Sadboys: The Saddest Rappers & Their Saddest Songs

I don't know where you were when the sad wars hit, but if Yung Lean and his Sad Boy affiliates ushered in an era where 15-year-old Swedish kids crying over pokemon cards, clad in North Face, are spawning articles in swanky East Coast outlets, now seems like the time to honor the tradition of hip-hop tear jerkers that broke your heart but didn't actually make you cry that one time. That was just something in your eye, right? No, it was allergies, wasn't it?

Alright, whatever. The point is that the lyrical nature of rap makes for some heart-wrenching confessionals. We like our rappers to be bad-ass, sure, but if they never creep up from under the shell of super-sized hip-hop braggadocio and tough-guy bullshit with all the pathos of a cartoon lampooning the general public image of a rapper, we tend not to remember them all too well.

Fortunately, we've waded through some of the most thoroughly depressing bars out there, giving you the opportunity to feel pretty horrible too. Without further ado, here's a list of a few of the saddest rappers and their saddest songs that will leave you wallowing in your own misery more than some sweater-vest wearing nerd from the eighties ever did when listening to Morrissey croon ambiguous bummers.

Let us know what we got right and, let's face it - this is more tempting, what we missed.

Wait, Chance isn't sad, right? He's the spitting human equivalent of unrestrained jovial expression, isn't he? Well, I disagree. Chance's debut mixtape will go down as one of the greatest mixtapes ever released, and as enthusiastic and bat-shit hyper as most of these tracks are, there is an undercurrent of deep melancholy throughout the record that all bubbles up to the surface when the penultimate track, "Acid Rain" hits.

The track itself sets the mood with dark synths and a strings loop, as Chance flips, as he does so expertly, between fantastical druggy imagery and the doldrums of biting nostalgia and self-reflection. He's thinking about school, the uncertainty of his future, fucking around with his friends like all twenty-year-olds do, but it's marked, as everything seems to be, by the murder of his best friend which he witnessed not too long ago.

"My big homie died young; just turned older than him/ I seen it happen, I seen it happen, I see it always/ He still be screaming, I see his demons in empty hallways"

This is a common phenomenon when your high school is in inner-city Chicago and it's a miracle that Chance remained sensitive and impressionistic without withering underneath a shell. He comments on the violence in a seering, snarling manner that makes your toes curl.

"Sometimes the truth don't rhyme/ Sometime the lies get millions of views/ Funerals for little girls, is that appealing to you?/ From your cubicle desktop, what a beautiful view"

Kid Cudi - "Solo Dolo"

When Kid Cudi stamped his wrists with that embarrassing and annoying tattoo of suicidal slit marks, he became the poster kid for depressed back-packin' rappers. But before he became a parody of himself, he penned numerous depressing diddies. Off the top of our heads, we have "Solo Dolo" from his signature Man On The Moon album.

"Listen Good/I don't have nobody/ But what I might feel all the sounds of sanity/Hoping what I hear, loops itself continuously/Then I won't be afraid"

These lines, opening over a seriously moody soundscape, soundtracked many of our darkest moods back in high school or college, wherever you were at when Cudi hit. "Solo Dolo" seems to track the actual chords of self-pity, but it also made you feel less isolated by depression whenever he came up on the ear-buds, and if you were a moody fuck like me that was all the time. On repeat.

Kanye has numerous sad songs as he's always been somewhat of a sad sack. He has a tear-inducer about his mom and even made an entire album devoted heartbreak, but "Blame Game" off My Beautiful Dark Twisted Fantasy may be one of his most effective.

Perhaps it's the heart-wrenching prepared piano loop courtesy of the always phenomenal Aphex Twin, or it could be the fact that the track showcases the best distillation of Kanye's stream-of-consciousness style, because it's definitely not the Amber Rose related subtext which may or may not be a product of our imaginations.

Either way, it's a doozy.

"On a bathroom wall I wrote/ I'd rather argue with you than to be with someone else/I took a piss and dismiss it like fuck it and I went and found somebody else/Fuck arguing or harvesting the feelings, I'd rather be by my fucking self/Till about 2am and I call back and I hang up and start to blame myself/Somebody help"

Who hasn't felt this way at some point? Maybe one of the downsides to Kanye's no-hold-barred unfiltered approach is the unrelenting ego portion (although that I find integral and doesn't bother me in the slightest) but the upside is when you get something this raw and honest, as Kanye's oft wont to do.

