60 Best Sad Rap Songs (Depressing Hip Hop Tracks)

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Written By Will Fenton

Founder of MidderMusic. From numerous bands to stints working in music shops, read more about me on the 'Here's My Story' page!

Rap as a genre began at New York block parties in the early 1970s.

But over the years, many artists recorded sad rap songs about depression, heartbreak, or issues such as gun violence. 

So for today’s article, we picked the 60 best sad rap songs of all time.

Many of them are based on real stories or personal experiences which makes them even more somber. 

Table of Contents

1. “Dance With The Devil” by Immortal Technique

Released in 2001, “Dance With The Devil” remains one of the most impactful rap sad songs.

The song tells a story of a teenager growing up on the street and joining a gang.

Lyrically, it’s probably one of the most depressing rap songs ever written.

2. “Jocelyn Flores” by XXXTENTACION

XXXTENTACION is considered to be a leading name in emo rap.

He was known for making music about depression and alienation.

And one of his signature songs is dedicated to Jocelyn Amparo Flores who commited suicide shortly after she and the singer met. 

3. “Keisha’s Song” by Kendrick Lamar 

“Keisha’s Song” is arguably one of Kendrick Lamar’s saddest songs.

It tells a story of a girl who turned to prostitution to survive and eventually ends up dead at 17.

This song is another proof of how tragic the stories behind rap songs can be.

4. “I Fall Apart” by Post Malone

“I Fall Apart” is one of the sad rap songs about love and breakup.

In essence, it’s about letting go and scars that appear after separating. 

If you’re currently going through a breakup, you might find it relatable.

5. “Love Scars” by Trippie Redd

If you search for the saddest rap songs, you’re probably going to come across “Love Scars” by Trippie Redd.

In a way, it’s a typical modern heartbreak rap song.

6. “Beautiful” by Eminem

Eminem has written many sad rap songs.

But “Beautiful” stands out. 

It’s genuine and powerful, and it talks about Eminem’s depression and all the challenges he faced in life.

7. “Robbery” by Juice WRLD

Juice WRLD was an American rapper known for making somber rap songs about heartbreak.

He was also a leading figure in emo rap and SoundCloud rap genres.

And his track “Robbery” is one his best known songs.

The song is about dealing with failed relationship – he is comparing his heartbreak to a bank robbery.

8. “P2” by Lil Uzi Vert

“P2” by Lil Uzi Vert can also be found on many lists of sad hip hop songs.

It was released in 2020 as a sequel to his single “XO Tour Llif3”, which peaked at number seven on the Billboard Hot 100.

9. “This Can’t Be Life” by Jay-Z and Beanie Sigel

This Can’t Be Life” is a soulful, melancholic rap song about life in the hood.

The song deals with daily struggles on the street and fears of being shot. 

It’s a throwback to Jay-Z’s early music that tackles such difficult topics. 

10. “Suicidal Thoughts” by Notorious BIG 

Notorious BIG’s 1994 track is one of the most memorable rap songs about suicide.

The song is a part of Biggie’s debut studio album “Ready To Die.” 

It talks about suicidal thoughts and the need to talk to someone.

Whenever suicidal thoughts occur, it’s absolutely crucial to share that with someone.

11. “Good News” by Mac Miller

Don’t let the title of this song fool you.

And although it might sound laid-back at first, “Good News” generally talks about loneliness. 

But it’s also a reminder that it’s possible to escape your negative thoughts.

12. “Brenda’s Got A Baby” by 2Pac

In his song “Brenda’s Got A Baby”, 2Pac tackles the problem of teenage pregnancy.

In the song, Brenda is a young girl who gets pregnant and turns to selling drugs. 

This song is yet another proof of 2Pac’s talent and conscious songwriting. 

13. “Save That Shit” by Lil Peep

In his 2017 emo rap song, Lil Peep talks about his relationship problems.

He was a leading figure in 2010s emo rap scene, but as is the case with many hip hop artists, his life and career ended way too early.

14. “Slippin’” by DMX

An artist that had a huge impact on 2000s rap is DMX.

ALthough he was also known for making party bangers, his song “Slippin’” talks about his struggle with addiction. 

Unfortunately, he didn’t manage to come out of it like he wished for in the song.

15. “I Feel Like Dying” by Lil Wayne

“I Feel Like Dying” is yet another rap song that tackles the issue of drug addiction.

And since Lil Wayne has a long history of codeine abuse, it’s fair to conclude that this song is very personal.

