51 Best Sad Rap Songs (Depressing Hip Hop Tracks) Of All Time

Traditionally, rap/hip hop songs have always had many different themes in the lyrics. They are typically associated with violence, gangs, drugs and women. However, this trend is not always the case as many rappers are embracing sad songs about pain, loss and depression. In this article, we will explore the 51 best sad rap songs of all time:

1. Dance with the Devil – Immortal Technique

Dance With The Devil - Immortal Technique

This song narrates the tale of a teenager who joins a gang and starts selling drugs. To prove himself to the gang, he is required to lead his crew in attacking an older woman. The gang waylays and attacks an older woman and does even worse things to her. After this, he realizes that the woman they had just attacked was his mother. This realization is too painful for the teenager, and he opts to commit suicide to escape the pain.

Next: The best songs about suicide of all time (a list of our top picks)

2. Keisha’s Song – Kendrick Lamar

Keisha's Song (Her Pain)

Keisha’s Song is one of Kendrick Lamar’s saddest songs. The song tells the true story of his childhood friend who turned to prostitution to survive. Keisha, the girl in the song, enters prostitution because of the trauma of sexual molestation as a young girl at the hands of her mother’s friend. Keisha eventually turns up dead in the street, stabbed and left for dead. This song is somber because Keisha was only 17 at her death. A young, innocent girl, murdered at the hands of a merciless pervert.

Next: The absolute best sad songs of all time (a list of the saddest tracks ever)

3. Jocelyn Flores – XXXTentacion

XXXTENTACION - Jocelyn Flores (Lyrics)

In this song, XXXTentacion commemorates the life of Jocelyn Amparo Flores. XXX Tentacion met Flores while on vacation in Florida. Shortly after they had met, Flores committed suicide and was found dead in her hotel room. Through this song, Tentacion expresses his sadness for the girl’s death while highlighting the need for better mental health.

Next: The saddest love songs of all time (sad romance tracks)

4. Beautiful – Eminem

This song was released in 2009 in the album Relapse. Beautiful is a heartfelt song in which Eminem talks about his life and all the challenges he has faced to get where he is. Eminem talks of feeling depressed and distancing himself from people in the song. Eminem’s songs are usually aggressive and gritty, but he lays bare his emotions in this song, making his audience appreciate the man, not just the celebrity.

Next: The best songs about depression ever made (a list of our top tracks)

5. I Fall Apart – Post Malone

Post Malone – I Fall Apart (Lyrics) 🎵

Post Malone sings about a bad breakup with a romantic partner in a raw display of emotion. In the song, he talks about the separation’s toll on him, stating that he fell apart due to the breakup. He also speaks of having scars as a result of the split up. As a song about love, this song is relatable to some of us and is one of the saddest songs by Post Malone.

Next: The best songs about a breakup of all time (a list of our picks)

6. This can’t Be Life – Jay Z, Beanie Sigel and Scarface

Jay-Z - This Can't Be Life (feat. Beanie Sigel & Scarface) (Extended Version)

This Can’t Be Life talks about life in the hood. Jay Z talks about daily struggles such as the chances of getting shot on the streets, struggling to provide for your family while also trying to succeed in life. Additionally, Jay Z talks about the loss of his child through a miscarriage. He insists that ‘This can’t be life’ and he has to get out of the hood to a better life. This song resonates personally with anyone working hard every day to improve their lives.

Next: The best songs about life of all time (a list of our picks)

7. Suicidal Thoughts – Notorious BIG

The Notorious B.I.G. - Suicidal Thoughts (Official Audio)

This song is one of the saddest hip hop songs ever. Biggie calls his close friend because he has had depressing and suicidal thoughts in the song. The rapper talks about wanting to commit suicide and unleashing his demons. The song is both sad and angry as Notorious BIG vents his frustrations and eventually commits suicide to the disdain of his friend on the line.

Next: The best songs of all time (a list of the most famous and impactful tracks ever)

8. Brenda’s got a Baby – 2Pac

2Pac - Brenda's Got A Baby

In this song, Tupac talks about a young girl named Brenda who got pregnant after being sexually assaulted. To avoid stigma and shame, she keeps her pregnancy secret. She gives birth to a baby boy in the bathroom of an abandoned house and dumps the baby in the trash. Brenda is, however, forced to take care of the baby, and without the support of her family, the 12-year-old turns to selling drugs to fulfil her needs. Through this song, 2Pac highlights the consequences of teenage pregnancies on society while calling for action.

