Top 10 Saddest Hip Hop and Rap Songs

Sometimes, the most powerful emotions find their voice in hip hop and rap. We're talking about those tunes that hit you straight in the heart, songs that speak the raw language of loss, heartbreak, and struggle. They make you think, they make you feel understood, even when you're in the depths of sadness.

Have you ever been moved to tears by a verse? Felt a lump in your throat when the beat drops and a rapper pours their soul into the mic? If so, you know the power of a truly sad hip hop song. The best ones become the soundtrack to our deepest moments, mirroring our own experiences in heartbreaking detail.
The Top Ten
1 Stan - Eminem

Eminem has been my favorite rapper since I was young. Everything he raps about touches my heart. What I really realized about Eminem is that he does not rap about money, style, or fame but all he does is to rap about life, the struggle that people have, pain people experience, and the gain of success in other people's lives. I like Shady's song but more especially, my favorite song is Hallie. The way he raps about Hallie, I feel like she's my own daughter.

This post is from Anele Mangcotywa from South Africa, the country of the rainbow nation.

Eminem (Marshall Bruce Mathers), keep doing it. You're the best of all times.

2 I'll Be Missing You - Puff Daddy

This made me stop and think about what all these rappers have been through. Eazy-E with HIV-AIDS, Tupac and Biggie shot to death, it just hit me. All of these rappers, I have much respect for.

Great song. This song is way sadder than Stan. Stan is about a made-up character, but this song came from the death of Notorious B.I.G., one of Puff Daddy's best friends.

Everything about this song is emotional: the lyrics, the beat, the sound of pain in his voice, and especially the chorus. This song deserves to be number 1.

3 When I'm Gone - Eminem

I would have never ever thought that this song would make me cry. I've listened to many emotional songs, but this one is the only one that makes me cry even if I can't relate. Just not being around a loved one is emotional sometimes, but to be gone trying to support your family and having to travel without seeing your kids is very emotional.

Every time I listen to this song, I get tears in my eyes when Hailie 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.

4 Dance with the Devil - Immortal Technique

The only reason this isn't number one is that 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 ever has before. You Never Know is another amazingly sad song by Immortal Technique, which I would put at number 2.

There is really too much I can say about this song that will take up tons of space, but I'll just say this: it's an EPIC song that if you haven't heard, you NEED to hear. Even if you don't agree with the subject matter, the execution of this story can hook you in just before the first chorus.

5 Dance - Nas

This song will always mean so much to me! I do have a mother, but I can only imagine the pain, and Nas made this song so good!

Damn, when I heard this song, I was speechless. I recently lost a person I loved, and this song opened me up.

It's such a sad song and deserves to be higher. It's about how much he wishes to see his mom again who died and talks about what he remembers about her. He sings the verse himself, making it sound realer.

6 Mockingbird - 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 still cried at night for my mom. He would tell me Jimmy's gonna be alright. This song should be in the top ten.

The most emotional part is when he says he can't afford Christmas presents for his daughters. It's emotional, and seeing this now, when this whole pandemic makes it very sensitive to listen to.

All the longings of a separated father and a daughter more than justified. A beautiful rap, I remember my dad every time I listen to this. It is partially applicable to my life.

7 Difficult - Eminem

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 throughout the whole song. It makes me realize how easy we receive life compared to others like Eminem, who had to deal with his father leaving and never coming back when he wasn't even a year old. Then, Eminem dealing with an abusive mother who made him pay for the house bills even though she would kick him out of the house, to being beaten up by bullies and transferring schools who knows how many times. Finally, he had to deal with having his daughter Hailie by working extremely hard.

8 Dear Mama - 2Pac

What? It's the greatest rap song of all time by the greatest rapper of all time. I like Eminem, but there's a lot of his young fans on this website. Even they voted for him for the best rapper. Now he's the 1st, and he's above 2Pac. Eminem knows that Pac is the greatest, and he said it before. That's why I got much love for him.

