The 35 Most Depressing Rap Songs

Throughout the decades, hip-hop has produced plenty of songs about emotional darkness and depression. For a genre that grew out of urban plight, it’s natural at least some of the lyrics reflect those misfortunes and their effects on the psyche. From Jay Z to J. Cole, here are 35 of the most depressing rap songs.

depressing rap songs outkast

Image via Getty/Jeff Kravitz

depressing rap songs outkast

Hip-hop has been cranking out living-it-up bangers for decades, but the average historian is (or should be) aware that dark thoughts aren’t a foreign concept for the genre. After all, Grandmaster Flash & the Furious Five’s 1982 classic “The Message” wasn’t exactly a joyful number. The bleakness feels natural for a culture that grew out of urban plight and the trauma of impoverished people of color; it makes sense that at least some of the lyrics reflect those misfortunes and their lasting effects on the psyche.

Still, treating that pain as a mental health issue has been a recent development. Jay Z—who once rapped about being hard in the pursuit of hard cash in 1996’s Reasonable Doubt—became one of the main voices of that shift during the 4:44 campaign. “Three of your brothers are dead and your mother used to beat you,” he said in one of his Footnotes episodes. “You need help. Someone needs to talk you through why you’re feeling these feelings.”

Many other rappers have embraced vulnerability in recent years, including Freddie Gibbs, Kanye West, and J. Cole—even when male emotional introspection and mental health weren’t part of the dominant narrative. Company Flow’s classic Funcrusher Plus notably took a break from dense rhyming for El-P to hauntingly remember his abusive stepfather. Kendrick Lamar’s “u” explicitly reveals his pain behind closed doors—being the greatest rapper in the world can only heal so much (Lamar on the song: “That was one of the hardest songs I had to write....That shit is depressing as a motherfucker. But it helps, though. It helps”). Then there’s the personal dispatches from the hedonistic realms of Future and Lil Wayne.

Like anyone else, the rappers and hip-hop artists of our day are dealing with their own shit; what better way to express themselves then to hop on the mic and vent about it? This is our round-up of the most depressing rap songs.


35. Jay Z f/ Beanie Sigel and Scarface “This Can’t Be Life” (2000)

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One of Jay Z’s most unguarded moments features him talking about his stillborn child, and his hitter Beanie Sigel speaking on self-medicating his inner pain. But of course, the legacy around the song mainly comes from the backstory behind Scarface’s verse. The Houston legend found out his friend’s son died as he was in the studio about to record his verse. So he dedicates it to him: “I could've rapped about my hard times on this song / But heaven knows I woulda been wrong.” The reason his performance is so revered is because of its deeply affecting mix of clarity and heartbreak.

34. Boosie Badazz “Smile to Keep From Crying” (2016)

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Boosie Badazz’s distinctly southern drawl comes with a bluesy quality, so he rarely has trouble selling the emotion at the core of his songs. A key recent example is the mournful “Smile to Keep From Crying.” The title is a cliche, but when you think about losing three aunts in a year, being bitter about a girl who wouldn’t write him in jail, and losing a friend to gun violence—along with the conviction with which he raps—it’s a valid expression of pain.

33. Chance the Rapper “Acid Rain” (2013)

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Chance’s music has turned nearly full tilt toward positivity and Christian overtones in recent years. Though his breakthrough Acid Rap has some of that spirituality, it’s mixed in with drug tales and some of his catalog’s darkest moments. “Acid Rain” surveils a sense of hopelessness around him and the lingering trauma of watching his friend Rodney Kyles Jr. die. “I seen it happen, I seen it happen,” he says, with pained repetition. “I see it always he still be screaming / I see his demons in empty hallways.” “Acid Rain” makes it clear that Chance’s faith has been tested—which is perhaps why it’s so strong.

