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 Plusnotably 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. 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? So we decided to round up the most depressing hip-hop songs of all time. To keep things diverse, we strived to limit the selections per artist. After all, rappers who excel at making sad music often do it repeatedly, and a list filled with only Scarface or Juice WRLD tracks wouldn’t be nearly as interesting.
Here are the 50 most depressing rap songs of all time.
(Originally published on 03/06/18)
50.Lil Baby, "Emotionally Scarred" (2020)
Producer: Twysted Genius
Most depressing line: "I ain't got nothing against you, we human, we all got issues/But I'm tired of being tired of being tired/That part of me done died"
Days before releasing My Turn, Lil Baby conducted an interview with the New York Times, where he said: “I don’t miss my old life at all. Period.” That feeling sits at the heart of the album’s centerpiece, “Emotionally Scarred.” Driven by somber guitar chords, the usually swaggering Baby reflects on growing up in the streets and rising into one of the biggest stars in the world. The track opens with: “A love letter came through the mail, it said, ‘I miss you.’ I ripped it up and flushed with the tissue, tried to forget you.” Many artists try to hold on to where they came from, but Baby had to let go of his past in order to chase success. —Antonio Johri
49.Nino Paid, “Joey Story” (2025)
Producers: Deyflo, 1keep and Tre Webb
Most depressing line: "He cocked the pistol back and put that bitch up to his chin/And then he put one in his own head"
DMV rapper Nino Paid has built a cult following through his deeply personal, highly emotive songs. His most well-known track, however, isn’t autobiographical—it’s a devastating narrative that captures a man’s final moments before suicide. Nino Paid writes with a level of detail and emotion that legendary rappers in a similar vein—think Scarface or The Notorious B.I.G.—would admire. —Dimas Sanfiorenzo
48.Baby Keem, "issues" (2021)
Producers: Baby Keem & Jahaan Sweet
Most depressing line: "My sister Ree-Ree only see me on the screen/ I know she needs me, I can't help but feel T"
“Issues” is easily the most personal song on Baby Keem’s The Melodic Blue. The track captures his ruminating mind as he unpacks his complicated relationship with family and the remorse that lingers. —Dimas Sanfiorenzo
47.Boosie Badazz, “Smile to Keep From Crying” (2016)
Producer: Chophouze
Most depressing line: "Sometimes, I need me a friend, I have no one to call/I need me somebody who listens, maybe I need me a dog"
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.
46.Meek Mill Feat. Young Thug, “We Ball” (2017)
Producer: Future & Wheezy
Most depressing line: "When they killed my nigga Snupe, I seen my young nigga/In the casket he ain't even have no blood in him/ Prolly the reason why I keep taking these drugs quicker"
In which Meek Mill—one of the electrifying rappers of the last 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.
45.A Tribe Called Quest, "8 Million Stories" (1993)
Producer: Skeff Anselm
Most depressing line: "Woe is me, I'm havin' problems"
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.
44.Mac Miller, "Perfect Circle / God Speed" (2015)
Producer: Ging
Most depressing line: "Yeah, blame the drugs, got me sinnin' on a weekday/Drunk as fuck, do a buck sixty on the freeway/Givin' y'all the freebase, hidden in the middle of a briefcase"
Throughout the 2010s, no rapper evolved quite like Mac Miller. He went from Big L–inspired showcases to frat-party anthems to avant-garde, introspective jazz rap. GO:OD AM captures him in the middle of that journey. Much of the album reflects his struggles with addiction and stints in rehab, but on “Perfect Circle / God Speed” he’s at his most lucid and in-depth. It’s a tough story, made even harder by the way it foreshadows his end. —Dimas Sanfiorenzo
43.Earl Sweatshirt Feat. Na’kel, “DNA” (2015)
Producer: randomblackdude
Most depressing line: "I got a couple bitches now, I ain't gotta lie 'bout that/I know you in a better place, I can't even cry about that"
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.
42.Company Flow, “Last Good Sleep” (1997)
Producers: El-P & Mr. Len
Most depressing line: "Huddled up clutching sis I think I heard a dress ripping/I should've reacted to that"
After spending the album unspooling tangly rhymes over septic beats, Company Flow started 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."