It's the most moving rap song of all time. Plain and simple. It is also one of the best rap songs of all time.

2Pac's tribute to his mama really makes me feel emotional. It's a great song with powerful lyrics.

9 Brenda's Got a Baby - 2Pac

"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.

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.

10 Beautiful - 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 is great as well as Em's quote at the end: "God gave you those 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 anyone tell you, you ain't beautiful."

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.

The Contenders
11 Suicidal Thoughts - Notorious B.I.G.

This is one of my go-to songs when I'm severely depressed (I'm Sorry by Joyner Lucas and Broken by Lund are the other two). It makes me just get all of my emotions out. I listen to this because it's stopped me quite a few times from going too far.

This is real talk right here with the lyrics. It still gives me chills years later.

This song is really relatable and it really helps me.

12 Happy Birthday - Flipsyde

The song is touching. Abortion is just as mentally deteriorating for would-be fathers, and it's great to hear a song from a would-be father's point of view. A really good song.

Talking about his baby who he never got to see because his girl had a miscarriage. Love Slim Shady, but this has got to be one.

This song is about a man who paid for his baby mama's abortion and how much he regrets it.

13 Changes - 2pac

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.

Tupac talks of hope, in a tone of hopelessness. The juxtaposition of these two emotions makes for a beautiful song.

This deserves to be in the top 10. It is about what he has been through, and he just wanted peace.

14 My Life - The Game

This song should be number one. My Life by The Game packs so much behind it. It's absolutely amazing.

Can't believe this song wasn't on the list yet. It's sad, but it is so much like my past was. It brings tears to my eyes every time.

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.

15 Like Toy Soldiers - Eminem

The chorus and starting of the song is very emotional for me. I was surprised because it should at least be in the top 20.

This should be much higher, higher than all the other Eminem songs on here. I've cried a few times to this.

It's about how Bugz died because of rap beef. Em feels responsible. Fun fact: Proof portrays Bugz in the video and is later killed.

16 Runaway Love - Ludacris

I can't remove this song, plus Brenda Got a Baby, from my playlist. This is what I always see in the community.

I can always listen to this song. It helps me clear my head. It is so touching.

This song hurts my feelings. I cried the first time I listened to it.

17 Thank You - Xzibit
18 Good Die Young - D12

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

I can't listen to Kuniva's verse without starting to tear up. When he raps, you just feel what he's saying so deeply.

This song really makes you shed a tear, man. It should be in the first place.

19 Kurt Kobain - Proof

One of the best rappers that's existed, but because he's so underrated, nobody listens to him anymore. This an amazing song written by him.

Very underrated song and beat. Anyone never knew this would drop almost a year before Proof got murdered.

This is almost like a suicide note, and it's really sad. It's almost like he knew he was going to get shot.

20 Love the Way You Lie - Eminem

I am a ferocious Stan, but this shouldn't be here. Honestly!

This sucks. Stop worshiping and spamming Eminem on every list!

21 Slippin' - DMX

DMX talks about his mom beating him, being left by his dad, drug addiction, and a lot of other stuff. I don't care what anyone says, best of all time.

Makes me sad every time I listen, knowing he died recently. This song tells about his rough past and how he chased his dream. Long live X.

22 You Never Know - Immortal Technique

It's a beautiful, unconventional track about him falling in love with a girl. What makes it stand out from the usual love song is that he never engages with her sexually, never makes a move, or pushes her to do anything. It's refreshing to hear a track that isn't full to the gills with misogyny. It's a one-of-a-kind song. Immortal Technique definitely knows how to make fire.

Immortal Technique is unique in the rap game. He raps about real-life issues and politics, not just words that rhyme like a skilled Dr. Seuss that make no sense or only rap about sex, drugs, and money. Most rappers are materialistic and have the biggest egos. This is the reason I don't like rap. Immortal Technique changed that for me.

23 Breathin' - T-Rock
24 My Block - 2Pac

This is the best song ever. It touches your core.

25 I Seen a Man Die - Scarface
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