32. Meek Mill f/ Young Thug “We Ball” (2017)

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In which Meek Mill—one of the electrifying rappers of the decade—turns down the volume a bit to reveal his scars alongside Young Thug. “We Ball” is a reminder that Meek Mill’s tale is also a story of loss. Dex Osama, Lil Snupe, and Lor Scoota—who Meek Mill shouts out in the song’s opening seconds—all died from gun violence. Snupe was just 18. Meek and Thugger both escaped coming up within proximity of that sort of violence. “We Ball” explains that very haunted sense of freedom. “You can't question God, yeah yeah, or any of these challenges / Sipping on this Actavis, I swear I gotta manage it,” Thugger weeps near the end of his verse, summarizing the song’s pain.

31. Earl Sweatshirt f/ Na’kel “DNA” (2015)

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Na’kel’s main focus isn’t rapping, yet he walked away with one of his highlights with this contribution to I Don’t Like Shit, I Don’t Go Outside, a project from prodigious rapper Earl Sweatshirt. As Earl told NPR, Na’kel wrote his verse right after finding out a close friend died. He didn’t need that much technical ability to express a just-opened wound. The result is a wrenching set of bars that mixes grief-in-process with sweetness. “I'm going to London on the first, I'm bringin’ you somethin’ back,” Na’kel says, yelping to the heavens.

30. Company Flow “Last Good Sleep” (1997)

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After spending the album unspooling tangly rhymes over septic beats, Company Flow start to bring Funcrusher Plus to a close with an El-P cut about his experiences with domestic abuse. It’s a dark switch-up even for an album this gritty, but El-P compels with the detailed perspective of a child bearing witness to an abusive stepfather. It’s the lingering effects with which he ends the song that sting the most: “I see him every night / And cover my ears in tears as he beats his fucking wife.” Even El-P was taken aback by how affecting that track was. "I didn't think anyone wanted to hear that shit—like, 'Boohoo,'" El-P told Rolling Stone. "But after that song, people started coming to me with tears in their eyes."

29. Lil Wayne “I Feel Like Dying” (2007)

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Even Lil Wayne had to open up about his personal struggles during his commercial peak at the end of last decade. In “I Feel Like Dying,” Wayne moves away from his fluid flow for a delivery that feels impressionistic and bluesy. He paints the verses with fantastical imagery (“I can play basketball with the moon / I got the whole world at my feet”), but the songs hook makes it very clear this is a dark sort of escapism: “Only once the drugs are done / Do I feel like dying.”

28. Future “Perkys Calling” (2016)

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Future’s music usually traffics in 0 to 100 hedonism, but he’s been fairly open about the lifestyle’s costs. “Perkys Calling” is one of his most straightforward, transparent revelations about addiction, an eyes-tightly-shut expression of pain that makes itself explicit from the hook. Of course, Super Future flexes (“Started rockin' Balmains like they Levis”), but here, it only draws a deep unhappiness into focus. “I need better thoughts, I need better vibes,” he says right after mentioning his success.

27. Vince Staples “Summertime” (2015)

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There’s a numbness that sometimes creeps into Vince Staples’ verses when he’s rhyming about black plight. “Summertime” is one of the few times he reveals the heartbreak behind that ice front. Arriving at the midway point of his debut Summertime ’06, Staples switches to a croaky singsong while looking at a romance that wasn’t meant to live. Staples’ philosophy runs adjacent to “it is what it is,” but that doesn’t stop him from wanting more. He ends the song with a futile plea: “Pick up the phone, don't leave me alone in this cruel, cruel world.”

26. Kendrick Lamar “u” (2015)

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“Alright” can bring joy in just about any setting, but its light shines brighter within To Pimp a Butterfly’s sequence, because it follows right after one of Kendrick Lamar’s darkest moments. The anguished “u” finds Lamar venting himself hoarse as he struggles with his insecurities and mourns the lost of his close friend. The latter part—rapped over haunted piano plunks and weepy saxophones—is particularly affecting, because the level of detail shows that Lamar is truly spilling a piece of himself: “You even FaceTimed instead of a hospital visit / Guess you thought he would recover well / Third surgery, they couldn't stop the bleeding for real.” While the praise around To Pimp a Butterfly felt borderline messianic, “u” is a reminder that there’s a human struggle at the center of it all.

