You know, when we think about classic cartoon
characters, there's like this comforting, built
-in expectation of invincibility. Oh, totally.
Like Wile E. Coyote. Exactly. A character runs
entirely off a cliff. They hang in the air for
a second looking at the camera. They plummet.
They create a massive, chaotic crater in the
ground. And then in the very next scene, they're
perfectly fine just dusting themselves off. Right.
It's hyperkinetic. It's incredibly colorful.
And crucially, nothing ever really hurts. The
damage is just an illusion. It's the ultimate
form of escapism. The consequences are entirely
temporary, and the chaos is generated purely
for our entertainment. But what happens when
you take that exact hyperkinetic, invincible
cartoon energy, apply it to a real -life musical
movement, and then real life, with all of its
brutal, irreversible permanence, actually crashes
in? Yeah, that is a heavy transition. It is,
because today's Deep Dive is exploring the Wikipedia
page of a figure who lived exactly that impossible
duality. We are looking at the life, the meteoric
career, and the profound resilience of Stokely
Cleavon Goldborn. Who you listening almost certainly
know better by his stage name, Ski Mask the Slump
God. Right. It is a remarkable heavy story to
analyze because for you the listener This isn't
just like a standard music biography where an
artist releases a few albums and wins some awards
No, not at all. This is really a real -time case
study on how highly localized completely unpolished
internet movements can suddenly morph into global
phenomena. It really is. And, perhaps more importantly,
it's a deep exploration of the immense psychological
toll that comes when sudden stratospheric fame
violently collides with devastating personal
loss. And our mission for this deep dive is to
explore that exact tension. Like how does an
artist who essentially helped invent the wildly
colorful hyper energetic subgenre known as meme
rap navigate a personal life that became defined
by incredibly public tragedy. It's an almost
unimaginable juxtaposition. You have this candy
colored internet troll aesthetic on one side
and some of the absolute darkest realities of
the human experience on the other. Okay, let's
unpack this from the very beginning, because
the origin story here is dripping with unbelievable
irony. Oh, the irony is thick. Right. So Stokely
was born in 1996. He grew up in Fort Lauderdale,
Florida. And the spark that essentially ignites
his entire career and frankly, a massive chunk
of 2010s hip hop culture. He's around $10 worth
of weed. Around $10 worth of weed. I mean, it
really is the ultimate butterfly effect. A completely
microscopic event reshaping a massive industry.
It reads exactly like a comic book origin story.
In 2013, he gets sent to a juvenile detention
center over this tiny, almost negligible amount
of marijuana. Which is crazy to think about.
It is. And it's inside that lockdown facility
that he meets another teenager during time. And
that kid happens to be XXXTentation. Yeah. You
have these two rebellious kids meeting in a high
-stress environment. And according to the sources,
their initial plan for when they got out wasn't
to take over the music industry. Not at all.
They were actually planning to commit home invasions.
Which serves as a very stark reminder of the
socioeconomic realities these teenagers were
facing. The trajectory they were on was incredibly
dangerous. Absolutely. But instead of going down
that path of escalating criminality, they pivot.
They start making music together upon release.
And what's fascinating here is the musical foundation
that Stokely Ski Mask already had built up before
he even met X. Right, because it wasn't just
a sudden random decision to try rapping. Exactly.
It wasn't just raw, unguided aggression, was
it? He actually had technical chops from day
one. He really did. Yeah. He is of Jamaican descent.
And his parents constantly played Jamaican music
in the house, exposing him to very specific complex
rhythm. Oh, that makes a lot of sense. But more
directly, his father was actually a rapper himself,
operating under the stage name Sin City. Sin
City, got it. And his dad didn't just casually
encourage him or like buy him a microphone for
his birthday, he actively forced his son to focus
on writing his own raps. He made him study the
craft. Wow, so he was really trained. Yeah, so
by the time Ski Mask is in juvie, trading ideas
and learning different rapping cadences from
X, he already has this deeply ingrained, highly
technical understanding of how to construct a
verse. He understands breath control, internal
rhyme schemes, and pocket. I do have to push
back a little here, though. Sure, go ahead. Because
if you look at the list of his actual musical
influences from the sources we're pulling from,
it is completely chaotic. Oh, it's all over the
place. Right. He cites Busta Rhymes, Missy Elliott,
Lil Wayne, and the Wu -Tang Clan, which, you
know, makes perfect sense for a rapper. Standard
hip hop foundation, yeah. But then he also says
he actively listens to classical music, heavy
metal, and, wait for it, Adele. Adele? Yeah,
Adele. So how on earth do you put heavy metal
Busta Rhymes and Adele into a blender and pour
out something that the industry labels meme rap
and SoundCloud rap? Like how does that actually
work musically? Well that tension is the exact
genius of that specific era of internet rap and
Ski Mask was the primary architect of how to
make it function. Okay break that down for me.
