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Top 89 Best Sad Rap Songs

Since its birth in the late-70s, with songs such as Sugarhill Gang’s “Rapper’s Delight” and Fatback Band’s “King Tim III,” Rap and Hip-Hop have become two of the biggest genres dominating the world of music. The scope of the music that can now fall under Rap and Hip-Hop is massive.

One thing most rappers have penned over the years is songs about something that saddened or still saddens them. Yes, Rap music has produced some real tearjerkers over the years. 

That’s why I decided to take a look at some of the best sad Rap songs ever recorded. Ready to get started? Okay, here, in no particular order, are my choices for the saddest rap songs out there.

Best Sad Rap Songs


Top 89 Best Sad Rap Songs

1 Dance With The Devil by Immortal Technique

Album: Revolutionary Vol. 1

Filipe Andres Coronel self-produced the first full-length Immortal Technique album, Revolutionary Vol. 1, back in 2001. Filipe sold them himself on street corners and at performances before it got picked up by Viper.

A tragic tale…

“Dance With The Devil” is considered by many as the strongest track on the album. It utilizes one of the most powerful things available to any artist – the power of a good story. In this case, the tragic tale of a youth who romanticized the lifestyle of a gangster. 

To be accepted by a gang, he agrees to take part in the assault of a woman, who ends up being his mother. Inevitably, the teen resorts to suicide to numb the pain of his shame and grief.

Quite a serious one to start a list like this. But, Dance With The Devil is an excellent example of one of the most enduring aspects of Rap music. Showing things how they are, raw and unfiltered. Not a smash hit, but a historic track from a landmark album. 

2 This Can’t Be Life by Jay-Z (feat. Beanie Sigel and Scarface)

Album: The Dynasty 

This is another hard-hitter that doesn’t hold back. The sheer amount of emotion that went into the verses is sometimes overwhelming. 

A trifecta of emotion in the verses… 

And it starts with Jay-Z. The legendary rapper is at his most vulnerable, spilling verses about his stillborn child. 

Secondly, there is Beanie Sigel, who shares his experiences of addiction and self-medication in a desperate attempt to numb the pain that sits at a much deeper level. Finding redemption and regaining a sense of self-worth come through in the verses, too, somehow.

Probably the most well-known verse is from Houston-based rapper Scarface. As he was getting ready to record his verse, he got news of a friend’s son who had passed away. At that moment, he had resolved to dedicate the verse to the memory of his friend’s son.

Talking about tragedy…

Hardcore fans remember this one for the heavy track it is. And, it will get you some nods around the room when played at a party. 

3 U by Kendrick Lamar 

Album: To Pimp A Butterfly 

Lamar’s reputation as one of the heavyweight rappers was already beginning to solidify when he got round to recording To Pimp A Butterfly. Much of the influence came from Kendrick’s visit to South Africa, where he saw several historical sites, including Nelson Mandela’s Jail Cell on Robben Island. 

“U” is considered one of the most vulnerable songs in Kendrick’s entire catalog. And there are grounds for this when you look at the subject matter. As well as that, Lamar said that it was one of the hardest tracks to work on because of the issues it dealt with. 

Disappointment in oneself and others, your defects, and deepest insecurities are never easy subjects. However, Lamar spits out verse after razor-sharp verse that bears repeat-listening. This might not be one of the big singles from his landmark third album, but it sure is one of the heaviest. 

4 Smile To Keep From Crying by Boosie Badazz

Album: In My Feelings (Goin’ Thru It)

Boosie has never had a problem imparting emotion into his performances and recordings. This is largely thanks to that wonderful Southern drawl in his voice. It allows him to seamlessly add weight and sincerity to anything he might be singing about, even if it happens to be a ridiculous subject.

Although, on this track, Boosie chose anything but a light or ridiculous subject. This is reflected in the tone and style of the backtrack. No doubt some expert hands were tweaking knobs and faders on this one. 

Dealing with losses…

With his distinctive blend of vulnerability and pure conviction, Boosie raps about the last year he had. Losing three aunts, being forgotten by a girl he was close to when locked up, and finally, losing a close friend to gun violence. 

All things anyone would find tough dealing with are expressed here to a very real degree. As a result, it is one of the best sad Rap songs I have ever heard.