Strangely enough, the track ends on a funny note with a fictitious voicemail recording brought to us by the hilarious Chris Rock. Check it out.

Tyler may seem like the epitome of pratfalls, fake beards and nonsensical, esoteric euphemisms if Loiter Squad is all you have to go by. If you listen to his music, even if you're not the biggest Odd Future fanboy out there, then you know Tyler just *won't* lighten the fuck up. Not about girls, not about his daddy abandonment issues, not about being famous, but to his credit he eased up on the murder/rape fantasies as he got a little older and wiser. Not to diss Tyler in the slightest, he's incredibly talented and funny, an excellent producer and a seriously depressing lyricist.

"My father died the day I came outta my mother's hole/And left the burden on my soul until I was old enough/To understand that the fuckin' faggot didn't like me much/He loved my moms enough to bust a nut and then he shake Junt/Bringin' pops to school today for twelve years I cheated/Told the fuckin' faculty that he was at a meeting and/Bring that dude to life then he wasn't at the meeting"

And that's how the track *starts.* If your memory needs some jogging, that's "Inglourious" off his Bastard debut. It might be one of the starkest examples of just how fucked up and sad Tyler was during this time-period even if he masked it with goofy antics.

You might not be familiar with Cage but let me explain why he gets an appearance on "The Saddest Dudes in Rap" list. His father was a major heroin dealer and addict, dishonorably discharged from the military, who was extremely physically abusive to the young Cage and his mother that it could be more accurately described as torture. If it couldn't get any worse, as if there were some cosmic joke being played at his expense, his father's name was Bill Murray, of no relation, obviously, to THE Bill Murray.

But things got better when he started rapping, right? Well, they might have if Cage didn't develop a dangerous PCP addiction and tended to attempt to off himself at every chance he could get. He was eventually held in a mental ward where he had to be restrained as he kept on attempting to tear out his arteries with his teeth. Cage reflects on his lovely childhood in the song, "Stripes."

"Beer cans and cigarette butts cover the floor day/Half gone, he sleeps, scared pregnant teen in the doorway/Watching him sleep clutchin' her belly, little feet kick to send the teen back to the toilet, spent her last week sick/ when little Billy feed her ground up Jesus powder/ would've beat her louder if it would've pushed the fetus out of her"

Holy Shit.

A little while back, at the age of nineteen, with a burgeoning career in hip-hop ahead of him, Capital Steez jumped off a building robbing Pro Era and all the Beast Coast affiliates of their most promising inductee. Maybe this isn't fair, but hindsight elevates the lovely and melancholy "Emotionless Thoughts" to heartbreaking levels. 

It's pretty bleak but all of the Steez' tracks were dark. Strangely enough, it's the sweetness and commonality of the track that makes it so wrecking. Girl problems? Everyone's had girl problems, but Steez had such a way with his pen that it feel different, both new and familiar. 

"And I'm the bad guy yet again/Spend so much time trying to find who the victim is/ And if we put it in the eyes of the witnesses/ I still get the blame for fucking up and beginning shit"

RIP Steez.

12-year-old Brenda has got a baby, and with that 2pac penned a story for a track that spoke bluntly about a topic that was especially uncomfortable in the early nineties. This song showcases Tupac's two biggest strengths; his knack for making white people squirm a little bit and his knack for storytelling. 

This is what made the pathos of Tupac so fascinating to everyone and it explains why he's so exalted currently. It was the moments that he transcended the gangster image to talk about real problems, often of the socio-economic inequality kind. 

Tupac never tackled a subject so thoroughly dark as the Brenda story. A young girl gets pregnant, can't raise the kid, tries to sell crack, and then the story starts to get bleak.

"Went in death to his arms, it's sad/Cause I bet Brenda doesn't even know/ Just cause your in the ghetto doesn't mean ya can't grow/ But oh, that's a thought, my own revelation/ Do whatever it takes to resist the temptation/ Brenda got herself a boyfriend/ Her boyfriend was her cousin, now lets watch the joy end/ She tried to hide her pregnancy, from her family/ Who didn't really care to see, or give a damn if she/ Went out and had a church of kids/ As long as when the check came they got first dibs"

You knew Eminem would creep up on this list at some point and you probably knew which song too. I mean, it's hard just picking one - when Eminem's not the poster boy for unbridled rage, he's marked for his sound of acute depression. "Stan", however, veers from the autobiographical to a lyrical fantasy and it stands as one of his best songs and one of the saddest tracks ever made.