When you have influences that broad, you aren't
constrained by the traditional boundaries of
what hip -hop is supposed to sound like. To understand
how he did it, you really have to look at the
mechanics. Right. He took the rapid fire, triplet
vocal cadences of someone like Busta Rhymes,
but instead of putting it over a traditional
boom bat beat, he layered it over aggressive,
distorted, blown out 808 bass lines. Bass lines
that literally sound like your car speakers are
breaking. Exactly. It mimics the aggression and
the clipping distortion of punk rock or heavy
metal. It commands your attention because it
sounds dangerous. It has that edge to it. But
then he juxtaposes that heavy metal aggression
by sampling melancholic, melodic vocals, like
in a Dell track, or even ridiculous nostalgic
cartoon theme songs. Which is just so bizarre
when you think about it. It is. But that friction
between elite technical rapping, ear -shattering
bass, and weird, nostalgic samples is what creates
the sound. And that's where the term meme rap
comes in. But I think people really misunderstand
that label. Oh, so? They think it just means
funny rap. like parody music, but it was actually
about weaponizing internet culture, wasn't it?
Precisely. It was about hacking the algorithm.
By using obscure pop culture references, ridiculous
song titles, and recognizable cartoon samples,
Ski Mask was building an inside joke community
with his listeners. Sort of a if you know you
know vibe. Exactly. Aesthetically, he's wearing
these multicolored durags, presenting an image
that is deeply unserious on the surface. But
when you actually hit play, you were met with
lethal technical skill. It catches you off guard.
So he and X formed the collective, very rare,
and then co -found members only, and they just
start dropping these raw audio files on SoundCloud.
But this hyper -local, completely unpolished
energy cultivated down in Broward County, Florida,
didn't stay a local curiosity. It breached containment.
It absolutely exploded. Following his release
from GUVC, mass just starts flooding the internet.
We get the members -only volume 1 collaboration
mixtape with X in 2015, followed quickly by volumes
2 and 3. He was relentless with the output. As
a solo artist, he's dropping tracks that are
basically taking over the internet's underground.
Songs like Catch Me Outside, Life is Short, Baby
Wipe, and the massive anthem Take a Step Back,
featuring X. Which eventually goes gold. Right.
The momentum was staggering. By May 2016, he
drops his first mixtape. drown in designer. But
you can't just look at the streaming numbers,
you have to look at the network he was building.
Because he wasn't just insulated in Florida anymore.
Not at all. The features list alone tells you
how big this was getting. He's suddenly working
with Lil Pump, Denzel Curry, and Lil Peep. All
massive names in that scene. And he's doing tracks
with established stars like AAP Ferg, Lil Yachty,
and Offset. He's crossing international lines,
collaborating with artists from the 88 rising
label like the Higher Brothers and Keith Ape.
It was a global movement. And on top of all that,
he gets to work with his favorite producer, Timbaland.
That is a massive collision of different musical
subcultures. If we connect this to the bigger
picture, this specific run is the moment the
mainstream music industry establishment realizes
they can no longer ignore the internet. They
had to wake up. Ski Mask was proving that this
blown -out SoundCloud revolution, as Rolling
Stone called it, wasn't just a quirky teenage
fad. It was... highly commercially viable. Right.
It was generating millions of streams without
a traditional marketing budget. But wait, I'm
a little confused here. Okay, what's confusing?
If the entire appeal of SoundCloud Wrap is that
it's raw, unpolished, and completely anti -establishment,
doesn't... signing with a major label kill the
very authenticity that made him popular in the
first place? That is the danger, yes. Because
he bridges that gap. He goes from uploading raw
files on SoundCloud to signing with Victor, Victor
Worldwide, an imprint of Republic Records. How
did he survive that transition without his core
fans turning on him? That is the tightrope he
walked so well. He survived it because he didn't
compromise the core aesthetic. He just upgraded
the distribution pipeline. Oh, I see. When he
dropped his debut commercial mixtape, You will
regret. In June 2017, it still sounded like Ski
Mask. You still had that gritty feel. Exactly.
It still had the distorted bass and the cartoonish
energy, but now it had the muscle of Republic
Records to push it onto the Billboard 200. So
he didn't sell out his sound. No, he proved you
could take the raw DNA of the internet and package
it for the masses. By 2018, he is named to the
prestigious XXL freshman class. And it peaks
with his debut studio album, Stokely, released
in November 2018. It reaches number six on the
Billboard 200 chart. Huge accomplishment. It
gives us massive Hot 100 hits like Faucet Failure
and Nuketown, which featured a rising rapper
he had recently befriended named Juice World.
