Miss My Homies - Master P Listen to sample

19Difficult - 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.
This song actually made my eyes water when I first heard it. One of my favorite songs by one of my favorite artists.
I love this song. It was what made me get into Eminem in he first place. By far his saddest and probably his best. More people need to hear this.
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20Dead and Gone - T.I.
Everything & everyone will eventually be dead & gone. Depressing & sad yes but that's how it it.
Best one on this list.
Listen to sample

21The Pain - Murs

22One Day - UGK Listen to sample

23Good 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.. :(
More comments about Good Die Young - D12 Listen to sample

24Slippin' - DMX Listen to sample

25Tearz - Wu Tang Clan Listen to sample

26Legacy - Eminem
A song about Eminem's struggle.. makes every true fan going through bad times.. cry
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27Soundtrack 2 My Life - Kid Cudi Listen to sample

28Norm Ender - Son Uyku

29Careful What You Wish For - Eminem
A really sad Eminem song about fame and drugs.
Listen to sample

30Too Deep for the Intro - J. Cole

31Rock 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
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32Going 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
Why on earth is this 53 saddesed song ever just listen to the lyrics. Eminem is the best rapper in the game.
His new song "berzerk" is pretty damn good as well
Whoever thinks its bad don't know anything about rap.
Sad and depressing song though👍😢
Listen to sample

33My Life - The Game
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
Listen to sample

34Do Bad On My Own - Z-Ro
A song about loneliness, sadness, betrayal, and suicide.
Listen to sample

35I Used to Love H.E.R. - Common Listen to sample

36Hands 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
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37The Book of Soul - Ab-Soul
Really deep song about ab's girlfreind of 7 years commiting scuicide
Listen to sample

38Ill 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.
More comments about Ill Mind of Hopsin 6 - Hopsin

39If I Had - Eminem
It is nice... sad... at all if you listen to it with high volume it will make you berserk... love it...
Listen to sample

40Watch How It Go Down - Termanology Listen to sample

41Kurt Kobain - Proof
The deepest personal confession of the greatest man to never see his true potential.
Just Connects, must listen
Listen to sample

42The 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
One of the saddest songs ever... Just listen to it.
Listen to sample

43You Got Me - The Roots Listen to sample

44Hold Ya Head - The Notorious B.I.G. & Bob Marley
Remix of suicidal thoughts
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45So Hard to Breathe - B.o.B Listen to sample

46Otherside - Macklemore
So sad that Macklemore is known for his overplayed radio hits rather than songs like Otherside. Definitely one of my favorite songs by him.
I can't stop bumming this song!
Listen to sample

47One Life - The Last Emperor ft. Too Poetic & Esthero

48Dance - Nas Listen to sample

49Happy Birthday - Flipsyde
This song that reminds me on sad times...
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50Live 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.
Listen to sample

51Wicked Games - The Weeknd Listen to sample

52No 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

53Airplanes, Pt. II - B.o.B
Fantastic song. Eminems verse was my real eye opener about life. It taught me that if I ever want to accomplish my goals, I have to work for them, they wont just come to U. Seriously worth listening to, and deserves to be higher.
Listen to sample

54Crew Love - Drake Listen to sample

55Last Sad Song - Tech N9ne
Very good song about Tech N9ne thinking about his singing and how people like his sad songs and how itll be his last one.
Listen to sample

56Kenji - 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.
Listen to sample

57The Prayer - Kid Cudi
Awesome song, very sad, and has a lot if meaning to it!
"And if I die before I wake, I pray to lord my soul to take." Need it say more?
Good enough to match up to Eminems best (This is comming from a die hard em fan)

58Rebecca - Grieves
Really great song. You should give it a listen
Such a good song
Listen to sample

59Letter to My Father - Caskey

60Choices (A Wave For Alex) - Charles Hamilton

61Why - Nate Dogg
I can't find this song

I'am sure that if any body listen that song will arrange it as nmb one.

62November - Sadistik
This is such a good song should be top 20 at least
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63Same Love - Macklemore
How is this also not on the list.
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64Goodbye - Slaughterhouse
Deep R.I.P. song. Each rapper from the group slaughterhouse had lost someone recently so they made this very emotional song in homage.
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65The Message - Grandmaster Flash & The Furious Five
Deep and meaningful, the best and original old school rap song about life in the getto.
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66#LongLiveSteelo - Joey Bada$$
Real sad song about the death of capital steez
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67Ashes to Ashley - Sadistik
Lyrics are truly dope and full of meaning! Deserves to be top 10
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68Security - Royce Da 5'9'' Listen to sample

69Jonylah Forever - Lupe Fiasco
Just listen, then decide.

70Accept My Flaws - Dizzy Wright

71Six Feet Deep - Geto Boys Listen to sample

72Dream Forever - Hopsin Listen to sample

73Ballad of Worms - Cage
The only song in the top 10 that deserves to be there is dance with the devil. I guarantee Ballad of Worms is sadder than any of the songs on this list.
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74The Way I Am - Eminem Listen to sample

75Hold On - Rich Homie Quan
This songs about rich homie quans best friend and also mentor who was killed 2 weeks before his album came out, it's from his album I promise I will never stop going in
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76Bad Guy - Eminem Listen to sample

77Dear Old Nicki - Nicki Minaj
How come this isn't on the list? You guys have to listen to this one.
Very very sad song
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78I'll Be Missing You - Puff Daddy
A tribute to The Notorious BIG. The song is very emotional and the chorus made me cry.
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79Like Toy Soldiers - Eminem Listen to sample

80Last Chance - ABK Listen to sample

81How Come - D12 Listen to sample

82Love Comes & Goes - Ed O.G. Listen to sample

83Family Business - Kanye West Listen to sample

84Outta My System - Bow Wow Listen to sample

8516 On Death Row - 2Pac
One of the most underrated songs of tupac, a juvenile narrating his own final demise.
Such a sad song
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86Beautiful Pain - Eminem
One of the saddest Eminem song I've heard...
Super meaningful Eminem song.

letdot52

Listen to sample

87Don't Play This Song - Kid Cudi
This song expresses emotions of humans never told before in such exquisite detail and painstaking reality, this song goes to the depths of cudis mind and brings out his true sorrows within him
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88Leave Me Alone - Tech N9ne Listen to sample

89Sing 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
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90Where'd You Go - Fort Minor Listen to sample

91Mirror - Lil Wayne Listen to sample

92Old Friend - Hopsin Listen to sample

93Write Your Name - Yelawolf Listen to sample

94Take Me Away - Big Scoob Listen to sample

95Fear - Tech N9ne Listen to sample

96The Message - Nas Listen to sample

97I Gave You Power - Nas Listen to sample

98Deja Vu - Eminem Listen to sample

99Life Goes On - 2Pac
This is the saddest song ever made! Makes me so up set

He talks about his own death and how he wants to be buried
Listen to sample

100Stronger Than I Was - Eminem Listen to sample

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This list was created 3 years, 191 days ago and has been voted on over 1,000 times. This top ten list contains 110 items, has been remixed 7 times.

Updated Saturday, August 23, 2014


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