25. Immortal Technique "Dance With The Devil" (2001)

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Album: Revolutionary Vol. 1

Producer: 44 Caliber

Label: Viper

Through a sick and twisted turn of events, a young man infatuated with the street lifestyle winds up beating and gangraping his own mother. This cautionary tale is the poster child for depressing rap songs.

24. Pete Rock & CL Smooth "They Reminisce Over You (T.R.O.Y.)" (1992)

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Album: Mecca and the Soul Brother

Producer: Pete Rock

Label: Elektra

"T.R.O.Y." will always stand above the pack because of Pete Rock's legendary production, but there's also a sad story at its core. The record was inspired by the death of the duo's friend Troy Dixon, who most know as "Trouble" T. Roy of Heavy D & the Boyz. CL's rhymes do his memory justice, but one can't escape the song's feeling of loss that stems from his absence.

23. Jedi Mind Tricks f/ R.A. the Rugged Man "Uncommon Valor: A Vietnam Story" (2006)

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Album: Servants in Heaven, Kings in Hell

Producer: Stoupe

Label: Babygrande

Tragic historical events are no less unfortunate because they're obscured in the past. Jedi Mind Tricks and R.A. The Rugged Man realized this and used that sentiment to craft a story about the Vietnam War. The record successfully sheds some light on a dark period in American history, and probably even served to educate a good amount of folks who were unfamiliar with the conflict.

22. Cam'ron "D Rugs" (1998)

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Album: Confessions of Fire

Producer: Darrell "Digga" Branch & Lance "Un" Rivera

Label: Untertainment, Epic

Killa Cam is mostly celebrated for his flamboyance and braggadocio, but he's still capable of delving deeper. On "D Rugs" he takes a refreshingly honest look at the effects drugs have on him, his community, and his own mother. It's a fateful ending for all parties involved.

21. Bone Thugs-n-Harmony "Tha Crossroads" (1996)

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Album: E. 1999 Eternal

Producer: DJ U-Neek

Label: Ruthless

This record's massive popularity keeps most from even looking at it in an emotional light anymore, but when removed from the context of its pop success, the fact remains: This is one chilling record. "Why'd they kill my dog?" still has no answer, and Uncle Charles is still missed.

20. Cage "Ballad of Worms" (2002)

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Album: Eastern Conference All Stars III

Producer: Cage, Camu Tao

Label: Eastern Conference

There are seemingly endless message board debates over whether this song's meaning is literal, or a metaphor for hip-hop, or at least a girl who's addicted to drugs. Either way, all of the above scenarios are depressing. There's a swift current of despair and hopelessness running all throughout the record, and that doesn't change, even when the perceived meaning does.

19. Dr. Dre f/ Mary J. Blige & Rell "The Message" (1999)

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Album: 2001

Producer: Lord Finesse

Label: Aftermath

Dr. Dre speaks about personal loss with an admirable level of selflessness. He focuses on the qualities of his lost friends, and his faults in his relationships with them. Even after his pivotal role in bringing "gangster" to the mainstream, Dre questions if he is a gangster and admits to crying over the deaths addressed in the song. Keeping it that real might just solidify his G.

18. Organized Konfusion "Stray Bullet" (1994)

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Album: Stress: The Extinction Agenda

Producer: Organized Konfusion

Label: Hollywood BASIC

Stray bullet deaths don't get nearly enough attention, but there's a conscious attempt to bring some light to the tragic incidents here. The graphic detail in which the deaths of children are described are enough to make you reconsider your stance on the Second Amendment.

17. Nas "Dance" (2002)

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Album: God's Son

Producer: Chucky Thompson for The Hitmen

Label: Columbia

Forgive Nasir's singing on this record. We won't even call it ill-advised. If one feels compelled to sing about their wish to have one last dance with their mother, they by all means should, no matter their level of traditional vocal talent. In fact, it's the vulnerability in Nas' voice that makes this record even more touching. Losing a mother is one of life's toughest curveballs, and Nas makes no attempt to mask that, to great effect.