So from a purely career -oriented perspective,
he has achieved the impossible. He took a chaotic
underground culture, forced it into the mainstream
on his own terms, and successfully translated
viral fame into undeniable billboard dominance.
But if you look closely at the dates here, there
is a really disturbing collision between his
highest commercial highs and his absolute lowest
personal lows. Yeah, the timeline is rough. Here's
where it gets really interesting, but also incredibly
heartbreaking. Just as Ski Mask is hitting the
absolute peak of those Billboard charts, his
personal world is entirely shattered. The contrast
between his professional ascension and his personal
devastation during this roughly two year period
is genuinely difficult to comprehend. The timeline
is just brutal. So Ski and XXentation had an
incredibly intense bond. They were essentially
brothers who built an empire from a juvie cell,
but it was volatile. Very volatile. By late 2017,
they actually had a falling out and distanced
themselves to work on their own projects. They
needed space. But they eventually reunite in
May 2018 at the Rolling Loud Festival in Miami.
They hug on stage in front of thousands of people.
completely reaffirming their friendship. Of a
profoundly beautiful moment of public reconciliation.
It was, but then, barely a month later on June
18, 2018, XXXTentation is murdered. Yeah. And
the detail from the sources that just stops you
in your tracks. Ski Mask learned about his best
friend's death while he was actively broadcasting
on Instagram Live. Just wow. He had to tearfully
inform his own fans about it in real time. This
raises an important question about the human
capacity to process grief. when you are fundamentally
living your life in the public eye. Because there's
no off switch. Exactly. Because of the intense
parasocial relationship that internet fans have
with these artists, there was no private space
for Ski Mask to mourn. Everyone was watching.
His grieving process was live streamed to millions
of teenagers who were also grieving and looking
to him for a reaction. He wasn't just losing
a friend, he was losing a cultural icon alongside
millions of strangers. And almost immediately
he became this living memorial. After X's death,
Ski Mask made a point to honor him constantly
at his concerts, playing his songs, keeping his
energy alive. He really carried that weight.
The sources even note a deeply emotional moment
where he met X's son Gekyum for the first time
in person while at a show. Just incredible. But
the tragedy doesn't stop there. Let's look at
his relationship with the Juice World. They had
bonded deeply in early 2018. They made the massive
hit Nuketown together. They were so creatively
in sync that they even announced a joint mixtape
titled Evil Twins. Though it never officially
saw the light of day. Right. Sadly. But they
were inseparable. They were touring together
in 2019 on the death race for love tour alongside
Cole Bennett who directed a lot of their most
famous music videos and Then on December 8 2019
juice world dies from an accidental drug overdose
So within a span of roughly 18 months, he loses
his two best friends The two artists who, alongside
him, essentially defined that entire era of hip
hop are suddenly gone. And I think we need to
look at an additional layer of personal struggle
here that often gets overlooked in the shadow
of those tragedies. What's that? Right in the
middle of all of this, in March 2018, just months
before X was killed and right as his own solo
career was exploding, Ski Mask himself had a
heart condition that required surgery. At 22
years old. Exactly. And it makes you wonder,
is it possible that the hyperkinetic, invincible
cartoon energy of his music was actually a psychological
coping mechanism? That's a really interesting
point. Because the sheer volume of physical trauma
from having a failing heart, combined with the
devastating emotional trauma of losing your closest
brothers in a two -year window, it is staggering.
It's a fascinating theory. You have an artist
whose entire brand was built on carefree punk
rap rebellion. the music was about defying gravity.
Exactly. And suddenly he is weighed down by the
heaviest realities imaginable. His own mortality,
profound grief, and the overwhelming pressure
of being the one left behind to carry the torch.
Which naturally leads to the obvious question,
how does a person possibly move forward? When
the collaborators who defined your sound, your
rise, and your entire youth are suddenly gone,
How do you keep making the cartoon character
slip on the banana peel when the real world has
been so relentlessly cruel? For a while, the
output definitely slowed down, which is the most
natural human response. Of course. Following
that massive Stokely album in late 2018, he only
released one single in 2019. In 2020, he released
one single, Burn the Hoods. He was laying low.
He did drop the Sin City mixtape in 2021. a nod
to his father's stage name. But there were years
of relatively quiet periods. He needed time to
process the profound impact those deaths had
on his life and his art. But the story doesn't
end in that quiet period. Bringing us up to the
modern resurgence, looking at the years 2024
through 2026, we see that Ski Mask absolutely
did not quit. He came back incredibly strong.
