Saddest Rap Songs

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The Top TenXW

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. :(

This song gives you a feeling of regret.. Eminem is adjusting to his fame and in this song it sort of relates to himself in a way. Stan is almost like a second slim shady.

V25 Comments
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

7 out of 10 songs on the top ten is Eminem... coincidence? I think not.

V20 Comments
3Dance 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.

The story behind this is amazing.

V28 Comments
4Difficult - 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

Proof rest in peace

V14 Comments
5Mockingbird - 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

I can relate to this song so much because my dad left because my mom was insane

V18 Comments
6Beautiful - 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

I listened to this the day my mom died and do every time another year goes by love you mom R.I.P. 10-27-09

V16 Comments
7Good Die Young - D12

The good really do die young Pac, biggie, bugz and proof R.I. P - Norrisofchuck

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

Thi should be in top 4

V11 Comments
8Heather 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

Hopsin will save hip-hop

V5 Comments
9I'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

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.

Immortal technique in general touches the heart all his songs have strong meanings.

This should be in 4th place

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The Newcomers

?A Wonderful Life - T.I
?Baby Don't Cut - Bmike
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The Contenders

11My 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

12Rock 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

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

V8 Comments
13Kurt Kobain - Proof

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

Just Connects, must listen

14Brenda'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

This is one of my favorite Tupac songs because of how well he describes Brenda and her awful plight

V7 Comments
15Until the End of Time - 2pac

Glad it's in top ten:) Tupac is the best rapper of all time.

16All I Do - Hishaam
17Sing for the Moment - Eminem
18Headlights - 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.

Saddest Eminem song there is. Just watch the music video. - letdot52

V4 Comments
19The Pain - Murs
20Changes - 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.

I cried when I first heard this song.

Tupac is still and forever a legend peace to my homie

V4 Comments
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List StatsUpdated 4 Sep 2015

2,000 votes
134 listings
4 years, 203 days old

Top Remixes (12)

1. Beautiful - Eminem
2. Mockingbird - Eminem
3. See My Tears - MGK
Duggo38
1. My Block - Tupac
2. All I Do - Hishaam
3. Until the End of Time - 2pac
cleff
1. Stan - Eminem
2. When I'm Gone - Eminem
3. Mockingbird - Eminem
Ajkloth

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