41.Lil Uzi Vert, "XO Tour Llif3" (2017)
Producers: TM88 and JW Lucas
Most depressing line: "Should've saw the way she looked me in my eyes/She said, 'Baby, I am not afraid to die'/ Push me to the edge/All my friends are dead, push me to the edge"
Plenty of the SoundCloud boom of the mid 2010s, was knocked for its vibe-driven music. But the emo rap wave—led by XXXTENTACION, Trippie Redd, and Lil Uzi Vert—helped bring hip-hop back to its storytelling roots, centering songs around personal turmoil and emotional struggle. Lil Uzi Vert emerged as one of the pioneers of emo-trap, crooning in autotune about feelings many rappers avoided confronting directly.
His breakout anthem, “XO Tour Llif3,” is both his biggest hit and his most heartbreaking. Despite its infectious chorus dominating every internet-connected device in 2017, the song grapples with Uzi’s troubled relationship with then-girlfriend Brittany Byrd, and the suicidal thoughts she felt as their romance unraveled and ultimately fell apart. —Antonio Johri
40.Future, “Perkys Calling” (2016)
Producers: Southside and DZL
Most depressing line: "I can hear the purple callin'/I can hear the Perkies callin'/I can hear the purple callin'/I can hear the Xannies callin'/I can hear them Percs callin'"
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.
39.Vince Staples, “Summertime” (2015)
Producer: Clams Casino
Most depressing line: "I'm searching for atonement, do I blame my darker tone?/I know some things are better left unsaid and people left alone/Pick up the phone/Don't leave me alone in this cruel, cruel world"
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.”
38.Lil Durk Feat. Gunna, What Happened to Virgil (2022)
Producer: Chopsquad DJ
Most depressing line: "Oh my God, what happened to Virgil?/I wish my brother had made it out surgery"
On “What Happened to Virgil,” Lil Durk and Gunna turn the tragic death of fashion icon Virgil Abloh into a meditation on loss. For Durk, that grief is painfully personal: his close friend King Von and his brother DThang were killed within seven months, both in devastatingly public ways. The track is steeped in melancholy, and its central refrain carries an eerie, almost ironic weight—especially given how “what happened to Virgil” later became a viral TikTok meme. Even so, it endures as one of the most haunting rap songs in recent memory. —Antonio Johri
37.Immortal Technique, "Dance With The Devil" (2001)
Producer: 44 Caliber
Most depressing line: "So Billy stomped on the bitch until he'd broken her jaw/The dirty bastards knew exactly what they were doin'/They kicked her until they cracked her ribs and she stopped movin'"
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.
36.Pete Rock & CL Smooth, "They Reminisce Over You (T.R.O.Y.)" (1992)
Producer: Pete Rock
Most depressing line: "T to the R the O-Y, how did you and I meet?/In front of Big Lou's, fighting in the street/But only you saw what took many time to see/I dedicate this to you for believing in me"
"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.
35.Polo G, "Deep Wounds" (2019)
Producers: 1040, D. Major & Callari
Most depressing line: "I miss Mike Durb, I won’t forget the things you used to say/My friends got killed on the same block where we used to play"
When Polo G is at his most effective, he raps with vivid, matter-of-fact directness. The effect is striking: he describes deeply emotional experiences in an almost detached tone. Die a Legend is full of somber songs, but “Deep Wounds” is the most devastating. Its melodic delivery and calm demeanor might suggest something lighter, but lines like “I pop so many pills, shit got me losin’ weight” and “That pain was so unbearable, I almost gave up” make clear just how heavy it is. —Dimas Sanfiorenzo
34.Cam'ron Feat. Brotha, "D Rugs" (1998)
Producer: Darrell "Digga" Branch
Most depressing line: "You know my mother, her nostrils wide/Too much of D Rugs left her hospitalized/We both was arrested, stars of the block/Her by cardiac, me by the cops"
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.
33.Saba, "PROM / KING" (2018)
Producers: Saba, daedaePIVOT and Daoud
Most depressing line: "Sometimes, I fucking hate Chicago 'cause I hate this feeling/ Innocent niggas get shot at in the broad day, the a.m."