We all know the story the song paints by now. If not, spoiler alert: it starts from the perspective of a crazed fan by the name of Stan writing Eminem in a letter. The letter goes ignored and it becomes apparent that Stan's mental state is deteriorating and probably was pretty bad to begin with. That's all until the coup d' grat when it's revealed that Stan tied up his pregnant girlfriend into the back of his car and drives off a bridge. The caveat: Stan was inspired by Eminem's violent lyrics. Even though Eminem writes back in the song, it's too late.

"That's kinda how this is, you coulda rescued me from drowning/Now it's too late - I'm on a 1000 downers now, I'm drowsy/ and all I wanted was a lousy letter or a call/ I hope you know I ripped all of your pictures off the wall/ I love you Slim, we coulda been together, think about it/ You ruined it now, I hope you can't sleep and you dream about it/ And when you dream I hope you can't sleep and you SCREAM about it/ I hope your conscience EATS AT YOU and you can't BREATHE without me/See Slim; [*screaming*] Shut up bitch! I'm trying to talk!/Hey Slim, that's my girlfriend screaming in the trunk/but I didn't slit her throat, I just tied her up, see I ain't like you/ cause if she suffocates she'll suffer more, and then she'll die too"

This vibrant lyricism mixed with a haunting sample from Dido brings us the Eminem masterpiece we know today. Unlike some of his other old material that seems a bit more trite now, "Stan" still carries it's impact, as if we just heard it.

Darkness cribbed Biggie his entire life, dogging his step. It's not a bad thing, it's what made him great. He was a complicated fellow and his music only benefits from that.

Take the thoroughly depressing "Suicidal Thought" under consideration, the epic closer for the seminal album cheerily called Ready To Die. The song's framing device is that of a phone call Biggie's making to his friend in the form of a suicidal confessional. It is utterly and thoroughly depressing shit.

"When I die, fuck it I wanna go to hell/ Cause I'm a piece of shit, it ain't hard to fuckin' tell/ It don't make sense, goin' to heaven wit the goodie-goodies/ Dressed in white, I like black Tims and black hoodies/ God will probably have me on some real strict shit/ No sleepin' all day, no gettin my dick licked/ Hangin' with the goodie-goodies loungin' in paradise/ Fuck that shit, I wanna tote guns and shoot dice/ All my life I been considered as the worst/ Lyin' to my mother, even stealin' out her purse"

The Sad Boys coverage talks about a new movement, one where sadness is now glorified rather than shunned. There's nothing new about that. Okay, white kids from Sweden openly crying on tape while giving their best Lil B impersonation whilst repping 2003 and Digimon is entirely new for hip-hop. But raw sadness isn't. It's been there always, just look back at the beginning, when the OGs still roamed, and Brooklyn wasn't the artisanal cupcake mill for white hipsters in floral print that it eventually became. 

We couldn't leave off one of the first rappers to bring emotions to the forefront, Drizzy Drake. While Drake's music isn't necessarily sad in the same way as some of the other rappers on the list, we often find Drake in an openly emotional state on his records. Whereas some of the rappers on the list paint a bleak picture about daily life or their childhood and thus give us sad or depressing music, Drake seems to be in a permanent state of heartbreak, which is where his sadness comes from. And so the Toronto native has often been called "soft". He isn't afraid to lay down bars dedicated to his mom and grandma (on "Look What You've Done"), and equally, he's not shy about putting on wax his true feelings for any particular lady, even if they are not reciprocated (and that is often the focal point). He's also unashamed about drunk dialing, as he sings on "Marvin's Room",

"Cups of the Rosé/ Bitches in my old phone/ I should call one and go home/ I’ve been in this club too long/ The woman that I would try/ Is happy with a good guy/ But I’ve been drinking so much/ That I’ma call her anyway and say/ 'Fuck that nigga that you love so bad/ I know you still think about the times we had'/ I say, 'fuck that nigga that you think you found / And since you picked up I know he’s not around'"

Despite being labeled as "soft" for this song and many others like it, Drake strikes a chord with many of us which is why he's got so many fans. His music is relate-able, as are the overtly human emotions he puts into the music.

And now for what you've all been dying for. Yung Lean. 2003. Charizard blast burning through these grass type motherfuckas. Blue-Eyes-White-Dragons in Sweden. Forever.