Skip to content
Hip Hop 50


In the shadow of the looming AI tsunami, unabashed inability stands as music’s final truth
Gross creative ineptitude is a fragile, endangered spirit, that when encountered, we must cheer and encourage. (Credit: BSIP/UIG Via Getty Images)

There have been plenty of mediocre, bad, and just plain terrible MCs throughout the history of hip-hop, most of whom have sucked in boring, passe ways — lack of writing, delivery and performance skills, weak imagination, poor vocabulary, forced trendiness. There have also been a select few rappers so much worse than not good: rappers who suck so badly that it’s truly fascinating — makers of music so unintentionally terrible that its unabashed passion and honest idiocy alchemizes into unique, priceless art, as mesmerizing as diamonds from the bedrock.

Music this imbecilic cannot be made on purpose. It is its own genre, inaccessible to most all creatives — no gifted nor trained musician can reproduce authentic wackness. These aren’t rappers aware that they suck but having too much fun to care, and they aren’t fake-sucking for web traffic: suck-trolling can be detected. These rappers suck naturally and massively, like black holes, and being born devoid of any sense of musical pleasantry, they remain forever oblivious. They’re simply God-awful—and we thank God for them!

In the shadow of the looming AI tsunami, unabashed inability stands as music’s final truth. Gross creative ineptitude is a fragile, endangered spirit, that when encountered, we must cheer and encourage as we would an ambling toddler. Continually writing, recording, and releasing piss-poor songs amidst social media bloodlust is one of the bravest, coolest things any artist can do. Their cluelessness about how profoundly lacking their abilities are is heart-breakingly beautiful.

If it’s not yet clear, we aren’t here to hurt and ridicule. If you’re here in such spirit, shame on you. Leave our celebration of the boundlessness of human creativity. Perhaps go and explore the songs’ YouTube comments, allowing the messages of joy and affection to wash away your venom. Resist judging such pathetic masterminds, attempt to enjoy what they enjoy about their music. Turn it up and celebrate.


Unknown, “Damn, Baby”

Easily our rarest best-of-the-worst (this is the song’s only known appearance online), the recondite wretch that is “Damn Baby” may be the worst song in three civilizations. The performer isn’t identified, so for sake of reference let’s call this gravel-gargling fool Carl. Aimless and sedated, Carl, falling in and out of sleep over a preset beat from a Casio my-first-keyboard. Eyes doing 360s, Carl, muttering like a fresh-concussed quarterback. “Aawwll these broads, aawll on the floor,” not so much spoken, but croaked. It’s a miracle no producer, friend or family member ever said “Woah Carl. Woah guy. Let’s just think this one through.”

The “Damn Baby” video is a travesty — that pregnant woman twerking in a corner store snack aisle while Carl murmurs about a stripper who “gotta get up early and do her homework.” (For the sake of all things dignified, we’ll assume she’s in college.) There’s a different stripper, twerking under police lights, there’s Carl, shirtless at the gas station, sedated as a horse dying on a racetrack, making Martian sounds while strippers stand on his new convertible. Dang, there’s Carl again, blank and lucid in a pool, murmur-rapping and pushing strippers underwater. It’s all pretty creepy, but whatever, the beat bangs and Carl is hard as a MF’er.

Wait now, what’s this? Take note of our hero’s Goonies tee, a shirt so remarkably out of place, honoring such a beloved piece of American cinema, that it stands to reduce the song’s suck. The fact this skeeze-ball likes Goonies risks tipping “Damn Baby” into “I guess it’s alright” territory, lessening the awfulness that makes it all so hall-of-fame-terrible, and defaulting it from our list. Not a chance, Carl’s thousand-yard stare and saucy, slow-mo smile keep this gem planted in “Seriously, wtf” realm.

Baby count money, Bounce it like monkey, Actin’ like a donkey, Ain’t nothin’ funny

Artist unknown

When I’m in a bad mood I come here!….lmao I love this!!

Truly inspiring. Now I have a reason in life to wake up 4 min early and listen to this.

That beat is a masterpiece, listen to that time signature, it has a mind of its own!