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9. When I’m Gone – Eminem

Eminem - When I'm Gone (Official Music Video)

Here Eminem talks about his strained relationship with his daughter. He acknowledges that his failed marriage and music career has aggravated the relationship between the two. He is, however, insistent that he works hard on his music to give his daughter a better life than he did. Additionally, he promises to do better as a father. This song will reach the depths of your soul, especially if you are a parent struggling to raise your child.

Next: The best songs about daughters of all time (a list of our favorites)

10. Slippin’ – DMX

DMX is traditionally known for party bangers but he takes a more emotional tone in this song. He talks about his struggle as a kid encouraging others in a situation similar to his to find meaning in suffering. He also talks about his battle with drug and substance abuse, including when he almost died from an overdose. Despite ‘slippin’ into drug abuse, and problems with the law, he insists that he must get up and better his life, especially after getting a son.

Next: The best songs about drugs of all time (our list)

11. Death Enclaimed – Youngboy Never Broke Again

nba youngboy - death enclaimed

This is one of the most touching songs by a more modern artist. In this song, Youngboy Never Broke Again talks about his most intimate fears. Particularly, he talks of his fear of being killed, which is common among rappers. He also expresses his fear of fake friends and fake love. Fears which have prevented him from finding real love.

Recommended: Songs about fake friends

12. Suicidal (Remix) – YNW Melly, and Juice WRLD

YNW Melly - Suicidal Remix (Lyrics) ft. Juice WRLD

This is one of the most relatable songs to contemporary teenagers. In this remix, YNW Melly and Juice WRLD talk about the same fears and problems that modern young people are having, hurtful breakups. The song talks about a bad breakup that leaves him in distress. The pain drives him to take pills, drink alcohol and contemplate suicide.

Next: The best hip hop songs of all time

13. I Feel like Dying – Lil Wayne

Lil Wayne - I Feel Like Dying

I Feel Like Dying is a sad song in which Lil Wayne expresses his feelings of despair by talking about how he feels like dying, and he talks about how drug addictions can force you to go to extreme lengths, including the cost of your life.

Next: The best songs about addictions of all time (our list)

14. Life’s A Mess – Juice Wrld ft. Halsey

Juice WRLD ft. Halsey - Life's A Mess (Official Visualizer)

In this song, Juice Wrld and Halsey acknowledge that sometimes life can be hard. Specifically, they talk about the pain of losing somebody you loved and hoped to be with forever. While such pains make life hard, they encourage that we learn to love and move on regardless.

Next: Greatest rappers in history (our list)

15. Lip Peep – Hellboy

Lil Peep - hellboy (Official Audio)

Hellboy talks about his love for a girl not available to him in a more upbeat approach. He speaks of his struggle and how he tries to rationalize his feelings. In this depressing tune, he speaks of the pain of loving someone you could never have.

16. Colored Dreams – Reason

REASON - Colored Dreams

This masterpiece tells the story of a prisoner sentenced to murder. The prisoner sees the pain he caused through his actions and is apologetic for his actions. He admits that he committed the crime to appear ‘gangster’ without thinking of the consequences of his actions. The pain of his actions overwhelms the prisoner, and he commits suicide in his cell.

Next: The best songs about hurting and deep pain of all time

17. Sing about Me, I’m Dying of Thirst – Kendrick Lamar

Kendrick Lamar - Sing About Me, I'm Dying Of Thirst

This song is one of the most popular songs in the world. It has been featured in numerous movies, and TV shows. The first part of the song, Sing About Me, tells the story of his friend who was a victim of gun violence. In the second part of the song, Dying of Thirst, Kendrick Lamar talks about the impact of Keisha’s song on her sister.

18. You Never Know – Immortal Technique

You Never Know - Immortal Technique (Dir. Al Mukadam)

Immortal Technique tells the story of his platonic relationship with a girl he knew. The girl changed his life for the better, encouraging him to read and avoid the streets. Eventually, he tells the girl of his feelings for her, but she weeps and leaves.

19. All That I Got Is You – Ghostface Killah ft. Mary J. Blige

Ghostface Killah - All That I Got Is You (Official HD Video) ft. Mary J. Blige

This song is one of the most emotional rap songs ever made. Ghostface tells the story of his life. Specifically, he talks about his childhood, growing up hustling amongst the streets and how he was forced to live without hope. He also pays tribute to his mother, who raised him despite the struggles.

Next: The best funeral songs for mom of all time (a list of our picks)

20. Six Feet Deep – Geto Boys

Geto Boys - 6 Feet Deep (Official Video)

Released in 2013, the song expresses the pain of losing a friend or group member after they were gunned down. The group promises to remember their dead friends and family and pay them respect despite being dead.

Next: The best songs about respect of all time

21. Song Cry – Jay Z

Jay Z talks about the end of his long-term relationship because of his mistakes. While he understands why his partner wants to leave, he is hurt that this is the end, and he has to live with his mistakes forever.