It seems like most rap stars lead really tough personal lifes. 

16. “Death Enclaimed” by YoungBoy Never Broke Again 

Kentrell DeSean Gaulden known as YoungBoy Never Broke Again is a young American rapper.

In his song “Death Enclaimed”, he talks about his intimate fears including the fear of being shot.

The meaning of the song is actually a bit ironic since he has been charged for assault and weapons violations multiple times.

17. “Life’s A Mess” by Juice WRLD and Halsey

Juice WRLD evidently did a lot of work in the studio before he died.

“Life’s a Mess” is a promotional single off of his first posthumous studio album “Legends Never Die.”

The song talks about the pain of losing somebody you love and wanted to spend your life with.. 

18. “Colored Dreams” by Reason

Reason’s “Colored Dreams” is yet another suicidal rap song with a tragic story behind it.

It tells a story of a prisoner who commited crime to prove himself as a gangster.

Guilt eventually overwhelms him and he commits suicide in his cell. 

19. “SAD!” by XXXTENTACION

We already mentioned XXXTENTACION, a talented young rapper who was shot in 2018.

His song “SAD!” is considered one of the saddest hip hop songs of the past decade. 

It talks about dealing with severe depression and suicidal thoughts caused by problems in a relationship. 

Although many believe the song might be autobiographical, the rapper never confirmed or denied that.

20. “Hellboy” by Lil Peep 

In his rather depressing rap song released in 2016, Lil Peep talks about his fears and struggles.

To be more precise, he talks about loving someone he can’t have, and that leaves him with uneasy emotions.

21. “Sing About Me, I’m Dying Of Thirst” by Kendrick Lamar 

“Sing About Me, I’m Dying Of Thirst” is a 12-minute long emotional rap song with genuine, well-crafted lyrics.

In short, Kendrick Lamar tells a story of his friend who was a victim of gun violence.

But he does that in such an authentic and profound way.

Many agree it’s one of the best rap songs and storytelling tracks ever written.

22. “All That I Got Is You” by Ghostface Killah and Mary J Blige

“All That I Got Is You” is also one of the most emotional rap songs.

In fact, the song is Ghostface’s tribute to his mother.

He tells a story of his harsh life and all the struggles he and his family had to go through. 

23. “You Never Know” by Immortal Technique

In his song “You Never Know”, Immortal Technique talks about the platonic relationship with a girl.

The girl encouraged him to change his life for the better.

But after he tells her about his feelings, she leaves. 

It’s a rather sad rap song that probably many people find relatable. 

24. “Diva” by The Kid Laroi

The Sydney-born rapper The Kid Laroi became a true rap teen star.

He first gained recognition from his friendship with Juice Wrld while he was on tour in Australia.

He is now one of the most popular young rappers, and his song “Diva” became a hit. 

25. “6 Feet Deep” by Geto Boys

“6 Feet Deep” is one of those sad rap songs that reminds us of the struggle and harsh lives of some people.

The song is dedicated to the hip hop group’s friends who were shot. 

In the song, they promise to remember them forever. 

26. “Roses” by Benny Blanco and Juice WRLD

If you’re looking for modern sad rap songs about love, you’ll probably like our next suggestion.

“Roses” was released in 2018, and it also features singer Brendon Urie of Panic! at the Disco. 

27. “Stan” by Eminem

“Stan” is arguably one of the saddest rap songs of all time.

It’s also proof of Eminem’s songwriting skills and talent. 

Lyrically, “Stan” tells a story about an obsessed fan who struggles with mental illness and eventually commits suicide after not getting a response from Eminem. 

28. “Song Cry” by Jay-Z

When it comes to heartbreak rap songs, “Song Cry” is one of the most popular ones.

In this 2001 track, Jay-Z talks about the end of a long-term relationship and everything that happens as a result. 

It’s a song that deals with tough emotions, but we all know that he was already dating Beyonce at a time.

29. “I’ll Be Missing You” by Puff Daddy and Faith Evans, 112 

“I’ll Be Missing You” is one of the most popular sad hip hop songs.

In fact, the song became one of the best-selling singles of all time.

It’s based on a sample of the 1983 single “Every Breath You Take” by The Police.

And it tells a heartbreaking story of someone who lost his friend. 

30. “Long Gone (Save Me From This Hell)” by $Uicideboy$

This rather depressing rap song talks about the pain of losing a friend in a different way.

It’s a depiction of a hard life and the need to turn to drugs when things get rough. 

For many rappers, drugs represent the escape from their life.