In February 2017, Chicago rapper dinnerwithjohn was stabbed to death. He was only 24 years old. A year later, his cousin Saba released Care for Me, an album that serves as an ode to the Pivot Gang co-founder. The most devastating track is “Prom / King,” a gripping story about a prom date Walt set up for him that takes a tragic turn. It’s Saba at his best—grief-stricken, rapping in an almost possessed, emotionally raw manner. —Dimas Sanfiorenzo
32. Kendrick Lamar, “u” (2015)
Producers: Sounwave, Taz Arnold and Whoarei
Most depressing line: "And you the reason why mom and them leavin'/No, you ain't shit, you say you love 'em/I know you don't mean it I know you irresponsible, selfish, in denial, can't help it"
“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.
31.Jay-Z Feat. Beanie Sigel and Scarface, “This Can’t Be Life” (2000)
Producers: Kanye West
Most depressing line: "Now as I walk into the studio to do this with Jig'/I got a phone call from one of my nigs/Said my homeboy, Reek, he just lost one of his kids/And when I heard that, I just broke into tears"
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.
30.Trippie Redd, "Underwater FlyZone" (2018)
Producer: WE ARE THE STARS
Most depressing line: "I don't have anyone to cry with or to die with
I die on my own"
Breakups are hard, and over the years rappers have gotten better at dropping the veneer and speaking more honestly about the pain that comes with the end of a relationship. “Underwater FlyZone,” from Trippie’s debut album, Life's a Trip, is particularly devastating—largely because of the raw vocal performance, with moments where he’s outright screeching. Backed only by a soothing guitar and no drums, the track shows just how effective the emo side of rap can be. Heartbreak, after all, is a normal part of life. —Dimas Sanfiorenzo
29.Kid Cudi, "All Along" (2010)
Producer: Emile Haynie
Most depressing line: All along I knew I was meant to be alone Out there on my own, yeah
There have been countless songs about depression, but few capture the feeling as effectively as Kid Cudi’s “All Along.” It’s a bleak, messy portrait, with junk food scattered around and hopelessness hanging heavy in the air. Originally meant to close out Cudi’s sophomore album, Man on the Moon II: The Legend of Mr. Rager, he ultimately moved it up in the tracklist—partly because it was too much of a bummer to end the album this way. —Dimas Sanfiorenzo
28.Dr. Dre Feat. Mary J. Blige and Rell, "The Message" (1999)
Producer: Lord Finesse
Most depressing line: "I miss you, sometimes I wish I just died with you"
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.
27.Lil Wayne, “I Feel Like Dying” (2007)
Producer: Jim Jonsin
Most depressing line: "I am a prisoner locked up behind Xanax bars"
Even Lil Wayne had to open up about his personal struggles during his commercial peak. 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.”
26.Organized Konfusion, "Stray Bullet" (1994)
Producer: Organized Konfusion
Most depressing line: "'Cause for some little girl she'll never see more than six years of life Trifleing, when she fell from the seesaw"
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.
25.Nas, "Dance" (2002)
Producer: Chucky Thompson
Most depressing line: "I wish you were here, I miss you more each second I breathe/You resting in peace, forever, I accepted you're free"
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.
24.Ice Cube, "Dead Homiez" (1990)
Producers: Sir Jinx, Chilly Chill and Ice Cube
Most depressing line: "Another homie got murdered on a shakedown/ And his mother is at the funeral, havin' a nervous breakdown"
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.
23.Rod Wave, "Dark Clouds" (2019)
Producers: Mook On The Beats, Trillo Beats and Dave-O
Most depressing line: "I been feelin' pain for so long I done became numb"
What’s the saddest Rod Wave song? It’s like asking what the most violent King Von track is, or the best Pusha T drug-dealing song. Rod Wave has practically made sad songs their own genre, so picking just one feels impossible. Still, “Dark Clouds” stands out. It doesn’t only capture the struggles he faced before success—it also conveys the depression that came with life-changing fame at such a young age. In short: being Rod Wave is hard. —Dimas Sanfiorenzo
22.Lost Boyz, "Renee" (1996)
Producer: Mr. Sexxx
Most depressing line: "I gotta see what's going on/And by the time I reach the hospital, they tell me "Mr. Cheeks, Renee is gone"
"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.