Next: The top hip hop songs of the 2000s (’00s rap songs list)

22. Stan – Eminem

Eminem - Stan (Long Version) ft. Dido

One of the most legendary songs by Eminem, Stan, is a story about an obsessive fan who writes to Eminem to meet him. The fan writes over ten letters explaining how he is lonely and in love and wishes to be with Eminem. The fan eventually kills himself and his pregnant girlfriend after not receiving a response from Eminem.

Next: The best songs about feeling alone and loneliness ever made

23. Robbery – Juice WRLD

Juice WRLD - Robbery (Directed by Cole Bennett)

Juice WRLD talks about his attempts to find love. He follows his father’s advice not to show his insecurities to women and therefore dresses in expensive attires and jewelry to impress girls. Girls tell him to avoid falling in love lest he gets hurt, but as the hopeless romantic, he falls in love and gets heartbroken.

Next: Top Juice WRLD songs of all time

24. Calling my Phone – Lil Tjay feat 6Lack

Lil Tjay - Calling My Phone (feat. 6LACK) [Official Video]

Lil Tjay and 6Lack talk about obsessive exes who cannot move on. The exes are constantly calling to say they miss him and what they had. However, both are insistent that they have moved on and ask to be left alone.

25. I’ll Be Missing You – Puff Daddy Faith Evans featuring 112

Puff Daddy [feat. Faith Evans & 112] - I'll Be Missing You (Official Music Video)

This song is about a man who is left heartbroken by the death of his friend. He talks about how he will always miss his partner and never forget him. The friend referred to in this song is Notorious BIG, a friend of Diddy who was murdered.

Next: The best friendship songs for best friends (ever made)

26. Long Gone (Save Me from This Hell) – $uicideboy$

Long Gone (Save Me from This Hell)

This song talks about a person who frequently abuses drugs to escape the pain of losing friends. He wants to die to escape living which to him is hell.

27. Tearz – Wu-Tang Clan

Wu-Tang Clan - Tearz (Official Audio)

Wu-Tang tells two sad stories within this song. The first part of the song talks about the loss of a younger brother who got gunned down in the street, while the second part talks about Mo, who contracts HIV and dies.

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28. Changes – 2Pac

2Pac - Changes ft. Talent

Tupac calls for societal change in this song. He insists that there was no change despite the efforts of civil rights movements. Racism, police brutality, drugs and poverty persist among the African-American community, and Tupac calls for change to correct this situation.

Next: The best songs for women empowerment of all time (a list of our picks)

29. Dear mama – 2Pac

Tupac tells the story of his childhood and how he grew up in a single-parent family. Despite his humble beginnings, he grew up and achieved success in the music industry. He thanks his mother for her efforts and sacrifices to achieve such greatness.

30. Broken Love – Mo3 & Kevin Gates

Mo3 & Kevin Gates - Broken Love (Official Video)

Kevin Gates talks about how difficult his life was growing up. He talks about the things his mother underwent to provide for him. He also comments on fake friends and women in his life.

Next: The top songs about growing up of all time (our list of picks)

31. 4 Your Eyes Only – J Cole

J. Cole - 4 Your Eyes Only [Explicit]

This song pays tribute to a childhood friend of J. Cole. The song highlights various social issues such as gun violence, fatherhood and mass incarceration. Cole is saddened that while he gets to live and raise his children, his friend dies and misses out on his daughter’s life.

Next: The best J Cole songs

32. Dead Homiez – Ice Cube

Ice Cube - Dead Homiez

Ice Cube talks about the life and death of his close friend. Ice Cube never got to say goodbye to his friend who was shot dead in a robbery gone wrong.

Next: The top fast rap songs ever recorded

33. Last Good Sleep – Company Flow

Last Good Sleep - Company Flow

This song talks about his feelings about his step-father. The rapper speaks about his step-father getting drunk and fighting with his mother while he tries to shut his ears to escape the fights.

34. Love Scars – Trippie Redd

Trippie Redd - "Love Scars" Official Music Video | Pigeons & Planes Premiere

This track is about a woman from the neighbourhood he grew up in. The woman is, however, not committed to their relationship, and as a result, they break up, and Trippie Red is left with scars, Love Scars.

35. Keep Livin – Jean Grae

Jean Grae "Keep Livin" [Official Audio]

Jean Grae talks about people who have lost hope and joy in living. To avoid the pain of living, they escape through smoking, drinking and other drugs. Jean Grae, however, challenges this kind of life, encouraging them to keep living despite it all.