5 Keisha’s Song by Kendrick Lamar

Album: Section.80

As mentioned, Lamar’s reputation as one of the heavyweights is unquestionable. But, when Section.80 was being made, Lamar had only made a few mixtapes. 

This album would soon bring his name to the world in a big way. Among the themes explored are the 1980s crack epidemic, racism, and the medication tolerance of Generation Y.

A darker side of society…

This track deals with the harsh lives some people end up leading because they are doomed products of a broken system we call modern society. “Keisha” refers to a real person whom Kendrick considered a childhood friend. 

The song lays out how she was molested and abused as a child. This would eventually lead to her getting addicted to drugs and turning to prostitution to stay alive. 

The story doesn’t culminate in some hopeful flicker, though; true stories often do. Keisha ended up getting stabbed to death at the age of seventeen. If you want a depressing Rap song, this is right up there.

6 Acid Rain by Chance The Rapper

Album: Acid Rap

Acid Rap is far removed from the music that Chance The Rapper is making these days. But, you can hear the voice that would grow into what it’s now become on the album. 

The mixtape made it onto the Billboard Top R&B/Hip-Hop Albums chart purely by downloads, debuting at #63. After achieving over one million downloads on Datpiff, Acid Rap was certified platinum. 

Inherent darkness lingers in the album… 

There is a deep sense of despair conveyed by the strained-sounding performance and the simple repetition of certain lines. The trauma of having to watch his friend die still haunts Chance. 

He lays it bare on this track with bold unabashed honesty. And, you get the sense of having witnessed something a bit scary with lines like, “I see it always he still be screaming/I see his demons in empty hallways.”  

Seeing where Chance is now, it’s good to look back at this difficult time through the lens of music and know that he’s doing much better now. That being said, this remains one of his best tracks, although it’s one of the darkest Rap songs as well. 

7 Brenda’s Got A Baby by 2Pac

Album: 2Pacalypse Now 

2Pac’s debut was full of hard-hitting criticism. Much of his commentary on society was conveyed using the plight of impoverished people as his vessel. The talent for lyricism and truthful criticism was already shining bright on the legendary rapper’s first album. 

“Brenda’s Got A Baby” was inspired by a news article that 2Pac read during the filming of the 1992 crime film “Juice.” The article told the story of a young girl who had gotten pregnant by her cousin and had decided to throw the baby into a trash compactor. 

Inspiration from horror…

This track became 2Pac’s symbol for teen mothers across the United States and even the world. Using her story, he shared his thought on the unfairness of life, the unjust treatment which we find in a so-called “just system,” as well as the government. 

“Brenda’s Got A Baby” peaked at #7 on the US Billboard Hot Rap Songs chart and #23 on the US Hot R&B/Hip-Hop Songs chart. More importantly, it’s become a seminal song in the catalog of one of the most influential rappers of all time. And is easily one of the best sad Rap songs as well.

8 Jocelyn Flores by XXX Tentacion

Album: 17

Artists will often impart personal experiences, thoughts, and emotions through their work. Having the courage to share personal things (especially if they are liable to reflect negatively on you) is not something easily done. 

XXX Tentacion chose to do just this when he wrote and released “Jocelyn Flores.” His reasons for doing so are his own. But just having the guts to rap about something this tragic and close to you and then putting it out there, already deserves respect. 

Mystery and murder…

Sixteen-year-old Jocelyn Flores had infatuated XXX via her Twitter photographs. He ended up inviting her to do modeling for his Revenge line of clothing. The arrangement came to an abrupt end due to an incident at his house. 

That resulted in the rapper asking Jocelyn, as well as another girl who had been living with him, to leave. The 16-year-old proceeded to check herself into a hotel and was found dead the next morning. 

“Jocelyn Flores” debuted at #31 on the US Billboard Hot 100. After XXX Tentacion’s murder in June of 2018, the track eventually peaked at #19. It entered the UK Singles chart at #56. And it also made it to #14 on the UK R&B Chart and peaked at #2 on UK Independent Chart. 

9 Sing About Me, I’m Dying of Thirst by Kendrick Lamar

Album: Good Kid: M.A.A.D City

I’m quite sure an army of Lamar fans would have stalked me for weeks had I not included this track on the list. It’s become such a titanic part of Rap and Hip-Hop lore that it’s taken on an almost holy aura. 