21.Lil Peep, "the way i see things" (2015)
Producer: Kryptik
Most depressing line: "I don't feel much pain/Got a knife in my back, and a bullet in my brain/ I'm Clinically insane"
Lil Peep’s “the way i see things” opens with one of the most upsetting first lines in recent memory:
"I got a feelin’ that I’m not gonna be here for next year / So let’s laugh a little before I’m gone."
Peep did live past the next year, but he died of an overdose two years after the song’s release. The track distills the essence of his music: a bleak reflection on the mix of euphoria, numbness, and sadness that comes with addiction.
20.Kanye West, "Coldest Winter" (2008)
Producers: Jeff Bhasker, No ID and Kanye West
Most depressing line: "On lonely nights, I start to fade/Her love's a thousand miles away"
Kanye West’s 808s & Heartbreak is one of the saddest albums of the 21st century, with the rapper grappling with both the end of his engagement and the death of his mother. Much of the record dwells in heartbreak, but the closing track, “Coldest Winter,” feels like the song most directly for Donda West. It’s devastating—a track that builds and swells as Kanye grows more emotional.
19.Bone Thugs-n-Harmony, "Tha Crossroads" (1996)
Producers: D.J. Dre Ghost, DJ U-Neek and Bone Thugs-N-Harmony
Most depressing line: "Damn, man, I miss my Uncle Charles, y'all/And he shouldn't be gone In front of his home, what they did to Boo was wrong"
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.
18.OutKast, "Da Art of Storytellin' (Part 1)" (1998)
Producer: Mr. DJ
Most depressing line: "We on our back, starin' at the stars above/Talkin' bout what we gonna be when we grow up I said, "What you wanna be?" She said, 'Alive'"
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.
17.Jay Electronica Feat. JAY-Z, “A.P.I.D.T.A.” (2020)
Producer: Khruangbin
Most depressing line: "The day my mama died, I scrolled her texts all day long/The physical returns but the connection still stay strong"
Hours after news broke that Kobe Bryant and his daughter Gianna died in a helicopter crash, Jay Electronica and Jay-Z recorded the somber “A.P.I.D.T.A.,” which stands for “All Praise Is Due To Allah.” Jay-Z only performs the hook, delivering it in a labored, emotional manner we’re not used to hearing from the usually stoic rapper. While Jay Electronica provides a powerful verse reflecting on the deaths of those close to him, particularly his mother. —Dimas Sanfiorenzo
16.Puff Daddy Faith Evans & 112, "I'll Be Missing You" (1997)
Producer: Stevie J
Most depressing line: "It's kinda hard with you not around/Know you in Heaven, smilin' down"
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.
15.Jay-Z, "Song Cry" (2001)
Producer: Just Blaze
Most depressing line: "Shit, I'm a man with pride, you don't do shit like that/You don't just pick up and leave and leave me sick like that/You don't throw away what we had just like that"
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.
14.Ab-Soul, "The Book of Soul" (2012)
Producer: Tommy Black
Most depressing line: "You used to say that I could see the future/You was wrong, 'cause you was in it"
During TDE’s early years, one of the most prominent voices on songs was Carson singer Alori Joh, who was also in a romantic relationship with Ab-Soul. In February 2012, she died by suicide after jumping from a radio tower. Just a few months later, Ab-Soul honored her on his second studio album, Control System. Beyond the lyrics—where he tells the story of their love and tries to come to terms on why this happened—it’s the raw emotion in his delivery that lingers, with his voice cracking at points. To this day, it remains one of the most emotional songs in his catalog. —Dimas Sanfiorenzo
13.Juice WRLD, "Righteous" (2020)
Producers: Nick Mira and Charlie Handsome
Most depressing line: "Take a pill for the thrill, have a relapse/Devil in my head tryna run gym laps"
Juice WRLD’s music was always shadowed by addiction, heartbreak, and death, and “Righteous,” which came just a couple of months after his death, is no exception. From the very first lines, you can hear his voice tremble as he repeats “I will,” almost like he’s fighting back tears. That vulnerability set him apart. Drawing from the rock and indie bands he admired, Juice had a gift for pulling raw emotions out of anyone listening. When he sings, “taking medicine to fix all of the damages,” it lands with the weight of someone trying to heal while knowing it might destroy them too. —Antonio Johri
12.Common Feat. Lauryn Hill, "Retrospect for Life" (1997)
Producer: James Poyser and No I.D.