He did. In June 2024, he released his highly
anticipated second studio album, 11th Dimension.
And what's really touching is that the project
features posthumous vocals from both XXXTentation
and Juice World, alongside current heavyweights
like Future and ATL Jacob. He literally carried
his brothers with him into his new era. He made
sure they were still part of the architecture
of his music. He absolutely did. And then we
see some massive business moves that completely
shift his trajectory. Like what? Well, early
in 2025, he signs a new deal with Empire Distribution.
On July 4th, 2025, he drops a sequel to one of
his biggest breakout hits, Catch Me Outside 2,
complete with a music video directed by his old
friend, Cole Bennett. It's a beautiful full circle
moment, bringing back the original team. Right.
But then, later that same month, on July 30,
2025, he drops a compilation album called The
Lost Files. This is released under his own new
label, Very Rare & Co., in partnership with Empire.
And the sources note that this album is comprised
of his older SoundCloud tracks that were previously
completely unavailable on major streaming services.
It even includes three early tracks with XXXTentation,
Fatality, Barolee, and I watched him drown. And
that detail right there. is the crucial turning
point of his modern career. So what does this
all mean? Why is an artist in 2025 releasing
a sequel to a 2017 song and spending time uploading
old, buried SoundCloud files instead of just
focusing entirely on the future? Because he is
no longer just a rapper. He has actively taken
on the role of a cultural archivist. An archivist,
okay. Think about your own experience with the
internet for a second. Think about a YouTube
video, a MySpace track, or a SoundCloud makes
you absolutely love 10 years ago. Oh man, yeah.
Half of them are gone. Exactly. If you try to
find it today, it's probably gone. The link is
dead. The account was deleted. The file is corroded.
We treat the internet like it's permanent, but
it's actually incredibly fragile. It really is.
That early meme rap era was born in a digital
Wild West full of uncleared samples and messy
uploads. Right. The digital evaporation of history.
Exactly. And Ski Mask is fighting against that
evaporation for his entire generation. By taking
those raw, nostalgic tracks, formally clearing
the samples, and officially putting them on major
streaming platforms through his own label, he
is essentially creating a digital seed vault.
Wow, a digital seed vault. I like that. He is
preserving the raw DNA of the SoundCloud era
against the inevitable link rot of the internet.
And we have to talk about the business mechanics
of that move, too, because forming your own label,
very rare in Co., to release these tracks in
partnership with empire distribution, that isn't
just nostalgia. No, it's a statement. That is
a massive power move. It represents an artist
taking back ownership of their master recordings
from that digital Wild West. He's not just an
employee of a major label anymore. He's an executive
ensuring that the foundation he and his friends
built doesn't just evaporate. He is formalizing
the history of a subculture that the mainstream
industry initially dismissed as just kids making
noise in their bedrooms. He's ensuring future
generations can still access the original source
code of the genre. And for you as the listener,
that is really the ultimate takeaway from the
story of Ski Mask, the slump god. It is an absolute
master class in human resilience. It truly is.
We so often look at internet culture as this
disposable machine that just churns out fleeting
memes, something to laugh at for 10 seconds,
swipe up, and then forget forever. Just endless
scrolling. Right. But Ski Mask's journey shows
how that exact same internet can also document
enduring deeply human perseverance. He survived
the juvenile justice system, he survived a terrifying
heart surgery at 22, and he survived the unimaginable
grief of losing his closest brothers while the
entire world was watching. It really leaves us
with a lingering, provocative question to ponder.
What's that? Well, we just analyze his vital
work as an archivist with the lost files. But
when the pioneers of a digital subculture are
tragically lost so young before they have the
chance to fully cement their own legacies, does
the responsibility of keeping that subculture's
history alive fall entirely on the shoulders
of the survivors? That is such a heavy burden.
It's an incredibly heavy burden to carry the
memory of an entire movement, ensuring that the
world remembers the brilliance of what you all
built together. It's a massive, almost unfair
burden. You start out as that cartoon character,
totally invincible, running on pure chaotic energy,
thinking you can hang in the air forever. But
eventually, the cartoon has to stop. The gravity
of the real world kicks in, and Stokely Goldberg
proved that when you finally hit the ground,
you can either let the crater swallow you entirely,
or you can climb out, dust off the multicolored
durag, and make absolutely sure the world never
forgets the artists who fell alongside you. Well
said. Thank you for joining us on this deep dive.
Next time you hear the chaotic, brilliant evolution
of ski mask sound, we hope you listen with these
new insights in mind.