A Hip-Hop Epic

Not just a great sad rap song but one of the greatest Hip-Hop compositions of the century. If ever there was such a thing as a Hip-Hop epic, this would be it. 

The track clocks in at just over twelve minutes, during which two distinct narratives unfold. The first one is named “Sing About Me” and is about seven minutes long. Then, there is a short skit, and the second part, “I’m Dying of Thirst,” begins and lasts for just under three minutes. 

Lamar makes use of characters from previous albums and other songs on Good Kid: M.A.A.D City to tell his two stories. As far as lyricism and rhythm, this track solidifies Lamar’s status as an absolute master of his craft. 

The first seven minutes… 

You get taken into the world of “Dave,” who is eventually lost to gun violence and leaves behind a brother consumed and poisoned by revenge. The last two minutes and fifty seconds lays bare the tale of a young girl who, like so many others, has turned to prostitution to make a living. 

If someone were to ask me for one song to introduce them to Kendrick Lamar, it would probably be this track. One of his absolute masterpieces and easily one of the most memorable sad Rap songs ever recorded.

10 We Ball by Meek Mill (feat. Young Thug)

Album: Wins & Losses

“Explicit Content” has never been an issue when it comes to Rap and Hip-Hop. It is the very culture that gave us the saying, “Tell It Like It Is.” Writing what you know is always a surefire way to guarantee sincerity in the lyrics as well as the performance. 

Meek Mill has become one of the most recognizable voices in Rap music in recent years. On this track, he lays bare personal issues on a different level when compared to his other material. Together with Young Thug, Meek relays things he knows, and not everything is nice.

Dealing with the pain…

Rap and Hip-Hop songs often revolve around violence with aggressive energy. However, “We Ball” relays a sense of despair and hopelessness at the amount of pain one must sometimes endure. The best summary of this may be the few lines near the end of Young Thug’s verse:

“You can’t question God/yeah yeah/Or any of these challenges/Sipping on this Actavis/I swear I gotta manage it.”

Tell it like it is, indeed.

11 Beautiful by Eminem

Album: Relapse

When Eminem went to rehab in 2005, he penned the first two verses of this tune. He wasn’t able to add that third verse until he got clean a few years later and began working on Relapse, released in 2009. 

The track features a sample from the song “Reaching Out” by the British band Rock Therapy. However, the version sampled for “Beautiful” is from a Queen+Paul Rodgers live performance. Eminem was probably aware that his song “Lose Yourself” was used as House music during that concert.

The track falls in with the theme of introspection that dominates the entire Relapse album. But, it does have a softer tone when compared to the other tracks. 

The music video adds another dimension to the lyrics… 

The video starts with a caption stating that in 1950 Detroit was the greatest manufacturing city in the world. It then shows Eminem walking through Michigan Central Station, the former Packard plant, and Tiger Stadium. All of which are now abandoned and, in one case, demolished. 

“Beautiful” peaked at #12 on the UK Singles chart. It also made it to #17 on the US Billboard Hot 100 and was nominated for two Grammy’s – Best Rap Solo Performance and International Video of The Year. 

12 Changes by 2Pac (feat. Talent)

Album: Greatest Hits

Some songs are like a barrel of wine. Slowly aged and refined to perfection. Other songs, like this one, are small pieces stitched together to make a whole blanket of music. 

The track and samples can be seen as an interpretation of Bruce Hornsby and The Range’s hit, “The Way It Is.” The original song was influenced by Black Sabbath’s song “Changes.” 2Pac also borrows lines from some of his other songs, including “I Wonder If Heaven Got A Ghetto.” 

Truth in metaphor…

Once more, we have 2Pac using the power of metaphor as a vessel for his messages. This one centered around American drug policy, treatment of folks of color, and the vicious cycles of poverty and violence our society produces. 

The track is widely considered to be one of the greatest 2Pac songs ever recorded. It earned a Grammy nomination for Best Rap Solo Performance and remains the only posthumous song ever to be nominated in the category. 

Additionally, it was an international hit, making it onto the charts in various countries. Eventually, “Changes” was certified platinum in the UK and Sweden. Although it wasn’t a Rap song about sadness, it was steeped in the sorrow many are trying to change.