36. Smile to Keep from Crying – Boosie Badazz

Boosie Badazz "Smile To Keep From Crying" (WSHH Exclusive - Official Music Video)

Boosie Badazz talks about losing his three aunts within one year, losing a friend to gun violence and the betrayal he felt after his girl didn’t write to him while in prison. All he can do is smile to keep from crying.

37. Acid Rain – Chance the Rapper

Chance The Rapper - Acid Rain

Chance the Rapper talks about his childhood and his life in general. He talks about the fear that his ‘bars’ are not very good and his feelings towards his mother asking to quit music and go back to school. He is reminiscent of the shows he used to do in senior year.

38. The Heart & the Tongue – Chance the Rapper

Chance The Rapper - The Heart & The Tongue (2021) | [Official Music Video]

In this piece, Chance the Rapper talks about a man with an internal conflict. He is caught up in a hard decision indicated by the metaphor of a heart and mind in battle.

39. Perkys Calling – Future

In this track, Future reveals his battle with addiction and how a life of fame and success has left him feeling depressed and suicidal.

40. We Ball – Meek Mill and Young Thug

Meek Mill - We Ball feat. Young Thug (Official Video)

Meek Mill and Young Thug talk about the pain of losing friends to gun violence. In the opening, Meek Mill pays tribute to three of his friends that were murdered. He says that the pain of these losses may be why he is always taking drugs.

41. They Reminisce Over You (T.R.O.Y.) – Pete Rock & CL Smooth

Pete Rock & CL Smooth - They Reminisce Over You (T.R.O.Y.) (Official Video)

Pete Rock and CL smooth pay tribute to a young friend who died in their youth. They reminisce on the good times with him and how his death affected them.

42. Stray Bullet – Organized Konfusion

Organized Konfusion - Stray Bullet

This timeless classic highlights the effect of gun violence in the hood from the perspective of a bullet. Some of the details are graphic as so many people are left dead on the street.

43. Dance – Nas

Dance pays tribute to Nas’ dead mother. Nas remembers all the good times with his mother and wishes he could get one more chance to dance with her.

Next: The best funeral songs of all time (a list of our picks to choose)

44. Kim – Eminem

Eminem raps about a murderous end to a relationship with Kim, the two fell in love at a young age and had a daughter. They, however, split up, and Kim gets married to another man. In a fit of anger, the jilted lover kills the new man, his son, and then Kim.

Next: The best songs about jealousy of all time (our list of favorites)

45. Downtown – August Alsina ft. Kidd Kidd

August Alsina - Downtown ft. Kidd Kidd (Official Video)

August Alsina talks about the struggle to survive in the streets and jail in this song. He talks about the struggle to find young women on the street, young men being gunned down and trying to escape the police.

46. Millie Pulled a Pistol on Santa – De La Soul

De La Soul Millie Pulled A Pistol On Santa

De La Soul talks about the life of a young girl, Millie, who was sexually assaulted by her father. Millie’s father worked as Santa in a local store while society was unaware of him assaulting his daughter. Fed up with this kind of life, Millie pulls a pistol on her father and finally ends the demon that tormented her life.

47. Ballad of Worms – Cage

Cage - Ballad of Worms

Cage tells the story of how he loved a beautiful girl who is barely alive after being ravaged by meningitis. He blames God for the injustice of giving him a beautiful girl only to let her die in misery.

48. The Message – Dr. Dre, Mary J. Blige

Dr. Dre - The Message (feat. Mary J Blige)

In this track, Dr Dre sends a message to God, complaining about the pain of losing people in his life. He feels that it is an injustice for two people to connect, only for one to be taken away by death.

49. Renee – Lost Boyz

Lost Boyz - Renee (Official Video) [Explicit]

This song is a love story about a girl called Renee. The song tells how they met and courted, creating a friendship that blossomed into love. Their love, however, ends in tragedy after Renee is gunned down in the street.

Next: The best hip hop love and romance songs of all time

50. Da Art of Storytellin’ – OutKast

Outkast - Da Art of Storytellin' (Part 1) (Official Video)

This song tells the story of two female characters who devolve to prostitution to survive. The saddest story in the song is that of Sasha, who is found dead with a needle in her hand, barely two months before the day she would have given birth.

51. Retrospect for Life – Common and Lauryn Hill

Common - Retrospect For Life (Official Video) ft. Lauryn Hill

Common contemplates aborting his child through this lyrical masterpiece after his girlfriend gets accidentally pregnant. Throughout the song, Common evaluates the potential consequences of his actions and eventually decides to keep the pregnancy and watch his child grow.

If you are an ardent lover of sad hip hop songs, then you will love these songs. They tell painful gut-wrenching stories that will move you to your core while also opening your eyes to some of the challenges facing the society.

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