31. “Tearz” by Wu-Tang Clan 

“Tearz” by Wu-Tang Clan is sad and angry at the same time.

The song tells a story of a brother who gets shot and killed on the street.

It’s supposedly not a real story about RZA’s brother, although it was always a likely outcome. 

32. “Lust” by Lil Skies 

American rapper Lil Skies released “Lust” in 2017.

The official music video shows Skies as a detective who follows a female robber.

The robber eventually drugs him and he ends up being captivated by her charm. 

33. “Changes” by 2PAC

Lyrically, “Changes” is a very powerful and somber rap song.

2PAC talks about racism, police brutality, gang violence, and other issues that don’t seem to change despite the efforts of civil rights movements.

But in essence, the song conveys a message of peace and equality, and it sounds rather hopeful and encouraging.

34. “The Message” by Dr. Dre 

Dr. Dre dedicated “The Message” to his deceased brother, Tyree.

Although its meaning is very sentimental and personal, the song sounds rather calming.

There’s probably something about the Japanese hip hop sound that can give you that impression.

35. “Acid Rain” by Chance The Rapper 

In one of his deep rap songs, Chance The Rapper tackles the themes of gun violence and police brutality.

He also laments about the absence of God and having to deal with hard feelings.

36. “Dead Homiez” by Ice Cube 

In “Dead Homiez”, Ice Cube talks about the life and death of his close friend.

His friend was shot and killed in a robbery.

Therefore, this is another song that depicts the hardship of street lifestyle.

37. “We Ball” by Meek Mill and Young Thug

Similar to the previous songs, “We Ball” is a song about pain and loss.

Meek Mill and Young Thug reminisce on the friends they’ve lost.

They refer to them as fallen soldiers.

38. “Dear Mama” by 2Pac

2Pac dedicated this popular rap song to his mother.

He talks about his childhood, sacrifices his mother made, and struggles she went through as a single parent.

All of that ultimately allowed him to succeed in the music industry, although he didn’t have an easy childhood.

39. “Broken Love” by MO3 and Kevin Gates 

Another song focused on gratitude and tough childhood is “Broken Love” by MO3 and Kevin Gates.

The lyrics also include comments on fake friends and women.

But it all ends with the verse about being tired of broken love and probably life in general.

40. “When I’m Gone” by Eminem

Eminem released “When I’m Gone” on his 2004 album “Encore.”

Essentially, the song depicts the death of his alter ego ‘Slim Shady.’

And that’s a creative way of showing how bad he feels for neglecting his family.

In a way, “When I’m Gone” is also a message of unconditional love for his daughter Hailie.

41. “Lost Ones” by J Cole

The lyrics of “Lost Ones” by J Cole are based on a dialogue between a young couple.

They’ve just discovered the girl is pregnant and they’re trying to figure out what to do.

They’re afraid that they can’t provide for the child and that they’re simply still too young. 

42. “Marvins Room” by Drake

In essence, “Marvins Room” is one of the sad rap songs about being alone.

The song is performed from the perspective of Drake who calls his girlfriend and rants about his life, loneliness, and frustrations.

The song was named after the studio it was recorded in.

43. “Last Good Sleep” by Company Flow 

“Last Good Sleep” is a 90s rap song about abusive family members.

To be more precise, it’s a story about an abusive stepdad who was abusing the son’s mother.

And it’s based on personal experiences of Company Flow’s member El-P.

In one of the interviews, El-P said that “Last Good Sleep” was his first song that had a big emotional impact on people around him.

44. “Love The Way You Lie” by Eminem and Rihanna

“Love The Way You Lie” is probably one of the most well known hip hop ballads about love and heartbreak.

It was released in 2010, and it has been played on radio stations across the world ever since.

The song sounds very powerful, but it also effectively describes the cycle of being trapped in a toxic and abusive relationship. 

45. “Keep Livin” by Jean Grae 

Although it’s lyrically quite somber, “Keep Livin” also provides a glimpse of hope.

Jean Grae talks about turning to drugs and alcohol in order to escape life, but it also reminds everyone to keep living nevertheless.

When things get rough, it’s important to keep in mind that no feeling is final.

46. “The Book Of Soul” by Ab-Soul 

“The Book Of Soul” is a soulful, melancholic rap/hip-hop tune about sadness and suffering.

It’s an honest depiction of the rapper’s complications and struggles, mostly related to his love life. 

47. “Smile To Keep From Crying” by Boosie Badazz 

The meaning behind Boosie Badazz’ song is pretty straightforward.