Riak,  “How You Want Me To”

Here lies a ponderous abuse of consciousness: one of the most bizarre songs in hip-hop history. Listening to “How You Want Me To” can, well…make you feel stupid. It’s in the air. Riak is completely unintelligible. Stuck in a loop of random out-loud thoughts, he seems to be confusing himself. Less than four full sentences happen in the song, the rest, just a sputtered mess of letters and sounds that Riak must think means something. In fact, he doesn’t rap one full bar in this video — have we a Milli Vanilli?

A second listen begs a larger question—is Riak conscious, does he know who and where he is? Is Riak real? Have dark web click-farmers AI’d a zombie-Manute Bol to fascinate viewers and mine data, and if so, is his battery running low? If not for the beautifully smooth skin he could be taken for a zombie exploring Xanax. Is he blotto incommunicado, a failed installation of Elon’s Neuralink brain-chip? He could be an animatron, a stick-thin MC Chuck E. Cheese.

The video reveals no further truths. Stumbling through Crip-walks down an empty alley in a basketball-sized fitted cap and tee capable of drowning him, wobbling in front of a green-screen full of Windows stock desktop photos, shirtless and distressingly gaunt with a navel-length rose gold bike chain, Riak is an odious enigma, and “How You Want Me To”, his deific abstract masterpiece, is concrete proof of God’s vivid imagination.

You need to see you, keep my promise, come on and make families
Got to ask, don’t leave when you need me, its doggystyle


YouTube comments disabled.


TBaby, “It’s So Cold in the D”

There’s no trivializing the song’s subject — friends who died too young in the streets of Detroit. That’s not funny. But a slam poetess with orange-pink dreads going so hard she ignores time, bulldozing 4/4 beats with postmodern full-sentence rap, rhyming couplets be damned — that’s sidesplitting. Look, vocalizing outside the lines is one thing. Contrapuntal vocal patterns are another. But rapping against the beat at length without noticing, ignoring every tenet in the world of Western music, clashing with the natural sapien sense of rhythm, those are different things entirely. “It’s So Cold…” sucks in these ways and more, and it’s immensely enjoyable.

Witness TBaby’s aharmonic, dreadfully off-key singing — the type that causes babies to grimace, dogs to cock their heads, and bird flocks to migrate out of season — and don’t try and deny it: it’s badass. Rapping meters off-beat with the floor-flat, emotionless inflection of Stephen Hawking’s voice box (RIP king!) — that’s badass too. Two pillars of pop culture agree: Beavis & Butthead watched the video on their recent reboot, with a lot of silence and confusion, plenty “Uhh” and “Ehh”, and ultimately, “This rules!”

After going viral, TBaby re-recorded the track in 2015 at a proper studio with skilled musicians (and hella autotune), got herself a Mary J. Blige makeover, and shot a snazzy new video. To no surprise, neither redress could match the egregious majesty of the originals (Reminder: Orchids can’t be 3D-printed). Nonetheless, the fact that TBaby persisted as an artist long enough to make pro-level versions is an Everest-level conquest.

Playing drinking games and shit, Always into big thangs and shit, Shit was getting wicked and shit


Almost 2022 and I still sing this masterpiece in my head

From the terrible studio engineering to the weird visual team and videographer, this song will forever be a CLASSIC. The story and societal impact of the D will forever be recognized!


Reh Dogg, “Why Must I Cry”

So many questions. Why does Reh Dogg sound like a sad third-grader reading a poem in class, how does every song he’s ever made sound like he’s never seen the lyrics before? What’s the story with the “Why Must I Cry” montage video, featuring Reh Dogg rapping sudsy (effective loofah by the way), nude and crying in a shower, then tumble-rolling with pants on into a living room, grabbing a clip off the carpet and loading a gun? Why running backwards down a hunting trail through fog in the winter, high-knee prancing in the wilted brush? Because Reh Dogg is a fucking genius is why.

Granted, “Why Must I Cry” is viral detritus, and Reh raps like a mute man discovering speech. It’s also a moving, nude-souled simpleton’s tale of kindness exploited, a tear-soaked testament to the rigors of maintaining the emotional vulnerability required to be loved. Hip-hop this fearless and mature is more than scarce, and its bizarre video, a metaphorical vision of Reh Dogg’s splintered relationship with a young fatherless boy he tried to befriend and guide, but who instead stole his jewelry and firearm, is a lo-fi, Lynch-ian treasure.

