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. :(

These songs might be sad, but Eminem has way to much songs on this list. - RalphBob

V34 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 it's better than hops in it needs to go up at least one if not more so much meaning

Every time I listen to this song I get tears in my eyes when Haley talks to him at the concert in Sweden. It's one of the most emotional songs from Eminem along with Mockingbird that really demonstrate his talent for writing touching lyrics and how much he loves his daughter.

V32 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.

Best story ever told in a rap song

V41 Comments
4Mockingbird - 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...

This song makes me cry every time I hear it, especially when watching the music video. Eminem is amazing, this song is one of my personal favorites of his.

Eminem is energetic in most of his songs but mockingbird was slow and sad and yet is one of the best songs by him

V27 Comments
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

Sad song, but it motivates me to stay strong

V18 Comments
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.

I listen to this every day. It has such a sad tone that you can tell Eminem is having lots of trouble actually saying the words, his voice is trembling in the whole song. It makes me realize how easy we receive life compared to others like Eminem that had to deal with his father leaving and never coming back when he wasn't even a year old, then Eminem dealing with a abusive mother that made him pay for the house bills even though she would kick him out the house, to being beat up by bullies and transporting schools who knows how many times, finally he had to deal with having his daughter Hailie by working extremely hard.

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

This should honestly be number one. If you've never heard it look it up. It hits hard if you ever lost anyone, or just if you have a heart. Can really hear the pain in his voice in this one.

V18 Comments
7My Block - Tupac

I hate how this whole website of full of Eminem fans, it provides a very bias list.

Tupac is the inspiration of Eminem... Tupac was a legend and Eminem is the living legend

Best song ever... Touches your core

I love Tupac and this song is amazing

Yeah eminem isn't the best rapper ever just because he is white tupac and biggie were the best

V5 Comments
8You 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 song is incredibly sad. I could not stop crying, especially since I had a similar experience

V9 Comments
9Good 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

It's a really great song with in depth lyrics that allow you to see a different side of the members of D12.

Really makes you shed a tear man... It should be on the first place..

I wish D12 made more songs like this

V8 Comments
10All I Do - HishaamV1 Comment

The Contenders

11Until the End of Time - 2pac

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

Tupac is the greatest until the end of time
And this song is the greatest until the end of time

V1 Comment
12Headlights - Eminem

I think if you are a true Eminem fan and you know his story there's no way this song wouldn't make you cry... He's been around for so long & in so many of his songs he's shared stories of his childhood and his life that for him to rap about forgiveness towards his mom it's so real and emotional... ONE of my favorite tracks ever... I tear up every time...

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.

I cried more listening to this song when I was 13 then I cried watching Titanic when I was 9. This is song is about how Eminem belies his mom is dying from because of the effects of Emienms lyrics to songs such as 'Cleanin out my closet'. To me this song is closely followed by Stan and Beautiful. If you listen to the lyrics closely in Beautiful you will realize it's very deep and very well written especially the Chorus.

This song makes me cry EVERY time...

V6 Comments
13I'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

It makes me cry every time and I don't even like biggie like that

Very sad song, should be number 1

V3 Comments
14Heather 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

Old friend by hopsin is more real than any of these others. I don't even care much for rap but couldn't stop the leak before the end of the song

V4 Comments
15The Pain - Murs
16Brenda's Got a Baby - Tupac

Talks about the issues of an individual, in this case Brenda, and relates it to a wider social problem across ghettos that communities face. Really eye-opening, especially if you're of the type that blame an individual's failures on that one person, rather than regarding the circumstances they were born into

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.

Beautiful song

V6 Comments
17Rock 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

Sad song about Eminem's struggle

V8 Comments
18Many Men (Wish Death) - 50 Cent

Sad since its true about how he got shot

V2 Comments
19I Tried - Bone-Thugs-N-Harmony

I love bone thugs n harmony even though it's an oldie song in my eyes it means more to me and I'm 11 years old

I can't believe "that crossroads" isn't in top ten! This list is wrong as hell!

20Legacy - Eminem

A song about Eminem's struggle.. makes every true fan going through bad times.. cry

Amazing song, reaches deep into my soul every time I listen to it.

A song about his struggle as a kid to where he is now, sad song

V2 Comments
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List StatsUpdated 27 Sep 2016

3,000 votes
160 listings
5 years, 227 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. Fear - Tech N9ne
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