13 Stan by Eminem

Album: The Marshall Mathers LP

The relationship between successful artists and their fans has always been strange. Some folks find so much meaning in the lyrics of a song that they become disillusioned with their reality. 

Eminem is one artist who has inspired some of the most fanatic fans in history. And with “Stan,” he chose to relate this disillusionment by becoming his own obsessed fan named Stanley. 

In the music video… 

Stanley lives with his pregnant girlfriend, played by British singer Dido, whose song “Thank You” is sampled in the song. Stan is obsessed with Eminem and constantly writes him letters conveying his devotion to Em’s music. 

As the song progresses, Stanley becomes convinced that he has some kind of personal connection with the rapper. He becomes sadder and angrier by Ems’s indifference toward his story. Eventually, Stan ends up killing himself and his pregnant girlfriend in a car crash. 

Since the release of the song… 

The term “Stan” has become a slang term for overzealous, maniacal, overly obsessed, entitled fans. Furthermore, it has even been added to the Oxford English dictionary. 

Stan has become of Slim’s signature songs and one of the biggest rap songs in history. It was #1 in Australia, Austrian, Finland, Denmark, Germany, Iceland, Ireland, Italy, Romania, Scotland, and the UK. 

It has been certified quadruple-platinum in the US, triple-platinum in the UK, and double-platinum in Australia. As a result, it’s one of the best sad Rap songs you will ever hear.

14 The Message by Dr. Dre (feat. Mary J. Blige and Rell)

Album: 2001 

Dr. Dre is the man who brought Gangster Rap to the masses. His distinctive style, combined with controversial lyrics, made him a force to be reckoned with. And, when it comes to respect, he commands everyones. 

Yet, in this song, we have the maestro reflecting on his legacy and his losses. Not with boastful pride, but with questions and a message to the Almighty. Within the first verse, Dre wants to know why God would bother having wonderful people come into the world only to take them prematurely.

In the hands of the Almighty…

The flawless way he weaves complex messages in the first four lines of the track attests to the honed skill of a true master. Opposing the lyrics is how they are delivered. The performance is that of a mere man. One who, even after years of learning, still wonders why certain things are part of the Divine Plan.

We even see Dre tipping the hat to those who helped make him, a legend who still has his humility. For me, this is one of Dre’s best tracks because of the honesty and power of the content. 

15 Colored Dreams by Reason

Album: There You Have It

If we classified music in the same genres we classify films and books; Rap would have a large part of its catalog dedicated to Tragedy. 

Rap music often deals with, or is inspired by, real events that the artists witness or live through. And, the characters and stories don’t see any kind of “happy ending.” Life isn’t like film or literature. 

This track is told from the perspective of a convicted killer serving out his sentence. At first, he only contemplates things around him and his immediate circle, most notably his mother. Oddly enough, a reference to Queen’s monster hit, “Bohemian Rhapsody,” opens the tune.

As the first verse begins… 

We see our character reflecting only on what has happened and what lies ahead in his future. However, time brings a broader perspective and the dawning of new thoughts, redemption, and compassion for those whose lives he has irrevocably changed.

Tragically, redemption does not find our character, and he ends up looking for a way out. A means of numbing the pain he lives with due to the choices he made to be accepted by a gang. He ends up realizing that the aspirations he was chasing were empty, to begin with, and he renounces them.

Despite this revelation, the loss of friends and family weighs too heavy, and he ends up taking the only way out that he sees left. This “way out” poetically ends by cutting the last chorus short.

16 Suicidal Thoughts by Notorious B.I.G

Album: Ready To Die

Notorious has become legendary for many reasons. But mostly, it was his skill as a rapper and his vision as an artist. Something he was known for doing from the start was storytelling. With the album, Ready To Die, he told what has become one of the biggest Rap and Hip-Hop stories in history

Ready to Die is one of the seminal concept albums of the century. Even the album cover depicting a baby photo of Notorious but edited with a giant afro already lays it out. Here is a life story told by the man who lived it. This epic tale finally culminates in its final track.