It’s yet another song about depression and struggling, but it’s based on a rather different story.

The rapper specifically talks about losing his three aunts within a year as well as a friend (to a gunfire). 

So lyrically, it’s a very somber tune about the tragedies of life.

48. “The Heart & The Tongue” by Chance The Rapper 

If you’re looking for newer sad rap songs, look no further. 

“The Heart & The Tongue” was released in 2021 on the rapper’s album of the same name. 

And it’s an authentic portrayal of a man’s internal conflicts.

My heart and tongue are fightin’, my mind is undecided…

49. “Perkys Calling” by Future 

In his 2016 track “Perkys Calling”, Future is talking about his addiction.

He is facing his problem and realizing that drug addiction has ruined his mind. 

And when he’s sober, he is constantly thinking about drugs – it’s a painful cycle that every addict goes through.

50. “Runaway Love” by Ludacris and Mary J Blige 

“Runaway Love” is a soulful rap song released in 2006. 

It’s about the lives of three young girls who are running away to escape their problems.

The song is memorable, sentimental and raw, so it’s not surprising that it reached #2 on the Billboard Hot 100 singles chart.

51. “Da Art Of Storytellin’ Pt 1” by Outkast

Outkast is best known for his hit “Hey Ya”, but he also wrote some good sad rap songs. 

For example, “Da Art Of Storytellin’ Pt 1” is catchy as well as emotional and compelling. 

It tells a tragic story of girls who turn to prostitution to survive. 

52. “Renee” by Lost Boyz

In short, this is a love song about a girl named Renee.

It’s captivating, catchy, and a bit gloomy.

After all, the song ends in tragedy – their relationship ends because Renee is shot to death.

53. “Millie Pulled A Pistol On Santa” by De La Soul 

In De La Soul’s 90s hip hop tune, Millie is a girl whose father works as a Santa in a shop.

It turns out that she abuses her, so she eventually pulls a pistol on him and ends his life.

It’s very somber and tragic, just like many other rap songs we mentioned today.

54. “Downtown” by August Alsina and Kidd Kidd 

“Downtown” is yet another depressing rap song about daily struggles living in the streets.

The song also deals with experiences of spending time in jail.

But despite the fact that Alsina had a difficult life, he managed to achieve a lot in his music career.

55. “Kim” by Eminem 

Eminem supposedly wrote this song about his wife Kimberly. 

In the song, he openly expresses his hateful thoughts towards her.

Although it’s considered one of his good tracks, the song shows how angry, depressed, and hostile he actually was. 

56. “Stray Bullet” by Organized Konfusion

Some critics and websites proclaimed “Stray Bullet” as one of the hip hop classics.

The song is indeed popular and impactful, and it’s around the theme of gun violence.

In fact, the hip hop duo tackles the issue by writing the lyrics from the perspective of a bullet.

57. “Suicidal” by YNW Melly and Juice WRLD  

In the remix “Suicidal”, YNW Melly and Juice WRLD express their thoughts on their problems.

And those problems are relatable to many young people as they revolve around love and breakup.

However, the song also talks about hurtful and dangerous ways of dealing with such problems.

58. “Doing It Wrong” by Drake 

Drake released “Doing It Wrong” on his studio album “Take Care” in 2011.

It’s a gentle, slow-paced song about a breakup.

Drake also used a harmonica solo from Stevie Wonder. 

Either way, it’s a good song to listen to if you’re feeling down.

59. “Loner Life” by NBA YoungBoy

Our next suggestion is “Loner Life” by previously mentioned YoungBoy Never Broke Again.

Although it’s not one of his rap songs that will make you cry, it’s definitely worth mentioning.

It’s a rather short tune, but it portrays the feeling of alienation and loneliness. 

60. “Everybody Dies In Their Nightmares” by XXXTENTACION

It’s time to wrap things up with the song by the best-selling emo rapper of all time.

In his 2017 track, XXXTENTACION raps about feeling trapped in his own mind.

The song is somber, genuine, and captivating. 

XXXTENTACION may have had a short career, but he certainly made a huge impact on the rap music scene.

Sad Rap Songs – Final Thoughts 

Most of the songs we mentioned today depict a really harsh life or tell a tragic story.

And although they’re sometimes hard to listen to, if you like rap and hip hop, they can help you get through some tough times.

Either way, we hope our article helped you find what you were looking for! 

Similar Playlists:

Best 90s Hip Hop Songs

Best 2000s Hip Hop Songs