Think rap is only about bragging?
A lot of bad rap music is. That’s true.
But good rap talks about social issues, philosophy, aspiration and much more.
And yes, some rap music is sad. Very sad.
The best sad rap songs reach right into your chest and touch your heart, the same as any other genre.
If you’ve never been a rap fan, this probably comes as a surprise to you.
You’ll definitely want to keep reading to learn about some of the greatest and saddest rap songs ever made. The styles differ a lot, so there should be something here for everyone.
Table of Contents
- 1 Best Sad Rap Songs
- 1.1 When I’m Gone by Eminem
- 1.2 Gangsta’s Paradise by Coolio
- 1.3 Understand by BoyWithUke
- 1.4 Headlights by Eminem
- 1.5 Pain by Josh A
- 1.6 This Can’t Be Life by Jay Z, Beanie Siegel & Scarface
- 1.7 Suicidal Thoughts (Nuck Chorris Remix) by Notorious B.I.G
- 1.8 Dear Mama by 2Pac Shakur
- 1.9 I Fall Apart by Post Malone
- 1.10 Marvin’s Room by Drake
- 1.11 Undying Love by Nas
- 1.12 You Never Know by Immortal Technique
- 2 Saddest Rap Songs: Final Thoughts
Best Sad Rap Songs
There are actually a lot of sad rap songs out there. Far more than I ever would have guessed. But most of them are pretty terrible. The songs below are the best we could find. These are songs that are actually capable of eliciting real emotion in listeners, as all good art does.
That said, there is one big problem with this list of songs. See if you can see what the problem is. I’ll address it in the conclusion at the end of the article.
When I’m Gone by Eminem
When I’m Gone is a song from Eminem’s fifth studio album, Curtain Call: The Hits, released in 2005. It is a message from a father to his daughter. The father (Eminem himself) is too busy to spend time with his daughter who craves nothing more than to be with her beloved dad.
In a way, the sad song is about Eminem’s rise to fame and how it kept him away from his loved ones. The song portrays Eminem’s guilt and regret for not being there for his daughter. It is a somber rap song that also conveys his fear of losing his kids once he departs this world for good.
Gangsta’s Paradise by Coolio
Gangsta’s Paradise is a rap song by Coolio, released in 1995 as the lead single from his second studio album, Gangsta’s Paradise. It was also featured in the pretty terrible 1995 film Dangerous Minds, starring Michelle Pfeiffer, and went on to win the 1996 Grammy Award for Best Rap Solo Performance.
The song begins with a line from Psalm 23:4 – as I walk through the valley of the shadow of death. The lyrics then describe the rapper’s sad life on the streets and his damaged relationship with his mother. Gangsta’s Paradise resonated with millions of people around the world as it conveys a sense of hopelessness and the harsh realities of life.
Understand by BoyWithUke
BoyWithUke’s Understand is a sad rap song about a boy’s depression. The protagonist has broken up with a girl and he wants her to understand that he has deep-rooted issues which is why he is the way he is. He is also angry and wants to express all of his emotions by writing love songs for the girl he loves.
Understand is not just about heartbreak over a relationship. The protagonist also addresses his younger self or his inner child. He says he has been taking medicine for his depression, which makes him do things he is not proud of. The rap song accurately depicts what millions of people with mental health issues undergo.
Headlights by Eminem
Many Eminem fans believe Headlights to be his saddest song to date. Released in 2013, the talented rapper co-wrote the song with Nate Russ, Luis Resto, Emile Haynie, and Jeff Bhasker.
The singer addresses his mother who is an alcoholic. Both mother and son have been victims of their dad’s physical abuse and their relationship is strained.
Eminem had previously attacked his mom, Debbie Mathers, in several of his rap songs. Through Headlights, he explains why he did so and apologizes to her for those verbal attacks. He later explained in an interview that he used Headlights to do a lot of explaining to his mother and it was a way for him to get a lot of things off his chest.
Pain by Josh A
Hip-hop rapper Josh A’s Pain features relatable lyrics and a haunting melody. It expresses the singer’s raw emotions and struggles with mental health. Many people with depression found the sad rap song highly relatable, since it helped them dive deep into the dark corners of their minds where their darkest emotions lay buried.
The chorus of the song is ‘pain goes by when you don’t think about it’ and it is repeated several times. The singer means that depressed people are often asked to ignore their feelings and pretend that all is well. They are also given medication that does nothing to eliminate the root cause of the pain, but only suppresses it temporarily.
Josh A has been compared to the likes of rap artist Drake and is best known for his 2021 song Best Friends which received millions of views.
This Can’t Be Life by Jay Z, Beanie Siegel & Scarface
This Can’t Be Life is a classic in the rap genre and one of the saddest rap songs depicting the harsh life on the streets. Jay Z released it as a single from his fourth studio album in 2000: The Dynasty: Roc La Familia.