16. Ice Cube "Dead Homiez" (1990)

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Album: Kill At Will

Producer: Chilly Chill

Label: Priority

The fact that death doesn't even sound like it phases Ice Cube is what makes this record so depressing. As the lyric goes, "The city is so fucking messed up," but instead of countering this, there's pure desensitization. It seems like conditions will never improve, and unfortunately, the people plagued by the violence in the urban communities Ice Cube is rapping about here have accepted it.

15. Lost Boyz "Renee" (1996)

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Album: Legal Drug Money

Producer: Mr. Sexxx

Label: Uptown

"Renee" isn't an excessively sad song, but it is a constant reminder that life is sacred, and anyone can go at any time. When news of her demise comes, you can sense the panic begin to occupy the record. The ambiguous nature of her gun-related death makes the narrative all the more haunting.

14. A Tribe Called Quest "8 Million Stories" (1993)

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Album: Midnight Marauders

Producer: Skeff Anselm

Label: Jive, BMG

Sometimes depression is just about the simple losses—not death, disease, or drug addiction—and "8 Million Stories" nails that frustration. Phife Dawg weaves a narrative that involves the store not having what he wants, his sports team not performing up to par, his car getting broken into, and other daily mishaps. Its relatable, and ultimately, just as relevant of a plight.

13. OutKast "Da Art of Storytellin' (Part 1)" (1998)

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Album: Aquemini

Producer: Mr. DJ

Label: LaFace, Arista

The fact that Susie Screw gives Big Boi head in a parking lot for a CD and a poster is depressing enough, but it's the story of her "partner" Sasha Thumper that's especially unsettling. When Andre 3000 poses the question, "What you wanna be?", her response is, "Alive." Fictional or not, Sasha's circumstances are already tough to swallow, but the kicker about how she was "found in the back of a school with a needle in her arm, baby two months due" really traps in the misery.

12. DMX "Slippin" (1998)

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Album: Flesh of My Flesh, Blood of My Blood

Producer: DJ SHOK

Label: Ruff Ryders, Def Jam

DMX has found himself in the midst of legal drama for most of his adult life, and "Slippin'" offers an unfortunate insight into what may the root cause of that behavior. X explains his youthful exploits in harrowing detail over a sufficiently moody Grover Washington Jr. sample, giving some context to his oft-publicized problems with the law. It's a sad story that makes you reconsider, and possibly stop judging, the rapper's complicated life path.

11. Jay-Z "Song Cry" (2001)

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Album: The Blueprint

Producer: Just Blaze

Label: Roc-A-Fella, Def Jam

On most of the Jay-Z songs that deal with heavy personal subject matter, you get the sense that he's achieved some level of closure. Talk of a stillborn child on "This Can't Be Life" is followed by, "Still I gotta move on." The anger directed towards his absentee father on "Where Have You Been" is eventually met with the smug charms of success by the end of that verse. But none of that exists on "Song Cry." Jay-Z broke a young woman's heart, had his broken in return, and has to live with it forever. There's not even a sorta happy ending here.

10. Puff Daddy f/ Faith Evans & 112 "I'll Be Missing You" (1997)

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Album: No Way Out

Producer: Sean Combs, Steven Jordan

Label: Bad Boy

This song was a pop hit, so sometimes we get caught in the melody and forget its original purpose and intent. Sean Combs lost a best friend and creative partner. Faith Evans lost a husband and father to her children. Listening to them navigate that pain on this record will always be difficult on some level.

9. The Last Emperor f/ Poetic "One Life" (2003)

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Album: Music, Magic, Myth

Producer: Set Free

Label: Raptivism

It's not often that rap gets this real, and personal. Rumored to have undergone chemotherapy treatment directly before recording his verse, Poetic openly addresses his fight with cancer on the record. He tragically lost that fight soon after, but "One Life" will always stand as a testament to the bravery with which he endured the struggle.