Most depressing line: "I'm sorry for takin' your first breath, first step, and first cry"
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.
11.UGK Feat. Mr. 3-2 and Ronnie Spencer, "One Day" (1996)
Producer: Pimp C
Most depressing line: "My man BoBo just lost his baby in a house fire/And when I got on my knees that night to pray, I asked God "Why You let these killers live and take my homeboy's son away?"
The first rap verse on UGK’s classic Ridin’ Dirty doesn’t come from Bun B or Pimp C but from Screwed Up Click member Mr. 3-2. His opening line—“Momma put me out, at only 14…”—sets the tone for a group not usually known for introspection. On “One Day,” the three rappers wrestle with death and the cruel randomness of it—like when Pimp C raps about a friend losing their child in a house fire. —Dimas Sanfiorenzo
10.The Last Emperor Feat. Poetic, "One Life" (2003)
Producer: Set Free
Most depressing line: "Moms and pops in the room, three or four docs in the room/ Test results suggest your colon and your liver Is so cancerous you got three months left/Me and Death is playing chess ever since then"
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.
9.Geto Boys, "Six Feet Deep" (1993)
Producer: N.O. Joe, John Bido and Tony Randle
Most depressing line: "The choir sung the songs that make us reminisce/And durin all the singing I broke down myself/When I looked and seen the family that my partner left"
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.
8.De La Soul, "Millie Pulled A Pistol on Santa" (1991)
Producer: Prince Paul and De La Soul
Most depressing line: "But when Millie and him got home, he was more of a villain/ While she slept in he crept inside her bedroom"
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.
7.Wu-Tang Clan, "Tearz" (1993)
Producer: RZA
Most depressing line: "I ran frantically, then I dropped down to his feet I saw the blood all over the hot concrete/I picked him up, then I held him by his head/His eyes shut, that's when I knew he was…/Aw man! How do I say goodbye?"
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.
6.Eminem, "Kim" (2000)
Producer: Bass Brothers
Most depressing line: "We could've—, hey, where you going? Get back here/ You can't run from me, Kim! It's just us, nobody else/You're only making this harder on yourself"
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.
5.XXXTENTACION, "Jocelyn Flores" (2017)
Producers: XXXTENTACION and potsu
Most depressing line: "I'm in pain, wanna put ten shots in my brain"
XXXTENTACION connected with people because he was a walking contradiction. On one hand, he was wild and abrasive, pushing kids to scream over distorted 808s on tracks like “LOOK AT ME!” On the other, he was seemingly fragile, pouring out his darkest thoughts. “Jocelyn Flores” captures that softer, depressive side. Built on a haunting Shiloh Dynasty sample, the track reflects on a girl in X’s life who tragically died by suicide following a falling out. The song is undeniably heavy, but X had a way of turning grief into something listeners could sit with, even find a bit of comfort in. —Antonio Johri
4.DMX, "Slippin" (1998)
Producer: DJ SHOK
Most depressing line: "Damn, was it my fault? Something I did? To make a father leave his first kid at seven doin' my first bid?"
DMX 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.
3.2Pac Feat. Dave Hollister, "Brenda's Got A Baby" (1991)
Producer: The Underground Railroad
Most depressing line: "He left her and she had the baby solo/ She had it on the bathroom floor and didn't know/ She didn't know what to throw away and what to keep/ She wrapped the baby up and threw him in a trash heap"
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 Feat. Mary J. Blige, "All That I Got Is You" (1996)
Producer: RZA
Most depressing line: "Check it, 15 of us in a three bedroom apartment/Roaches everywhere, cousins and aunts was there/Four in the bed, two at the foot, two at the head/I didn't like to sleep with Jon-Jon, he peed the bed"
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)
Producer: Lord Finesse
Most depressing line: "When I die, fuck it, I wanna go to hell/'Cause I'm a piece of shit, it ain't hard to fuckin' tell"
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. Three decades later, the song still evokes emotion like few others.