Jay Z talks about his difficult childhood on the streets before he made it big. He tried selling drugs and had to evade gunshots each night. Every time he escaped death, he felt “this can’t be life” and that is the inspiration behind this song. Scarface takes the song to a whole different level. He raps about his son who later saved his (Scarface’s) life by donating a kidney to him.
Suicidal Thoughts (Nuck Chorris Remix) by Notorious B.I.G
Notorious B.I.G released this final track from his 1994 album Ready to Die. In it, he calls Puff Daddy on the phone and explains that he is tired of all his crimes and the lack of love in his life and that he plans to end it.
Throughout the track, Puff Daddy tries to talk B.I.G out of it but the singer nevertheless commits suicide at the end. It should come as no surprise that this track also made our list of songs about suicide and suicidal thoughts.
Real gunshots, telephonic sounds, and the sound of B.I.G.’s body falling to the floor give the rap song a realistic feel and make it even more dramatic and haunting. The rapper also seamlessly weaves this fictional death in Suicidal Thoughts into his next album aptly titled Life After Death.
Dear Mama by 2Pac Shakur
Tupac (2Pac) Shakur was a rapper with many talents: he was brilliant at writing poems, acted in movies, and always spoke up for what he believed in. He was a free thinker and many of his rap songs were about the politics in America. Unfortunately, Tupac died too young, at just 25, after being shot in Las Vegas.
In Dear Mama (album Me Against the World, 1995), Tupac reminisces about his childhood spent in poverty. He and his sister faced many hardships and often blamed their mom for it.
But he admits that it must have been incredibly hard for their mother to raise them. He wonders how she managed to bring them up on welfare and for that, he thanks her and calls her his queen.
Tupac ends the sad rap song by saying that he cannot ever repay his mother for all that she has done for him, but he hopes that she knows he appreciates her greatly.
I Fall Apart by Post Malone
I Fall Apart is a song by Post Malone, released in 2016 as part of his debut studio album, Stoney. The song is considered one of the saddest rap songs due to its melancholy lyrics and haunting tune.
The lyrics of I Fall Apart describe how the singer is literally falling apart after his girlfriend has repeatedly cheated on him. She has now left him and he is devastated.
The song describes the impact of the breakup on his mental and emotional health. Post Malone fans found the themes of infidelity and heartbreak expressed in I Fall Apart highly relatable.
Marvin’s Room by Drake
Canadian rapper Drake’s Marvin’s Room is a sad song about past relationships. The singer reminisces about the beautiful time he had with a girl who has now moved on from their tumultuous relationship and has found love and peace with someone else. He especially thinks of her when he is drunk.
Drake questions why she chose someone else, as he still thinks he is the best choice for her. The song depicts his feelings of regret, jealousy, and not being sure about how fame affects his relationships.
Marvin’s Room became a cultural phenomenon, because it resonated deeply with people who have experienced heartbreak and unrequited love. The best part is that before releasing it as a single, Drake had only posted Marvin’s Room on his brand October’s Very Own blog in 2011. Only after the song became so popular, did he release it as a single in the same month.
Undying Love by Nas
I thought you loved me.
I thought you cared for me.
I thought you believed in me.
That is the chorus of Nas’s Undying Love (album I Am, 1999). The sad rap song will bring tears to your eyes as you listen to its lyrics.
The singer describes how he returns home one day after a gig in another city, only to find his fiancée in the arms of another man. He has been planning on proposing to her with a beautiful ring, but she has given him this shocking surprise instead.
Needless to say, he is angry, hurt, and devastated. In that trauma, he shoots his girlfriend and her lover. As the cops burst in on the murder scene, he says “Now unto God, we elope, we elope” before turning the gun on himself.
You Never Know by Immortal Technique
This beautiful, yet tragic, rap song shows Immortal Technique’s soft side. Tech describes a beautiful Latina girl he is in love with. She is different: focused and disciplined.
He and everyone else believe they have no chance with her. Yet he spends time with her, but never attempts to touch her, since he respects her too much.
Eventually, he is jailed but once he is out, he comes back to search for this girl. Unfortunately, she is dead. She has left a letter for him saying she had HIV and that she got it through a blood transfusion.
She says she loved him deeply and wished she could have given her virginity to him, but could not because of her condition. The message of You Never Know is “never take love for granted as it can be taken away from us.”
Saddest Rap Songs: Final Thoughts
As mentioned above, this list of the best sad rap songs has one big issue. Can you guess what it is?
Every single one of the songs was performed by a male rap artist. There are no females on the list. When I noticed that, I racked my brain to think of a good sad rap song sung by a female, but I couldn’t come up with one.
But there must be one. Actually, there must be many. One problem for me is that I love older rap from the 1980s, 90s, and early 2000s. Back then, there just weren’t very many female rap artists, so there really aren’t that many songs to even choose from.
Maybe you guys can help, especially if you are familiar with newer rap music. There are far more females making it in the industry these days, including many great female rappers. If you know of any sad rap songs sung by a female, please let me know in the comments below.
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