8. Common f/ Lauryn Hill "Retrospect for Life" (1997)

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Album: One Day It'll All Make Sense

Producer: James Poyser, No I.D.

Label: Relativity

Rarely is abortion discussed in hip-hop, and especially not to the extent that Common does on this single. He appears to have mostly come to terms with the decision, but a somber tone of regret lingers. It makes for a sad story, but knowing that the unborn child's nonexistent life may be better than the circumstances into which it would have been born is oddly satisfying.

7. Geto Boys "Six Feet Deep" (1993)

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Album: Till Death Do Us Part

Producer: N.O. Joe

Label: Rap-A-Lot

Scarface's catalog, from his work with the Geto Boys to solo material, is littered with stories that detail the struggle of coming to grips with murder in the urban community. And while later records like "I Seen A Man Die" are certainly somber, the frank manner in which the stark reality of untimely death is addressed on "Six Feet Deep" makes it especially tragic.

6. De La Soul "Millie Pulled A Pistol on Santa" (1991)

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Album: De La Soul Is Dead

Producer: Prince Paul

Label: Tommy Boy, Warner Bros.

This tragic four-minute "girl who cried wolf" scenario feels like a short film onto itself. Gripping production from Prince Paul and detail-laced rhymes from the group heighten the tension with each verse. Millie's last ditch efforts to save herself from sexual abuse at the hands of her own father go unnoticed, and she winds up murdering him in cold blood, while he's working as Santa Claus at Macy's. But even when Millie gets her revenge, nothing feels right, and that is the lingering feeling associated with this record.

5. Wu-Tang Clan "Tearz" (1993)

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Album: Enter The Wu-Tang: 36 Chambers

Producer: RZA

Label: Loud

RZA raps about the death of his little brother. Ghostface Killah raps about a reckless friend contracting HIV. Both stories are told with such a painfully personal touch, and the record's haunting sample only accentuates it. RZA's verse hits especially hard, particularly when he succumbs to a shocked "Aw man!" rather than the word "dead" to describe his sibling.

4. Eminem "Kim" (2000)

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Album: Marshall Mathers LP

Producer: F.B.T

Label: Aftermath, Interscope

Eminem has a deeply visceral discography. He drives a fictional fan to murder and suicide on "Stan." He publicly blasts his mother's parenting skills on "Cleanin' Out My Closet." But no record of his is more disturbing than "Kim," in which he kills his daughter's mother (and her new boyfriend and stepson) of the same name. The sting of betrayal from his ex-wife leaves its mark all over the record—the chorus is an extended painful yelp—and even with the fact that none of this really happened in mind, the violence is still jarring.

3. 2Pac "Brenda's Got A Baby" (1991)

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Album: 2Pacalypse Now

Producer: Deion "Big D" Evans, The Underground Railroad

Label: Interscope

Between "Dopefiend Diner" and "So Many Tears," part of 2Pac's legend is his ability to tackle complex and difficult subject matter. The darkest moment in his catalog may very well be the narrative behind his first single. Inspired by a true story in the newspaper, 2Pac weaves a fictional plot about teen pregnancy and child abandonment that seared itself into the conscious of pop culture log before Teen Mom was on air.

2. Ghostface Killah f/ Mary J. Blige "All That I Got Is You" (1995)

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Album: Ironman

Producer: RZA

Label: Loud

Audio clips from The Education of Sonny Carson and a Jackson 5 sample enhance the atmosphere of this bitterly nostalgic record, which also served as Ghostface's debut solo single. It's part motherly tribute, part youthful angst, and all honest, blunt emotion.

1. The Notorious B.I.G. "Suicidal Thoughts" (1994)

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Album: Ready To Die

Producer: Lord Finesse

Label: Bad Boy

Death was a common theme in Biggie's music and never is it more chilling than on Ready To Die closer, "Suicidal Thoughts." Instead of mulling over lost loved ones ("Miss U") or speculating about potential assailants ("My Downfall"), Big turns the gun on himself due to mounting stress in what remains a shocking twist. Nearly two decades later, the song still evokes emotion like few others.

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