As with many Notorious B.I.G songs… 

Explicit lyrics tell a story that has a harsh realness to it. Sometimes, it makes the listener uncomfortable. But, it confronts you with realities that cannot, nor should not, be ignored. The narrator’s mood only worsens as the track peddles on. Friends trying to motivate a change in his thought pattern does little to stop the inevitable downwards spiral.

Ready To Die is one of the most successful and critically-acclaimed Rap/Hip-Hop albums of all time. One of the things most praised by critics and fans alike is the storytelling. It was certified double-platinum one month after its release. 

Since then… 

It has only built momentum. Eventually, it was certified six-times platinum in 2018. Rolling Stone ranked Ready To Die as #1 on their 200 Greatest Hip-Hop albums of all time. And, of course, one of the best sad Rap songs of all time.

17 8 Million Stories by A Tribe Called Quest 

Album: Midnight Marauders 

Sometimes, it’s the little things that get you down. They don’t hit you with full force like the big punches. No, they build up and finally spill over into a complete mess. 

This melancholy number from A Tribe Called Quest is perhaps not the most tragic Hip Hop song ever. But, there is a shade of sadness there, a more common kind of feeling that makes it so much more relatable. 

Everyday things that happen to everyone everywhere. They can get you down just like anything. It’s nice to have a track like this to go to when that happens.

18 Da Art of Storytellin’ (Pt. 1) by Outkast

Album: Aquemini

This heartbreaker was released as the final single for Outkast’s third album. There are two dimensions to its sadness, although one of them has a silver lining.

First, we have the story itself. Like many hip-hop tracks, there is brutal explicitness to the picture that the artist paints of modern American society. Poor Susie Screw’s life seems depressing enough. But, we are exposed to a more disturbing view of Sasha Trumper’s life as well.

I did say there were two dimensions to the sadness. The story is the first, and the second is that the track did not perform well chart-wise. The silver lining, though, is that it has since become a fan favorite. And is regarded as one of the best Outkast songs ever by critics and listeners alike.

19 Slippin’ by DMX 

Album: Flesh of My Flesh, Blood of My Blood

“Slippin’” is nothing short of a lyrical bio delivered to perfection over a well-produced track. DMX’s story shares similarities with thousands, if not millions more. That’s why it found resonance among so many. 

The picture painted of his adolescence speak of many things that shouldn’t have happened but did. And many things that should have happened, but didn’t.

This track samples a Grover Washington Jr. song, “Moonstreams.” It peaked at #30 on the UK Singles chart and #60 in the US. It has since been certified platinum in the United States. 

20 I’ll Be Missing You by Puff Daddy (feat. Faith Evans and 112)

Album: No Way Out

Understandably, one of the saddest Hip Hop songs ever written is a tribute to one of the greatest rappers in history. The passing of Notorious B.I.G is impossible to quantify in mere words. Yet, what Puffy ended up producing and performing, transcended music and words. 

Initially, much controversy surrounded the song due to the use of The Police’s massive hit “Every Breath You Take.” It resulted in Sting receiving all the royalties for the tune. That being said, it stands as a tribute to B.I.G, and Sting even performed the song with Puff Daddy once.

And so the dust settled…

Commercially, it was and still is a huge hit. Even standing up to the song that it samples. “I’ll Be Missing You” topped the charts in fifteen countries, including Austria, Australia, Denmark, Belgium, Canada, Germany, Iceland, Ireland, and the Netherlands. 

It spent fifteen weeks at the top of the US Billboard Hot 100 and won the Grammy for Best Rap Performance by a Duo or Group. It is one of the best-selling singles of all time

21 One Life by The Last Emperor

Album: Music, Magic, Myth 

When people talk about Rap music getting “too real,” songs like “One Life” are liable to come up in the conversation. It is said that The Last Emperor had undergone chemotherapy just before he recorded the verse for this track. 

Whether that’s true or not doesn’t matter. What matters is the openness with which he addresses his battle with cancer. And the strength of his resolve to fight as hard as he can.

I’m quite happy to say that the fight isn’t over, and The Emperor shows no sign of slowing down.


