Saddest Rap Songs


Don't agree with the list? Vote for an existing item you think should be ranked higher or if you are a logged in, add a new item for others to vote on or create your own version of this list.

The Top Ten

Stan - Eminem
One of eminem's best! And it's sad too. So much meaning here. This song deserves number1


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. :(
[Newest]I used to do online gaming and I fell in love with this one kid who always played this song and it reminds me of him... :(

2When 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
[Newest]7 out of 10 songs on the top ten is Eminem... coincidence? I think not.

3Mockingbird - 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
[Newest]I cry every time it's all about his life and Not afraid (reversed) tells the story of how the illuminati tried to control the way he lived

4Dance 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.
[Newest]Better than anything Eminem's ever made

5Beautiful - 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

6Difficult - 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.
This is definitely the saddest song by Eminem if not any rapper. I'm a diehard Eminem fan and when I heard this song it blew my mind at the amount of emotion and love he puts in this song for his friend. RIP Proof
[Newest]This is probably the only song that could ever make me cry

7Good Die Young - D12
The good really do die young Pac, biggie, bugz and proof R.I. P


The best sad song ever! R.I.P.. :(
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
[Newest]Thi should be in top 4

8Brenda's Got a Baby - Tupac
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.
Already shocked by this song

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
[Newest]Hopsin will save hip-hop

10Hailie's Song - Eminem

The Contenders

11You 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
[Newest]Immortal technique in general touches the heart all his songs have strong meanings.

12My Block - Tupac
I hate how this whole website of full of Eminem fans, it provides a very bias list.
I hate that you don't see that statement was based. if you choose to disregard Eminem then that's your loss, don't push your insecurities onto us.
Tupac all the way he is better then Eminem any day
Lovely song and deep

13Kurt Kobain - Proof
The deepest personal confession of the greatest man to never see his true potential.
Just Connects, must listen

14The 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.
I don't hate Eminem. I hate his dickriding fans.

15I'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

16All That I Got Is You - Ghostface Killah
Seriously, number 12? Ghost's childhood was way harder then Em's.

17Until the End of Time - 2pac
Glad it's in top ten:) Tupac is the best rapper of all time.

18All I Do - Hishaam

19Dead 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.


Best one on this list.

20I Miss My Homies - Master P

21Time After Time - Kid Ink
Listen to this it makes me think about my ex

22Rock 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
[Newest]Just listen to it and you'll get very depressed for a few minutes. (Or that's what I had)

23Sing for the Moment - Eminem

24Many Men (Wish Death) - 50 Cent

25The Pain - Murs

26One Day - UGK

27Slippin' - DMX

28Legacy - Eminem
A song about Eminem's struggle.. makes every true fan going through bad times.. cry
Best sad song ever

29Tearz - Wu Tang Clan

30Dance - Nas

31Norm Ender - Son Uyku

32Soundtrack 2 My Life - Kid Cudi

33Headlights - Eminem
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.
Eminem forgave his mom after all she did to him to the lyrics are so good and sad
How is this not number one?! It is the saddest song ever. If you now anything about Eminem, you know how hard it must have been to forgive her.

34The Message - Nas

35Careful What You Wish For - Eminem
A really sad Eminem song about fame and drugs.

36Too Deep for the Intro - J. Cole

37Hands 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

38See 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.


39My 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.
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

40Suicidal Thoughts - The Notorious B.I.G.

41Do Bad On My Own - Z-Ro
A song about loneliness, sadness, betrayal, and suicide.

42Beautiful Pain - Eminem
Super meaningful Eminem song.


One of the saddest Eminem song I've heard...

43The Book of Soul - Ab-Soul
Really deep song about ab's girlfreind of 7 years commiting scuicide

44Ill Mind of Hopsin 6 - Hopsin
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 sad than Heather Nicole, I think this deserves to be in the top 10
[Newest]Saddest song by the realest rapper

45The 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.

46Hold Ya Head - The Notorious B.I.G. & Bob Marley
Remix of suicidal thoughts

47So Hard to Breathe - B.o.B

48Wicked Games - The Weeknd

49If I Had - Eminem
It is nice... sad... at all if you listen to it with high volume it will make you berserk... love it...

50One Life - The Last Emperor ft. Too Poetic & Esthero

51Otherside - 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!

52Watch How It Go Down - Termanology

53Live 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.

54You Got Me - The Roots

55Happy Birthday - Flipsyde
This song that reminds me on sad times...

56Crew Love - Drake

57Kenji - 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.

58Dream Forever - Hopsin
This song is the perfect song for a hopeless romantic just wishing life was as good as their dreams

59Like Toy Soldiers - Eminem
This song is great, but is so much better once you know the whole story behind it (Google helps)

60No More - Will Smith

61Airplanes, 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.

62Choices (A Wave For Alex) - Charles Hamilton

63November - Sadistik
This is such a good song should be top 20 at least

64Last 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.

65The 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)

66Rebecca - Grieves
Really great song. You should give it a listen
Such a good song

67Letter to My Father - Caskey

68Life Goes On - 2Pac
This song is amazing. It's hard for me to hold back tears when I listen to it. This is the first Tupac song I ever heard and I've been hooked on his music ever since.
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

69Why - Nate Dogg
I can't find this song

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

70Same Love - Macklemore
How is this also not on the list.

71Family Business - Kanye West

72Goodbye - 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.

73The Message - Grandmaster Flash & The Furious Five
Deep and meaningful, the best and original old school rap song about life in the getto.

74#LongLiveSteelo - Joey Bada$$
Real sad song about the death of capital steez

75Ashes to Ashley - Sadistik
Lyrics are truly dope and full of meaning! Deserves to be top 10

76Security - Royce Da 5'9''

77Jonylah Forever - Lupe Fiasco
Just listen, then decide.

78Accept My Flaws - Dizzy Wright

79Six Feet Deep - Geto Boys

80Ballad 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.

81The Way I Am - Eminem

82Hold 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

83Bad Guy - Eminem

84Dear Old Nicki - Nicki Minaj
How come this isn't on the list? You guys have to listen to this one.
Very very sad song

85Old Friend - Hopsin
One off the saddest songs I've ever heard.

86Crank That - Soulja Boy
It's sad because it exists.

87Biggie Smalls vs Kanye West - Suicidal Thoughts
Its probably the best you can get should be top 10
Why isn't this #1? What?!

88Last Chance - ABK

89How Come - D12

90Love Comes & Goes - Ed O.G.

91Outta My System - Bow Wow

9216 On Death Row - 2Pac
One of the most underrated songs of tupac, a juvenile narrating his own final demise.
Such a sad song

93Don'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

94Leave Me Alone - Tech N9ne

95Sing 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.
Oh my god this is amazing

96Where'd You Go - Fort Minor
An amazing sad song about a veteran returning home from war belongs in the top 15 songs but there are too many fans riding Eminems D_ck so his songs got top 10 even though some of them are not even sad.

97Write Your Name - Yelawolf

98Take Me Away - Big Scoob

99Fear - Tech N9ne

100I Gave You Power - Nas

Comments About This List

Featured Lists
Popular Lists
New Lists

Top Remixes of This List






see more...

Posts About This List

List Info

This list was created 4 years, 70 days ago and has been voted on over 2,000 times. This top ten list contains 123 items, has been remixed 9 times.

Updated Friday, April 24, 2015

List Error Reporting

See an item on this list that's misspelled, duplicated, or doesn't belong? Let us know. Click here to report the error.