The sob-rap continues. With a face like Kanye during glycemic swelling, Reh tells of a baby momma denying him custody time, and another woman about to birth his twins, and a mall security job he hates. It’s no surprise he’s crying in the shower. We’ve all done it, it’s a satisfying heart-cleanse. But he could’ve adjusted the camera angles — it’s almost full-frontal in a few of them. Once “Why Must I Cry” invaded society in 2006, Reh went bonkers, tracking and releasing nearly 1,000 songs on YouTube, but thankfully, despite rapping for nearly twenty years, he hasn’t grown the least bit better.

Why must I cry? Why must I cry? Why?
Why must I cry? Why must I cry? Why?

Reh Dogg

Kneeling in awe, I am humbled by the sheer brilliance of this masterpiece. With each shower, this song becomes an essential part of my ritual, for without it, life loses its vibrance and meaning.

I’m going through a hard time right now and your songs give me the confidence to go on. Really inspiring, your words really mean something.


Bangs, “Take You to the Movies”

After Jimmy Fallon ridiculed Banks’ viral hit “Take You to the Movies” on Late Night… (daring, given Jimmy’s predilection for blackout-drunk Manhattan karaoke), the glad-hearted MC shouldered the ridicule and went for broke, recording “Take you to Starbucks”, “Take you to Burger King”, “Take You to KFC”, and “Take You Shopping”. As can be surmised all are certainly wack, but none so much as the original, the video for which finds Banks sprawled on zebra-skin blanket, texting on an iPhone 2, batting broken raps around like cats do half-dead mice.

Patchwork sentences, inverse intonations, rhymes nowhere in sight — the man sucks at rapping, fantastically. Behind Banks’ lingual molestation floats the “Take You to the Movies” beat, the defining sound of all things cheap and fluorescent—a blinking neon license plate frame, hold music at a discount orthodontic clinic, a ghost-town-empty ‘90s food court, pick your bright pink poison.

Cheese and folly aside, “Take You to the Movies” should be praised for its thoughtful intentions and respectful tone. In a genre full of misogynist slurs and sexual incivilities, Banks offers to take a woman on a traditional paid date (He says he bought the popcorn already.) Banks himself seems trustworthy, but keep your guard up when listening, as the song is maliciously catchy, sure to take up squat in your unconscious, and emerge when you’re trying to work or make love.

I’m a different guy, coming from the sky, nothing to worry about
Hold the popcorn and the drink, let me pay the money so that we can get in


This is probably the most respectful rap song towards women, a lot of rappers can learn a thing or two from your boy Bangs

I come back whenever life gets hard



John Earle the Spinner Man, “Big Money”

While the song isn’t especially atrocious, the “Big Money” video is: A dollar store George Foreman, a giant spinning hubcap on his necklace, skeezy and winded in shin-length jeans shorts, rhyming about crack, sex and murder on a kids’ cable access show. He’s Spinner Man! Blowing dollar-store pop & lock combos, making perv faces while ten third-graders dance backup, Spinner Man! Forgetting the words to “Cuttin up bricks, choppin down O’s”, manually spinning the huge tire rim swinging from his neck (then spinning it again, he’s pretty proud of it.). Doing the Dougie into the Egyptian, trying the Worm and flopping out, yelling “Say no to drugs kids!”, it’s Spinner Man!

This has to be a skit, except it isn’t. “Big Money” is an actual song, a crass bastardization of the Cash Money mold, and Spinner Man is John Earl, a parking-lot pervert version of Cash Money CEO Birdman. Earl released the song as titled in 2010, then renamed it “Big Money Trap Star” and released it again the next year, with a “real” video featuring the requisite cussing, gun talk and crack-cooking visuals. “Wake Yo Ass Up” was to follow, an inspirational piece decrying gluttony and over-dependence on public assistance, its video featuring Spinner sleeping on a couch outdoors while children run by and spin his wheel. Props due to Mr. Earl, sacrificing his neck health for our enlightenment.

Got you blowin up
Like you swallowed a hand grenade
Got the toilet paper
Because you know you the shit

John Earle the Spinner Man

Every time i’m depressed I come here and get a boost. Song of the century.

Give the man a record deal like yesterday. Fire!

This dude was actually ahead of his time. This is literally music today, and the listeners.