23 Long Gone (Save Me From This Hell) by $uicideboy$

24 Love Scars by Trippie Redd

25 Tearz by Wu-Tang Clan

26 Book of Soul by Ab Soul

27 Jonylah Forever by Lupe Fiasco

28 Millie Pulled A Pistol on Santa by De La Soul

29 Retrospect for Life by Common f/ Lauryn Hill

30 Dance by Nas

31 Mockingbird by Eminem

32 Difficult by Eminem

33 Dear Mama by 2Pac

34 Earl Sweatshirt by Solace

35 Earl Sweatshirt by Red Water

36 Earl Sweatshirt by Faucet

37 Madonna (And Other Mothers In The Hood) by Lupe Fiasco

38 APIDTA by Jay Electronica

39 Lost Ones by J Cole

40 Cant be life by Jay Z

41 Keep Livin by Jean Grae

42 Yesterday by Atmosphere

43 Virgo by Atmosphere

44 Like the rest of us by Atmosphere

45 Guarantees by Atmosphere

46 Became by Atmosphere

47 Flicker by Atmosphere

48 For Whom the bell tolls by J.Cole

49 Happy Birthday by Flipsyde

50 My Life by The Game

51 Like Toy Soldiers by Eminem

52 Runaway Love by Ludacris

53 Thank You by Xzibit

54 Good Die Young by D12

55 Proof by Kurt Kobain

56 Love the Way You Lie by Eminem

57 You Never Know by Immortal Technique

58 Breathin by T-Rock

59 My Block by 2Pac

60 I Seen a Man Die by Scarface

61 Renee by Lost Boyz

62 Dead Homiez by Ice Cube

63 Stray Bullet by Organized Konfusion

64 Ballad of Worms by Cage

65 Tha Crossroads by Bone Thugs-n-Harmony

66 D Rugs by Cam’ron

67 Uncommon Valor: A Vietnam Story by Jedi Mind Tricks f/ R.A. the Rugged Man

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

70 Summertime by Vince Staples

71 Perkys Calling by Future

72 I Feel Like Dying by Lil Wayne

73 Last Good Sleep by Company Flow

74 DNA by Earl Sweatshirt f/ Na’kel

75 Callin My Phone by Lil Tjay, 6LACK

76 Finesse Out The Gang Way by Lil Durk, Lil Baby

77 Clown World by Tom Macdonald

78 Fools (can’t help falling in love) by Foster, Sody, Sarcastic Sounds

79 Toxic Punk by Young Boy Never Broke Again

80 Fake Woke by Tom MacDonalds

81 Street Runner by Rod Wave

82 Death Enclaimed by Youngboy Never Broke Again

83 Broken Love by Mo3 Kevin Gates

84 I Ain’t Perfect by Mozzy, Blxst

85 P2 by Lil Uzi Vert

86 Suicidal by YNW Melly, Juice WRLD

87 Don’t Need Time by HOTBOII, Lil Baby

88 Diva by The Kid Laroi, Lil Tecca

89 The Voice by Lil Durk

Looking for Awesome Hip-Hop Songs?

We can help with that. Take a look at our detailed articles on the Best Kanye West Songs of All Time, the Best Drake Songs of All Time, the Best Lil Wayne Songs of All Time, the Best Ja Rule Songs Of All Time and the Best Kid Cudi Songs for more great song selections.

Of course, you need to jam to those tunes. So, check out our in-depth reviews of the Best Bass Earbuds, the Best Sound Quality Earbuds, the Best iPhone Earbuds, the Best Headphones for Music, and the Best JBL Wireless Headphones you can buy in 2023.

Best Sad Rap Songs – Final Thoughts

Whether trying to send a message on behalf of millions who have no voice or expressing pain and regret, Rap music can and has provided a vessel for that since its birth. From the hard-hitting and intelligent criticism of 2Pac to the simple relation of a battle against a deadly disease by The last Emperor, Rap music can help express sadness in all its forms. 

No doubt, other super sad Rap songs could have a place on this list. So, what are some of your honorable mentions? Tell us in the comments below.

Until next time, happy listening.

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About Corey Hoffman

Corey is a multi-instrumentalist who has played in numerous bands over the years, some good, some not so good. He has also written countless songs and recorded five albums in professional studios across America. Today he is a hobby musician but still loves the guitar after over 15 years of playing.

He considers his writing as a way to share what he has learned over the decades with younger generations ad always can't wait to get his hands on the latest gear.

He lives just outside New York with his wife Barbara and their two German Shepherds, Ziggy and Iggy.

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